3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutyrylamino)-1,1-di(4'''-methylphenyl)-1-propanol | 171007-26-4

• 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: 3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutyrylamino)-1,1-di(4'''-methylphenyl)-1-propanol
• CAS: 171007-26-4
• 化学式: C₃₂H₃₈N₂O₂
• 分子量: 482.666
• InChiKey: VRRNONRAYAMWBG-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  56.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutyrylamino)-1,1-di(4'''-methylphenyl)-1-propanol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以65%的产率得到3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-1,1-di(4'''-methylphenyl)-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
• 作为产物：
  描述：

  相思豆毒素 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutyrylamino)-1,1-di(4'''-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