1,1-diethyl-3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-1-propanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,1-diethyl-3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-1-propanol
• 英文别名: (S)-2-[(3,3-dimethylbutyl)(methyl)amino]-3-ethyl-1-(1H-indol-3-yl)pentan-3-ol；(2S)-2-[3,3-dimethylbutyl(methyl)amino]-3-ethyl-1-(1H-indol-3-yl)pentan-3-ol
• 化学式: C₂₂H₃₆N₂O
• 分子量: 344.541
• InChiKey: WZRVMJYKAXJSOR-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  相思豆毒素 在 lithium aluminium tetrahydride 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 92.0h， 生成 1,1-diethyl-3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-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
• 作为试剂：
  描述：

  3,5-二甲氧基苯甲醛 、 diethylzinc 在 1,1-diethyl-3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-1-propanol 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 116.0h， 生成 (R)-1-(3',5'-dimethoxyphenyl)-1-propanol 、 (S)-1-(3’,5’-dimethoxyphenyl)-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

• 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 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.