ethyl 2-cyclopropyl-2-[ethyl(p-methoxyphenyl)amino]-4-pentenoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-cyclopropyl-2-[ethyl(p-methoxyphenyl)amino]-4-pentenoate
• 英文别名: ethyl 2-cyclopropyl-2-[ethyl(4-methoxyphenyl)amino]-4-pentenoate；ethyl 2-cyclopropyl-2-(N-ethyl-4-methoxyanilino)pent-4-enoate
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: DYGRACVNXCNEKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-cyclopropyl-2-oxoacetate 在 对甲苯磺酸 、 过氧化苯甲酰 作用下， 以 正己烷 、 苯 为溶剂， 反应 27.0h， 生成 ethyl 2-cyclopropyl-2-[ethyl(p-methoxyphenyl)amino]-4-pentenoate
  参考文献：
  名称：

  Tandem N-Alkylation−C-Allylation Reaction of α-Imino Esters with Organoaluminums and Allyltributyltin

  摘要：

  On treatment of various alpha-imino esters with organoaluminum reagents and allyltributyltin in the presence of benzoyl peroxide, the tandem reaction proceeded to give the N-alkylation-C-allylation products in good yields. The tandem N-alkyation-C-cyanation also proceeded using silyl or aluminum cyanide to give the aminonitrile in good yield.

  DOI：

  10.1021/ja029639o

文献信息

• Conjugated imines and iminium salts as versatile acceptors of nucleophiles
  作者：Makoto Shimizu、Iwao Hachiya、Isao Mizota

  DOI：10.1039/b814930e

  日期：——

  development of synthetic methodologies where nucleophilic addition reactions to imino carbons are utilized in crucial steps. This article summarizes double nucleophilic addition reactions with alpha,beta-unsaturated aldimines, addition reactions using alkynyl imines, "umpoled" reactions of alpha-imino esters, and the use of iminium salts as reactive electrophiles.

  对涉及生物活性和功能材料的含氮分子的兴趣日益增长，刺激了合成方法的最新发展，在关键步骤中利用了对亚氨基碳的亲核加成反应。本文总结了与α，β-不饱和醛亚胺的双亲核加成反应，使用炔基亚胺的加成反应，α-亚氨基酯的“团聚”反应以及亚胺盐作为反应性亲电试剂的使用。
• An umpolung reaction of α-iminothioesters possessing a cyclopropyl group
  作者：Makoto Shimizu、Takayoshi Morimoto、Yusuke Yanagi、Isao Mizota、Yusong Zhu

  DOI：10.1039/d0ra01152e

  日期：——

  An umpolung N-alkylation reaction of α-cyclopropyl α-iminothioesters with diethylaluminum chloride or ethylmagnesium bromide affords the corresponding N-ethylated α-aminothioesters in good yields. Subsequent oxidation and reaction of the N-ethylated product with a thiolate or a chloride anion proceed effectively to give the ring-opened products in good yields. In contrast, relatively “hard” nucleophiles

  α-环丙基 α-亚氨基硫酯与二乙基氯化铝或乙基溴化镁的 umpolung N-烷基化反应以良好的收率提供相应的N-乙基化 α-氨基硫酯。N-乙基化产物与硫醇盐或氯阴离子的后续氧化和反应有效地进行，以良好的收率得到开环产物。相比之下，相对“硬”的亲核试剂不会产生开环产物，而是会产生亚胺碳的加成产物。
• Tandem N-Alkylation−C-Allylation Reaction of α-Imino Esters with Organoaluminums and Allyltributyltin
  作者：Yasuki Niwa、Makoto Shimizu

  DOI：10.1021/ja029639o

  日期：2003.4.1

  On treatment of various alpha-imino esters with organoaluminum reagents and allyltributyltin in the presence of benzoyl peroxide, the tandem reaction proceeded to give the N-alkylation-C-allylation products in good yields. The tandem N-alkyation-C-cyanation also proceeded using silyl or aluminum cyanide to give the aminonitrile in good yield.