3-(3'-indolyl)-(2S)-(N-methylamino)-1,1-di(2''-methylphenyl)-1-propanol | 171007-19-5

• 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: 3-(3'-indolyl)-(2S)-(N-methylamino)-1,1-di(2''-methylphenyl)-1-propanol
• 英文别名: (2S)-3-(1H-indol-3-yl)-2-(methylamino)-1,1-bis(2-methylphenyl)propan-1-ol
• CAS: 171007-19-5
• 化学式: C₂₆H₂₈N₂O
• 分子量: 384.521
• InChiKey: YIXBNYVDWVOLMS-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异丁醛 、 3-(3'-indolyl)-(2S)-(N-methylamino)-1,1-di(2''-methylphenyl)-1-propanol 在 4 A MS 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以85%的产率得到(2S,4S)-4-(1H-indol-3-ylmethyl)-3-methyl-5,5-bis(2-methylphenyl)-2-propan-2-yl-1,3-oxazolidine
  参考文献：
  名称：

  Chiral ligands derived from abrine. Part 5: Substituent effects on asymmetric induction in enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral oxazolidines possessing an indole moiety

  摘要：

  A number of the indole-containing chiral oxazolidines possessing the gem-di-p-tolyl and gem-di-o-tolyl groups at C-5 were synthesized from abrine and the effects of the C-5 and C-2 substituents on the asymmetric induction in catalytic enantioselective addition of diethylzinc to benzaldehyde were examined. A working model is proposed to rationalize the asymmetric catalysis by these chiral oxazolidines. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00298-5
• 作为产物：
  描述：

  相思豆毒素 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3'-indolyl)-(2S)-(N-methylamino)-1,1-di(2''-methylphenyl)-1-propanol
  参考文献：
  名称：

  Chiral ligands derived from Abrine. 1. Synthesis of sec- and tert-β-amino alcohols and catalysis for enantioselective addition of diethylzinc toward aromatic aldehydes

  摘要：

  DOI：

  10.1016/0957-4166(95)00236-i

文献信息

• 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
  作者：Wei-Min Dai、Hua-Jie Zhu、Xiao-Jiang Hao

  DOI：10.1016/s0957-4166(00)00189-0

  日期：2000.6

  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.
• 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
• Chiral ligands derived from abrine. Part 5: Substituent effects on asymmetric induction in enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral oxazolidines possessing an indole moiety
  作者：Hua-Jie Zhu、Bi-Tao Zhao、Wei-Min Dai、Jun Zhou、Xiao-Jiang Hao

  DOI：10.1016/s0957-4166(98)00298-5

  日期：1998.8

  A number of the indole-containing chiral oxazolidines possessing the gem-di-p-tolyl and gem-di-o-tolyl groups at C-5 were synthesized from abrine and the effects of the C-5 and C-2 substituents on the asymmetric induction in catalytic enantioselective addition of diethylzinc to benzaldehyde were examined. A working model is proposed to rationalize the asymmetric catalysis by these chiral oxazolidines. (C) 1998 Elsevier Science Ltd. All rights reserved.