(E)-N,N-Diisopropyl-3-(4-methoxyphenyl)-2-methylpropenamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N,N-Diisopropyl-3-(4-methoxyphenyl)-2-methylpropenamide
• 英文别名: (E)-3-(4-methoxyphenyl)-2-methyl-N,N-di(propan-2-yl)prop-2-enamide
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: JFEBMXCEOSBFSS-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 (E)-N,N-Diisopropyl-3-(4-methoxyphenyl)-2-methylpropenamide 在 三氢化钐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到(1S*,2R*)-N,N-diisopropyl-1-methyl-2-(4-methoxyphenyl)cyclopropanecarboxamide
  参考文献：
  名称：

  Complete Stereospecific Cyclopropanation of α,β-Unsaturated Amides Promoted by Sm/CH2I2 We acknowledge financial support from II Plan Regional de Investigación del Principado de Asturias (PB-EXP01-11) and Ministerio de Ciencia y Tecnología (BQU2001-3807). We thank Dr. Francisco J. González for valuable discussions and Robin Walker for revising the English manuscript. J.M.C. thanks Carmen Fernández-Flórez for her time. H.R.S. thanks Principado de Asturias for a predoctoral fellowship.

  摘要：

  DOI：

  10.1002/1521-3773(20020603)41:11<1917::aid-anie1917>3.0.co;2-1
• 作为产物：
  描述：

  2-Chloro-N,N-diisopropyl-3-hydroxy-2-methyl-3-(4-methoxyphenyl)propanamide 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (Z)-N,N-Diisopropyl-2-methyl-3-phenylpropenamide 、 (E)-N,N-Diisopropyl-3-(4-methoxyphenyl)-2-methylpropenamide
  参考文献：
  名称：

  Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide

  摘要：

  Stereoselective beta -elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta -unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds a are easily prepared by reaction of the corresponding lithium enolates of alpha -chloroamides with aldehydes or ketones at -78 degreesC. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta -elimination reaction is also discussed.

  DOI：

  10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f

文献信息

• Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide
  作者：José M. Concellón、Juan A. Pérez-Andrés、Humberto Rodríguez-Solla

  DOI：10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f

  日期：2001.7.16

  Stereoselective beta -elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta -unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds a are easily prepared by reaction of the corresponding lithium enolates of alpha -chloroamides with aldehydes or ketones at -78 degreesC. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta -elimination reaction is also discussed.
• Complete Stereospecific Cyclopropanation of α,β-Unsaturated Amides Promoted by Sm/CH2I2 We acknowledge financial support from II Plan Regional de Investigación del Principado de Asturias (PB-EXP01-11) and Ministerio de Ciencia y Tecnología (BQU2001-3807). We thank Dr. Francisco J. González for valuable discussions and Robin Walker for revising the English manuscript. J.M.C. thanks Carmen Fernández-Flórez for her time. H.R.S. thanks Principado de Asturias for a predoctoral fellowship.
  作者：José M. Concellón、Humberto Rodríguez-Solla、Cecilia Gómez

  DOI：10.1002/1521-3773(20020603)41:11<1917::aid-anie1917>3.0.co;2-1

  日期：2002.6.3