(2S)-amino-3-(3'-indolyl)-1,1-diphenyl-1-propanol | 154721-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-amino-3-(3'-indolyl)-1,1-diphenyl-1-propanol
• 英文别名: (S)-1,1-diphenyltryptophanol
• CAS: 154721-38-7
• 化学式: C₂₃H₂₂N₂O
• 分子量: 342.44
• InChiKey: IGWXTCSCHGORPI-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.04
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S)-amino-3-(3'-indolyl)-1,1-diphenyl-1-propanol 在 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 88.0h， 生成
  参考文献：
  名称：

  现成的氢键催化剂可用于硝基烯烃的不对称转移氢化†

  摘要：

  本文着重于易于访问的内容 硫脲衍生自氨基酸的氢键催化剂，其位阻和电子特征受其在甲醇碳中心的取代度的调节。这些催化剂被用于硝基烯烃的不对称转移氢化，从而以高达99％的收率和86％的对映体过量提供手性产物。所提出的催化剂的作用方式得到机理研究的支持。

  DOI：

  10.1039/c1ob05059a
• 作为产物：
  描述：

  苯基氯化镁 、 L-色氨酸甲酯盐酸盐 以 四氢呋喃 为溶剂， 反应 19.0h， 以60%的产率得到(2S)-amino-3-(3'-indolyl)-1,1-diphenyl-1-propanol
  参考文献：
  名称：

  Chiral ligands derived from abrine. Part 6: Importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes

  摘要：

  A number of chiral beta-amino alcohols possessing a 3-indolylmethyl group have been synthesized from the alkaloid (S)-abrine and elucidated for potency in the catalytic enantioselective ethylation of PhCHO with Et2Zn. In general, the secondary amines 15a-d bearing a dialkylhydroxymethyl group induced (R)-1-phenyl-1-propanol, whereas 15e-g and 18 bearing a diarylhydroxymethyl group favored the (S)-enantiomer. In contrast, the beta-tertiary amino alcohols 20b d and 21 produced (R)-1-phenyl-1-propanol. regardless of the substituents at the carbon bearing the hydroxy group. Enantiomeric excess of 87.5% was obtained for (R)-1-phenyl-1-propanol using ligand 21 as the promoter. Eleven substituted benzaldehydes and naphth-aldehydes were examined for enantioselective ethylation by using 21 and the chiral alcohols were obtained in 93-97% ee, except for o-BrC6H4CHO and p-Me2NC6H4CHO. Excellent enantioselectivity was also observed in the ethylation of cyclohexanecarboxaldehyde (94.8% ee) and 2-thiophenecarboxaldehyde (94.9% ee) by using catalytic 21. The anti 5/4/4-fused tricyclic TS I was proposed to rationalize the asymmetric induction. The diethylhydroxymethyl and N-2-t-butylethyl groups are believed to enforce the preference for the anti-TS(R) I and it results in high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00189-0

文献信息

• Highly Efficient Organocatalyzed Direct Asymmetric Aldol Reactions of Hydroxyacetone and Aldehydes
  作者：Xiaoyu Wu、Zhixiong Ma、Zhengqing Ye、Shan Qian、Gang Zhao

  DOI：10.1002/adsc.200800558

  日期：2009.1

  Novel organocatalysts derived from L-threonine and L-leucine have been synthesized for catalyzing direct aldol reactions of hydroxycetone and unactivated aliphatic aldehydes with as low as 2 mol% loading of the catalyst, good to excellent yields and excellent enantioselectivities have been achieved for aliphatic aldehydes, whereas aromatic aldehydes yield only moderate enantioselectivities.

  合成了衍生自L-苏氨酸和L-亮氨酸的新型有机催化剂，用于催化羟基丙酮与未活化的脂族醛的直接醛醇缩合反应，催化剂的负载量低至2 mol％，对脂族醛具有良好至优异的收率和优异的对映选择性。 ，而芳族醛仅产生中等对映选择性。
• Chiral ligands derived from Abrine. 1. Synthesis of sec- and tert-β-amino alcohols and catalysis for enantioselective addition of diethylzinc toward aromatic aldehydes
  作者：Wei-Min Dai、Hua Jie Zhu、Xiao-Jiang Hao

  DOI：10.1016/0957-4166(95)00236-i

  日期：1995.8
• Dammast, Franziska; Reissig, Hans-Ulrich, Chemische Berichte, 1993, vol. 126, # 11, p. 2449 - 2456
  作者：Dammast, Franziska、Reissig, Hans-Ulrich

  DOI：——

  日期：——