(S)-2-butyl azide | 131491-44-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-2-butyl azide
• 英文别名: (+)(S)-2-azido-butane；(+)(S)-2-Azido-butan；(+)(S)-sek.-Butylazid；(2S)-2-azidobutane
• CAS: 131491-44-6
• 化学式: C₄H₉N₃
• 分子量: 99.1356
• InChiKey: WOAFFPVHLXPFEG-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-butyl azide 在 甲醇 、 platinum(IV) oxide 作用下， 生成 (S)-(+)-2-氨基丁烷
  参考文献：
  名称：

  Levene; Rothen, Journal of Biological Chemistry, 1936, vol. 115, p. 426

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(ethyl carbonic) (S)-2-methylbutanoic anhydride 在 sodium azide 作用下， 反应 0.5h， 生成 (S)-2-butyl azide
  参考文献：
  名称：

  Diener, Wolfgang; Frelek, Jadwiga; Snatzke, Guenther, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 5, p. 954 - 965

  摘要：

  DOI：

文献信息

• Chiral synthesis via organoboranes. 28. Reaction of .alpha.-chiral organyldichloroboranes with organyl azides providing a synthesis of secondary amines with exceptionally high enantiomeric purities
  作者：Herbert C. Brown、Ashok M. Salunkhe、Bakthan Singaram

  DOI：10.1021/jo00003a046

  日期：1991.2

  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.
• 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：——