(S)-3-hex-1-enylamine | 63731-09-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-3-hex-1-enylamine
• 英文别名: (S)-3-amino-1-hexene；1-Hexen-3-amine, (S)-；(3S)-hex-1-en-3-amine
• CAS: 63731-09-9
• 化学式: C₆H₁₃N
• 分子量: 99.1759
• InChiKey: WYAKBMRDDZSEPR-ZCFIWIBFSA-N

物化性质

• 沸点：
  129.7±9.0 °C(Predicted)
• 密度：
  0.782±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙烯基乙酸 、 (S)-3-hex-1-enylamine 在 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以2.6 g的产率得到(S)-N-(hex-1-en-3-yl)but-3-enamide
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w
• 作为产物：
  描述：

  (S)-2,2,2-trichloro-N-(1-propylallyl)acetamide 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 (S)-3-hex-1-enylamine
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w

文献信息

• Catalytic Asymmetric Rearrangement of Allylic <i>N</i>-Aryl Trifluoroacetimidates. A Useful Method for Transforming Prochiral Allylic Alcohols to Chiral Allylic Amines
  作者：Larry E. Overman、Carolyn E. Owen、Mary M. Pavan、Christopher J. Richards

  DOI：10.1021/ol0271786

  日期：2003.5.1

  useful method for the conversion of prochiral allylic alcohols to chiral allylic amines of high enantiopurity is reported. N-(4-Methoxyphenyl)trifluoroacetimidates are excellent substrates for the palladium(II)-catalyzed allylic imidate rearrangement as the allylic trifluoroacetamide products can be deprotected in two steps to provide chiral nonracemic allylic amines. Di-mu-chlorobis[(eta(5)-(S)-(pR)-

  [反应：见正文]报道了一种将前手性烯丙基醇转化为高对映体纯度的手性烯丙基胺的有用方法。N-（4-甲氧基苯基）三氟乙亚胺酸酯是钯（II）催化的烯丙基亚氨酸酯重排的极好的底物，因为烯丙基三氟乙酰胺产物可在两个步骤中脱保护以提供手性非外消旋烯丙基胺。Di-mu-chlorobis [[（eta（5）-（S）-（pR）-2-（2'-（4'-异丙基））恶唑啉基环戊二烯基，1-C，3'-N））（eta（4） -四苯基环丁二烯（钴）二钯（6a，COP-Cl）是一种优异的催化剂，因为它不需要用银盐活化，并以高收率和高对映体纯度提供了重排的烯丙基三氟乙酰胺。
• Ringdahl, Bjoern, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 2, p. 141 - 152
  作者：Ringdahl, Bjoern

  DOI：——

  日期：——
• Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles
  作者：Hiroshi Nomura、Christopher J. Richards

  DOI：10.1021/ol900880w

  日期：2009.7.2

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.