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[ CAS No. 103733-65-9 ] {[proInfo.proName]}

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Chemical Structure| 103733-65-9
Chemical Structure| 103733-65-9
Structure of 103733-65-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 103733-65-9 ]

CAS No. :103733-65-9 MDL No. :MFCD00144038
Formula : C10H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BWKMGYQJPOAASG-SECBINFHSA-N
M.W : 177.20 Pubchem ID :712398
Synonyms :
D-phenylalanine analogue

Calculated chemistry of [ 103733-65-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.36
TPSA : 49.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : -1.33
Log Po/w (WLOGP) : 0.25
Log Po/w (MLOGP) : -1.2
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 0.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.38
Solubility : 74.5 mg/ml ; 0.42 mol/l
Class : Very soluble
Log S (Ali) : 0.79
Solubility : 1100.0 mg/ml ; 6.21 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.674 mg/ml ; 0.0038 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 103733-65-9 ]

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

Application In Synthesis of [ 103733-65-9 ]

* 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 [ 103733-65-9 ]
  • Downstream synthetic route of [ 103733-65-9 ]

[ 103733-65-9 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 307304-56-9 ]
  • [ 74163-81-8 ]
  • [ 103733-65-9 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7310 - 7322
  • 2
  • [ 50-00-0 ]
  • [ 673-06-3 ]
  • [ 103733-65-9 ]
YieldReaction ConditionsOperation in experiment
42% With hydrogenchloride In water at 20 - 95℃; for 6 h; Preparation 121: Phenylmethyl (3R) -1,2,3, 4-tetrahydroisoquinoline-3- carboxylate D-phenylALANINE (50 g, 0.3 mol) concentrated hydrochloric acid (386 ML), and formalin (37percent wt, 113.7 ml) were heated at 95 C with vigorous stirring for 4 h. The reaction mixture was cooled to room temperature and stirred for a further 2 h. The reaction mixture was filtered and the precipitate was washed with cold water to give (3R) -1,2,3, 4-tetrahydroisoquinoline-3-carboxylic acid as a white solid (25 g, 42percent). Benzyl alcohol (64 g) and P-TOLUenE SULPHONIC acid (26.9 g) were added and the reaction mixture was refluxed in benzene (400 mi) under Dean Stark conditions. The solvent was removed in vacuo, the crude residue was triturated with diethyl ether to give a solid which was then RECRYSTALLISED from water and methanol to give the title compound as a white solid (28 g, 35percent).
Reference: [1] MedChemComm, 2014, vol. 5, # 9, p. 1381 - 1383
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2092 - 2097
[3] Patent: WO2004/72086, 2004, A2, . Location in patent: Page 182
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5727 - 5737
  • 3
  • [ 146503-35-7 ]
  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
  • 4
  • [ 143767-57-1 ]
  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
  • 5
  • [ 307304-64-9 ]
  • [ 103733-65-9 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7310 - 7322
  • 6
  • [ 612-12-4 ]
  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
[2] Synthesis, 1992, # 11, p. 1157 - 1160
  • 7
  • [ 143767-55-9 ]
  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
[2] Synthesis, 1992, # 11, p. 1157 - 1160
  • 8
  • [ 67123-97-1 ]
  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
  • 9
  • [ 143767-54-8 ]
  • [ 103733-65-9 ]
Reference: [1] Synthesis, 1992, # 11, p. 1157 - 1160
  • 10
  • [ 307304-56-9 ]
  • [ 74163-81-8 ]
  • [ 103733-65-9 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7310 - 7322
  • 11
  • [ 74163-81-8 ]
  • [ 103733-65-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 12, p. 3729 - 3731
  • 12
  • [ 103733-65-9 ]
  • [ 191327-28-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4833 - 4837
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