2-chloro-2-methyl-N-prop-2-enylpropan-1-imine | 128970-52-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-2-methyl-N-prop-2-enylpropan-1-imine
• CAS: 128970-52-5
• 化学式: C₇H₁₂ClN
• 分子量: 145.632
• InChiKey: HSNRNDGKAZEAOE-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-chloro-2-methyl-N-prop-2-enylpropan-1-imine 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 17.0h， 以83%的产率得到(2-Methyl-propenyl)-prop-2-en-(E)-ylidene-amine
  参考文献：
  名称：

  1,4-Dehydrochlorination of α-chloroimines as a suitable procedure for the synthesis of unactivated 2-aza-1,3-dienes and 3-aza-1,3,5-trienes

  摘要：

  DOI：

  10.1016/s0040-4039(00)94695-1
• 作为产物：
  描述：

  2-氯-2-甲基丙醛 、 丙烯胺 在 magnesium sulfate 作用下， 生成 2-chloro-2-methyl-N-prop-2-enylpropan-1-imine
  参考文献：
  名称：

  Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines

  摘要：

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.

  DOI：

  10.1021/jo040161b

文献信息

• Electrophile-Induced Ring Expansions of <i>β</i>-Lactams toward γ-Lactams
  作者：Willem Van Brabandt、Norbert De Kimpe

  DOI：10.1021/jo0509556

  日期：2005.10.1

  was developed from 4-(1-chloroalkyl)azetidin-2-ones. Starting from the latter β-lactams, a new synthesis of pyrrolidin-2-ones was achieved. When 4-isopropenylazetidin-2-ones were treated with bromine in dichloromethane, diastereoselective electrophile-induced ring expansions toward 5-bromopyrrolidin-2-ones were performed. Further oxidation of 3-benzyloxypyrrolidin-2-ones with bromine toward 3-bromopyrrolidin-2-ones

  从4-（1-氯烷基）氮杂环丁烷-2-酮开发了一种有效而直接的向3,4-顺-4-异丙烯基氮杂环丁烷-2-酮的途径。从后者的β-内酰胺开始，实现了吡咯烷-2-酮的新合成。当将4-异丙烯基氮杂环丁烷-2-酮用溴在二氯甲烷中处理时，进行了非对映选择性亲电试剂诱导的向5-溴吡咯烷酮-2-酮的环扩展。还确定了3-苄氧基吡咯烷-2-酮进一步被溴氧化成3-溴吡咯烷-2-酮。当将4-异丙烯基-β-内酰胺添加到NBS和TMSN 3的混合物中时，以中等至高收率获得了5-叠氮基吡咯烷酮-2-酮。
• Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines
  作者：Yves Dejaegher、Norbert De Kimpe

  DOI：10.1021/jo040161b

  日期：2004.9.1

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.
• 1,4-Dehydrochlorination of α-chloroimines as a suitable procedure for the synthesis of unactivated 2-aza-1,3-dienes and 3-aza-1,3,5-trienes
  作者：Norbert De Kimpe、Yao Zi-Peng、Marc Boeykens、Milan Nagy

  DOI：10.1016/s0040-4039(00)94695-1

  日期：1990.1