N-<(3S)-3,7-dimethyloct-6-enyl>-(1S,2S)-trans-2-methylcyclohexylamine | 131491-39-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-<(3S)-3,7-dimethyloct-6-enyl>-(1S,2S)-trans-2-methylcyclohexylamine
• 英文别名: (1S,2S)-N-[(3S)-3,7-dimethyloct-6-enyl]-2-methylcyclohexan-1-amine
• CAS: 131491-39-9
• 化学式: C₁₇H₃₃N
• 分子量: 251.456
• InChiKey: FASNRJNYXXGHER-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  <(1S,2S)-trans-2-methylcyclohexyl>dichloroborane-dimethylsulfide 、 (3S)-3,7-dimethyloct-6-enyl azide 在 水 作用下， 生成 N-<(3S)-3,7-dimethyloct-6-enyl>-(1S,2S)-trans-2-methylcyclohexylamine
  参考文献：
  名称：

  Chiral synthesis via organoboranes. 28. Reaction of .alpha.-chiral organyldichloroboranes with organyl azides providing a synthesis of secondary amines with exceptionally high enantiomeric purities

  摘要：

  2-Alkyl-1,3,2-dioxaborinanes R*BO2(CH2)3 of essentially 100% enantiomeric purity were prepared by the asymmetric hydroboration of readily available prochiral olefins with mono- or diisopinocampheylboranes, followed by removal of the chiral auxiliary (alpha-pinene). The intermediate R*BO2(CH2)3 reacts readily with lithium aluminum hydride at 0-degrees-C to give the corresponding lithium monoalkylborohydrides stereospecifically in very good yields and in very high enantiomeric purities. The lithium monoalkylborohydrides, on treatment with hydrogen chloride in dimethyl sulfide, give the corresponding monoalkyldichloroboranes in very high enantiomeric purity. The intermediate monoalkyldichloroboranes react readily with organic azides in 1,2-dichloroethane with evolution of gaseous nitrogen and transfer of the organic group from boron to nitrogen with complete retention of configuration to provide the corresponding secondary amines, either (+)- or (-), in very high yields and exceptionally high enantiomeric purities. The procedure was applied to the synthesis of representative optically active amines of high enantiomeric purities (ee or de greater-than-or-equal-to 99%), including (2S,2'S)-di-2-butylamine, N-[(2S)-2-methyl-1-butyl]-(1S,2R)-trans-2-phenycyclopentylamine, N-[(3S)-3,7-dimethyloct-6-enyl](1S,2S)-trans-2-methylcyclohexylamine, and the meso-di-2-butylamine.

  DOI：

  10.1021/jo00003a046

文献信息

• BROWN, HERBERT C.;SALUNKHE, ASHOK M.;SINGARAM, BAKTHAN, J. ORG. CHEM., 56,(1991) N, C. 1170-1175
  作者：BROWN, HERBERT C.、SALUNKHE, ASHOK M.、SINGARAM, BAKTHAN

  DOI：——

  日期：——