(+/-)-threo-3-Amino-1,2-diphenyl-propanol-(1) | 13286-62-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-threo-3-Amino-1,2-diphenyl-propanol-(1)
• 英文别名: (1S,2S)-3-amino-1,2-diphenylpropan-1-ol
• CAS: 13286-62-9；13440-23-8；92646-34-9
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: VPURFUWIEYPVIL-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-threo-3-Amino-1,2-diphenyl-propanol-(1) 、 2-巯基-S-硫代苯甲酰乙酸 在 吡啶 作用下， 生成 (+-)-threo-3-Thiobenzamino-1,2-diphenyl-propanol-(1)
  参考文献：
  名称：

  Drefahl,G.; Hoerhold,H.-H., Chemische Berichte, 1961, vol. 94, p. 1641 - 1656

  摘要：

  DOI：
• 作为产物：
  描述：

  3-hydroxy-2,3-diphenylpropionitrile 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 (+/-)-threo-3-Amino-1,2-diphenyl-propanol-(1)
  参考文献：
  名称：

  Synthesis of a potent wide-spectrum serotonin-, norepinephrine-, dopamine-reuptake inhibitor (SNDRI) and a species-selective dopamine-reuptake inhibitor based on the gamma-amino alcohol functional group

  摘要：

  A series of gamma-amino alcohols were synthesized and screened for reuptake inhibition and noncompetitive NMDA antagonism. Compound (+/-)-3f simultaneously and potently inhibits reuptake of 5-HT, NE, and DA, representing a potential wide-spectrum reuptake inhibitor antidepressant. In addition, comparative rat and human studies uncovered a species-selective DA reuptake inhibitor (+/-)-2e, K(D)(kDAT)/K(D)(rDAT) = 97. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00062-6

文献信息

• Anti-Selective Aldol Reaction of Benzylic Nitriles and Synthesis of .gamma.-Amino Alcohols
  作者：Paul R. Carlier、Kam Moon Lo、Michael M-C. Lo、Ian D. Williams

  DOI：10.1021/jo00128a025

  日期：1995.11

  The stereochemistry of the aldol reaction of seven benzylic nitriles 1a-g and four aldehydes 2-5 has been studied. In all cases studied the reaction is anti-selective. Good to excellent selectivity (10:1->20:1) can be obtained if aldehydes with bulky secondary or tertiary substituents are used. The resulting aldols 6-9 are easily transformed to the corresponding gamma-amino alcohols 12-15, which may possess useful antidepressant activity.
• Drefahl,G.; Hoerhold,H.-H., Chemische Berichte, 1961, vol. 94, p. 1641 - 1656
  作者：Drefahl,G.、Hoerhold,H.-H.

  DOI：——

  日期：——
• Synthesis of a potent wide-spectrum serotonin-, norepinephrine-, dopamine-reuptake inhibitor (SNDRI) and a species-selective dopamine-reuptake inhibitor based on the gamma-amino alcohol functional group
  作者：Paul R. Carlier、Michael M-C. Lo、Priscilla C-K. Lo、Elliott Richelson、Masahiko Tatsumi、Ian J. Reynolds、Terre A. Sharma

  DOI：10.1016/s0960-894x(98)00062-6

  日期：1998.3

  A series of gamma-amino alcohols were synthesized and screened for reuptake inhibition and noncompetitive NMDA antagonism. Compound (+/-)-3f simultaneously and potently inhibits reuptake of 5-HT, NE, and DA, representing a potential wide-spectrum reuptake inhibitor antidepressant. In addition, comparative rat and human studies uncovered a species-selective DA reuptake inhibitor (+/-)-2e, K(D)(kDAT)/K(D)(rDAT) = 97. (C) 1998 Elsevier Science Ltd. All rights reserved.