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[ CAS No. 132335-44-5 ] {[proInfo.proName]}

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Chemical Structure| 132335-44-5
Chemical Structure| 132335-44-5
Structure of 132335-44-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 132335-44-5 ]

CAS No. :132335-44-5 MDL No. :MFCD07782107
Formula : C9H15NOS Boiling Point : -
Linear Structure Formula :- InChI Key :XWCNSHMHUZCRLN-QMMMGPOBSA-N
M.W : 185.29 Pubchem ID :9964277
Synonyms :

Calculated chemistry of [ 132335-44-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.57
TPSA : 51.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 1.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.78
Solubility : 3.1 mg/ml ; 0.0167 mol/l
Class : Very soluble
Log S (Ali) : -1.86
Solubility : 2.55 mg/ml ; 0.0138 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.61 mg/ml ; 0.00869 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 132335-44-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 132335-44-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 132335-44-5 ]
  • Downstream synthetic route of [ 132335-44-5 ]

[ 132335-44-5 ] Synthesis Path-Upstream   1~15

  • 1
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Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 5, p. 854 - 856
[2] Patent: WO2009/87463, 2009, A2, . Location in patent: Page/Page column 7-8
  • 2
  • [ 321-38-0 ]
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 45, p. 7101 - 7104
  • 3
  • [ 13196-35-5 ]
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YieldReaction ConditionsOperation in experiment
80% With potassium <i>tert</i>-butylate; hydrogen In isopropyl alcohol; <i>tert</i>-butyl alcohol at 28℃; for 6 h; (Example 23)
Synthesis of (S)-3-N,N-dimethylamino-1-(2-thienyl)-1-propanol
trans-RuCl2((R)-xylBINAP)((R)-DAIPEN) (30.5 mg, 0.025 mmol), a 2-propanol solution (100 ml), a t-butanol solution (7.5 ml, 7.5 mmol) of 1.0M t-butoxy potassium and 3-(N-dimethylamino)-1-(2-thienyl)-1-propanone (22.9 g, 0.125 mol) were charged in a glass autoclave and, after repeatedly conducting deaeration and replacement by argon, hydrogen was introduced to a predetermined pressure, thereby to initiate the reaction.
After stirring at 28°C for 6 hours, the reaction solution was returned to normal temperature and normal pressure.
After the reaction solution was concentrated, heptane was added and the deposited solid was filtered with suction.
The resulting solid was dried under reduced pressure to obtain the objective compound.
The amount of the objective compound was 18.5 g (yield: 80.0percent).
Optical purity of the resulting compound was determined by the HPLC process using an optically active column.
As a result, optical purity was high such as 99percent ee.
(R)-DAIPEN denotes (R)-1-isopropyl-2,2-di(p-methoxyphenyl)ethylenediamine, and xylBINAP denotes 2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl.
Reference: [1] Patent: EP1506965, 2005, A1, . Location in patent: Page/Page column 35
[2] Angewandte Chemie (International ed. in English), 2004, vol. 43, # 21, p. 2816 - 2819
[3] Chemistry - A European Journal, 2011, vol. 17, # 28, p. 7760 - 7763
[4] Patent: US8426178, 2013, B2, . Location in patent: Page/Page column
[5] Chemical Communications, 2015, vol. 51, # 61, p. 12328 - 12331
[6] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 122, p. 44 - 50
[7] Patent: KR2015/43955, 2015, A,
  • 4
  • [ 13636-02-7 ]
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YieldReaction ConditionsOperation in experiment
34% With (S)-Mandelic acid In methanol; toluene at 20 - 95℃; for 1.5 h; The racemic mixture (2.92 g, 15.7mmol) was taken up in toluene (29mL) and methanol (0.73mL) in.To this clear solution was added S- mandelic acid at room temperature (1.10 g, 7.2mmol, 0.46 eq).The suspension was heated to 95 ° C for 1.5 hours, then cooled to room temperature.The white precipitate was filtered and the (10ml) and washed once with toluene.Under vacuum at 50 deg.] C to this white solid was dried for 12 hours.The white solid was then taken up in 2N sodium hydroxide (200 mL) and the mixture was extracted with MTBE (3x80mL).The combined organics were washed with water and brine, and dried over sodium sulfate.Filtered and concentrated under reduced pressure to give 0.98 g (34percent) of S- alcohol 3 as a white solid
Reference: [1] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[2] Patent: CN105566284, 2016, A, . Location in patent: Paragraph 0245; 0252
[3] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[4] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[5] Patent: CN104803968, 2017, B,
[6] Patent: CN104829587, 2017, B,
[7] Patent: CN104829587, 2017, B,
[8] Patent: CN107488163, 2017, A,
  • 5
  • [ 13196-35-5 ]
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YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide In isopropyl alcohol at 20℃; for 4 h; A mixture of [(1S,] [2R)-(-)-CIS-1-AMINO-2-INDANOL] (15.1 mg, 0.101 mmol), [(P-CYMENE)-] ruthenium (II) chloride dimer (15.6 mg, 0.026 mmol) and degassed isopropanol (8 mL) was stirred for 20 min at [85 C] under nitrogen atmosphere and then cooled to [20 C.] This solution was added to a mixture [OF 3-N, N-DIMETHYLAMINO-1-(2-THIENYL)-1-PROPANONE] (1. 83 g, 10.00 mmol), potassium hydroxide (0.1 N solution in isopropanol, 2.5 mL, 0.25 mmol) and degassed isopropanol (90 mL). The reaction mixture was stirred for 4 h at [20 C] under nitrogen atmosphere. After this time, the starting material, 3-N, N-dimethyl- [AMINO-1- (2-THIENYL)-1-PROPANONE,] had completely reacted (as determined [BYAPOS;H-NMR).][(S)-3-N, N-DIMETHYLAMINO-1-(2-THIENYL)-1-PROPANOL] having an e. e. of 67.5percent (as determined by chiral HPLC) was formed in a yield of 70percent (as determined [BYAPOS;H-NMR).]
9 % ee
Stage #1: With dimethylsulfide borane complex; C27H26BNO3 In tetrahydrofuran at 20℃; for 6.1 h;
Stage #2: at 80℃; for 20 h;
Cat-8 (0.1 mmol, 43 mg) prepared in PreparationExample 2.8 was dissolved in 2 mL of THF, BH3-DMS (0.80 mmol, 0.08 mL) wasadded, and the mixture was stirred for about 7 minutes. A solution of3-dimethylamino-1- (2-thienyl) -1-propanone (1.14 mmol, 210 mg) in 0.45 ml ofTHF was added dropwise to the reaction mixture dropwise over 5 minutes. After 6hours of reaction at room temperature, 5 ml of methanol was added to terminatethe reaction, and the mixture was heated at 80 ° C for 20 hours. (S)-3-dimethylamino-1- (2-thienyl) -1-propanol (yield: 74percent, 9percent ee) was obtained inthe same manner as in Example 3.3.
Reference: [1] Patent: WO2004/31168, 2004, A2, . Location in patent: Page 15-16
[2] Organic Letters, 2000, vol. 2, # 12, p. 1749 - 1751
[3] Patent: KR2015/43955, 2015, A, . Location in patent: Paragraph 0185; 0197-0199
  • 6
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YieldReaction ConditionsOperation in experiment
89% With potassium iodide In methanol; water at 80℃; for 8 h; (S) -3-chloro-1- (2-thienyl) -1-propanol (200 mg, 1.13 mmol) A 50percent aqueous solution of dimethylamine (1.7 mL, 18 mmol),A solution of methanol (2 mL) KI (19 mg, 0.1 mmol) was added to the mixed solution,And the mixture was refluxed at 80 DEG C for 8 hours. When the reaction was completed, the methanol was removed, and 1N aqueous NaOH solution (2 mL) was added to the residue, followed by extraction with ethyl acetate (3 mL).The extracted organic layer was dried over sodium sulfate and concentrated. The concentrated reaction product was purified by silica column chromatography (hexane: ethyl acetate = 3: 1) to obtain a solid (S) -3-dimethylamino-1- (2-thienyl) -1-propanol (187 mg, 89percent).
Reference: [1] Patent: KR2016/44117, 2016, A, . Location in patent: Paragraph 0097-0099
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YieldReaction ConditionsOperation in experiment
92.1% With glucose dehydrogenase; D-glucose; Rhodosporidium toruloides carbonyl reductase 9 from Escherichia coli; NADPH; sodium hydroxide In aq. phosphate buffer at 30℃; for 4 h; Enzymatic reaction In a 2-L bioreactor, 2a (1000mM), glucose (6000mM), NADP+ (0.75mM), and sonicated cells of co-expressing E. coli/RtSCR9-GDH (10gDCWL−1) were mixed in a total volume of 1L phosphate buffer (100mM, pH 7.0). The resulting mixture was stirred at 30°C with 200rpm shaking for 240min. The pH was maintained at 7.0 with 2M NaOH during the reaction. After reaching completion, the pH was adjusted to 11–12 followed by extraction using ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and concentrated to give (S)- 3a. Yield: 92.1percent. 1H NMR (500MHz, DMSO-d6): δ=7.36 (dd, J=4.9, 1.2Hz, 1H), 6.93 (m, 2H), 5.79 (s, 1H), 4.86 (m, 1H), 2.30 (qt, J=12.0, 7.1Hz, 2H), 2.12 (s, 6H), 1.79 (m, 2H). 13C NMR (126MHz, DMSO-d6): δ=150.72, 126.40, 123.79, 122.51, 67.39, 55.96, 45.15, 36.92. [α]25D=−4.9° (c=10mg/mL, ethyl acetate).
Reference: [1] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[2] Patent: US2005/197503, 2005, A1, . Location in patent: Page/Page column 4
[3] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[4] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[5] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[6] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[7] Patent: CN105566284, 2016, A,
[8] Patent: JP2017/19727, 2017, A, . Location in patent: Paragraph 0053
[9] Patent: CN104803968, 2017, B,
[10] Patent: CN104829587, 2017, B,
[11] Patent: CN104829587, 2017, B,
  • 8
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YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In water for 0.5 h; The ratio by mass of N,N-dimethylamino-1-(2-thienyl)-1-propanol:S-mandelic acid was 1.0:0.51. The mass of N,N-dimethylamino-1-(2-thienyl)-1-propanol was 18.5 g and S-mandelic acid was 7.7 g.N,N-dimethylamino-1-(2-thienyl)-1-propanol was added to the reaction flask, methyl tert-butyl ether 100 mL was added, stirring was started, and an ethanol solution in which S-mandelic acid was dissolved was added. 50mL, immediately a large number of white solids precipitated, heated to reflux for 1h, cooled to room temperature and stirred for 1h, suction filtration, to give a white solid (R)-3-N,N-dimethylamino-1-(2-thienyl)- 1-propanol-S-mandelic acid. Then, the salt was dissolved in water, and 10N sodium hydroxide was added dropwise to adjust the pH to 11 to 12. A large amount of solids precipitated. After stirring for 30 minutes, the solution was crystalized, filtered, and dried to obtain (S)-3 shown in (I). -N,N-Disubstituted amino-1-(2-thienyl)-1-propanol crude product 8.6 g, yield 93percent.The crude product of (S)-3-N,N-disubstituted amino-1-(2-thienyl)-1-propanol and ethyl acetate were charged at a mass ratio of 1:2, and the mixture was stirred and warmed up to 55° C. and dissolved completely. Then add 5percent activated carbon to decolorize, heat filter, and perform heat preservation and crystallization at -5~-10°C. Filtration, drying pure product 8.2g, yield 95percent.
92.1% With ammonium hydroxide In tert-butyl methyl ether 250 ml four-necked flask was added 8.1 g (S)-(-)-N,N-dimethyl-3-(2-thienyl)-3-hydroxypropylamine S-mandelate (I) obtained in Example 4 and 50 ml of tert-butyl methyl ether,3.6 g of 23percent aqueous ammonia (48.7 mmole) was added with stirring, stirred and neutralized to collect the organic layer. After the water was concentrated, the viscous material was concentrated and the viscous material was added with 15 ml of ethanol. The water was concentrated again and the residue was dissolved in 10 ml of ethanol and used in Example 6 as a resolving agent. The organic layer was washed with 10 ml of brine and concentrated under reduced pressure to give 4.1 g of product (S)- (-)-N,N-dimethyl-3-(2-thienyl)-3-hydroxypropylamine in a yield of 92.1percent Chiral Analysis: S-configuration: 98.3percent R Configuration: 1.7percent.
Reference: [1] Patent: CN107488163, 2017, A, . Location in patent: Paragraph 0043; 0044; 0045
[2] Patent: CN104803968, 2017, B, . Location in patent: Paragraph 0037; 0052; 0053
[3] Patent: US2008/15363, 2008, A1, . Location in patent: Page/Page column 6
[4] Patent: WO2008/4191, 2008, A2, . Location in patent: Page/Page column 7
[5] Patent: WO2008/93360, 2008, A2, . Location in patent: Page/Page column 9-13
[6] Patent: WO2009/19719, 2009, A2, . Location in patent: Page/Page column 16-17
[7] Patent: WO2009/19719, 2009, A2, . Location in patent: Page/Page column 17
[8] Patent: WO2010/79404, 2010, A2, . Location in patent: Page/Page column 7
[9] Patent: US2007/281989, 2007, A1, . Location in patent: Page/Page column 5
[10] Patent: US2010/280093, 2010, A1, . Location in patent: Page/Page column 3
[11] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
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Reference: [1] Patent: WO2007/77580, 2007, A2, . Location in patent: Page/Page column 16; 17
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 45, p. 7101 - 7104
[2] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[3] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[4] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[5] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[6] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[7] Patent: CN105566284, 2016, A,
[8] Patent: CN104829587, 2017, B,
[9] Patent: CN104829587, 2017, B,
[10] Patent: CN107488163, 2017, A,
  • 11
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Reference: [1] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[2] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[3] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[4] Organic Process Research and Development, 2006, vol. 10, # 5, p. 905 - 913
[5] Patent: CN104803968, 2017, B,
[6] Patent: CN104829587, 2017, B,
  • 12
  • [ 5424-47-5 ]
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 45, p. 7101 - 7104
[2] Tetrahedron Letters, 1990, vol. 31, # 45, p. 7101 - 7104
  • 13
  • [ 13636-02-7 ]
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Reference: [1] Bioorganic Chemistry, 2016, vol. 65, p. 82 - 89
[2] Molecules, 2016, vol. 21, # 11,
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Reference: [1] Patent: KR2016/44117, 2016, A,
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Reference: [1] Patent: CN107488163, 2017, A,
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