(E)-N,N-二乙基-3-庚烯酰胺 | 103896-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-N,N-二乙基-3-庚烯酰胺
• 英文名称: (E)-N,N-diethyl-3-heptenamide
• 英文别名: (3E)-N,N-diethyl-3-heptenamide；(E)-N,N-diethylhept-3-enamide
• CAS: 103896-63-5
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: XLFZDVUBYUXAGZ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-[(2E)-hex-2-enyl]-N,N-diethylamine 以83%的产率得到
  参考文献：
  名称：

  Murahashi Shun-Ichi, Imada Yasushi, Nishimura Koichi, Tetrahedron, 50 (1994) N 2, S 453-464

  摘要：

  DOI：

文献信息

• RHODIUM-CATALYZED AZACARBONYLATION OF ALLYL PHOSPHATES. THE PREPARATION OF β,γ-UNSATURATED AMIDES FROM ALLYL ALCOHOLS
  作者：Shun-Ichi Murahashi、Yasushi Imada

  DOI：10.1246/cl.1985.1477

  日期：1985.10.5

  Allyl phosphates undergo a smooth azacarbonylation reaction with amines to afford β,γ-unsaturated amides at 50 °C under CO atmosphere (20 atm) in the presence of Rh6(CO)16 catalyst and Bu4NCl co-catalyst.

  在 Rh6(CO)16 催化剂和 Bu4NCl 助催化剂的作用下，烯丙基磷酸盐与胺在 50 °C 的 CO 大气（20 个大气压）中顺利发生偶氮羰基化反应，生成 β,γ-不饱和酰胺。
• Aza- and oxacarbonylations of allyl phosphates catalyzed by rhodium carbonyl cluster. Selective synthesis of β, γ-unsaturated amides, esters, and acids
  作者：Yasushi Imada、Ou Shibata、Shun-Ichi Murahashi

  DOI：10.1016/0022-328x(93)83025-q

  日期：1993.6

  Rhodium-catalyzed carbonylation of allyl phosphates under CO (20 atm) at 50°C proceeds very efficiently in the presence of amines, alcohols, and water to give the corresponding β,γ-unsaturated amides, esters, and acids, respectively. These carbonylations occur with high regioselectivity at the less substituted carbon of allyl unit to give linear β,γ-unsaturated acid derivatives.

  在胺，醇和水的存在下，在50°C的CO（20 atm）下铑的烯丙基磷酸酯的羰基催化羰基化反应非常有效，分别得到相应的β，γ-不饱和酰胺，酯和酸。这些羰基化在烯丙基单元的较少取代的碳上以较高的区域选择性发生，从而得到线性的β，γ-不饱和酸衍生物。
• Palladium-catalyzed Carbonylation of Allylamines. Synthesis of β,γ-unsaturated amides by one-carbon homologation of Allylamines
  作者：Shun-Ichi Murahashi、Yasushi Imada、Koichi Nishimura

  DOI：10.1016/s0040-4020(01)80767-5

  日期：1994.1

  Palladium-catalyzed carbonylation of allylamines under CO (50atm) at 110°C proceeds highly efficiently to give the corresponding β,γ-unsaturated amides. The carbonylation occurs at the less substituted carbon of allyl units to give linear amides with high regioselectivity. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium (0) species to allylamines

  在110°C的CO（50atm）下钯烯丙基胺的羰基催化羰基化反应非常高效，得到相应的β，γ-不饱和酰胺。羰基化发生在烯丙基单元的较少取代的碳上，得到具有高区域选择性的线性酰胺。可以通过假设以下机理来使反应合理化：该机理涉及将钯（0）物种氧化添加到烯丙胺中以生成π-烯丙基钯络合物，插入一氧化碳以生成酰基戊烯物种和酰胺化。
• (E)-β,γ-unsaturated amides from (E)-9-alkenyl-9-borabicyclo[3.3.1]nonane and N,N-dialkyl(dimethylsulfuranylidene)acetamide
  作者：Min-Zhi Deng、Nan-Sheng Li、Yao-Zeng Huang

  DOI：10.1039/c39930000065

  日期：——

  A facile route for the stereocontrolled synthesis of (E)-β,γ-unsaturated amides by the reaction of stereodefined 9-alkenyl-9-borabicyclo[3.3.1]nonane with N,N-dialkyl(dimethylsulfuranylidene)acetamide is described.

  本研究描述了通过立体定义的 9-烯基-9-硼杂双环[3.3.1]壬烷与 N,N-二烷基（二甲基亚硫酰）乙酰胺反应，立体控制合成 (E)-δ²,δ³-不饱和酰胺的简便路线。
• Palladium-catalysed carbonylation of allylamines
  作者：Shun-Ichi Murahashi、Yasushi Imada、Koichi Nishimura

  DOI：10.1039/c39880001578

  日期：——

  Carbonylation of allylamines proceeds smoothly in the presence of a palladium–phosphine catalyst to give β,γ-unsaturated amides in good yields.

  在钯-膦催化剂的存在下，烯丙胺的羰基化反应平稳进行，从而以高收率得到β，γ-不饱和酰胺。