Z-dec-2-enoic acid methoxy-methyl-amide

• 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: Z-dec-2-enoic acid methoxy-methyl-amide
• 英文别名: (Z)-N-methoxy-N-methyldec-2-enamide
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: ZUNPUDZDECCWPL-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  正辛醛 、 [(methoxy-methyl-carbamoyl)-methyl]-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester 在 18-冠醚-6 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到Z-dec-2-enoic acid methoxy-methyl-amide
  参考文献：
  名称：

  A New Bis(2,2,2-trifluoroethyl)phosphonate for the Synthesis of Z-Unsaturated N-Methoxy-N-methylamides

  摘要：

  The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.

  DOI：

  10.1021/jo025816s

文献信息

• Preparations of Z-α,β-Unsaturated Amides by Using Horner-Wadsworth-Emmons Reagents, (Diphenylphosphono)acetamides
  作者：Kaori Ando

  DOI：10.1055/s-2001-16072

  日期：——

  New Horner-Wadsworth-Emmons reagents, (diphenylphosphono)acetamides 2 react with a variety of aldehydes to give the corresponding Z-α,β-unsaturated amides stereoselectively (up to Z : E = 98 : 2).

  新型的Horner-Wadsworth-Emmons试剂，即(二苯基膦酰)乙酰胺2，可以与多种醛类反应，选择性地得到相应的Z-α,β-不饱和酰胺（Z : E 的比例最高可达98 : 2）。
• Bis(2-t-butylphenyl)phosphonoacetamides for the highly cis-selective synthesis of α,β-unsaturated amides
  作者：Kaori Ando、Shigeo Nagaya、Yuko Tarumi

  DOI：10.1016/j.tetlet.2009.07.130

  日期：2009.10

  New Horner-Wadsworth-Emmons reagents, (o-t-BuPhO)(2)P(O)CH2CONMe(OMe) and (o-t-BuPhO)(2)-P(O)CH2CON(CH2CH2) O-2 were prepared via the Arbuzov reaction in good yields. The HWE reaction of these reagents with a variety of aldehydes gave cis-alpha,beta-unsaturated amides with high selectivity in almost quantitative yields. (C) 2009 Published by Elsevier Ltd.
• A New Bis(2,2,2-trifluoroethyl)phosphonate for the Synthesis of <i>Z</i>-Unsaturated <i>N</i>-Methoxy-<i>N</i>-methylamides
  作者：Samuel Fortin、Félix Dupont、Pierre Deslongchamps

  DOI：10.1021/jo025816s

  日期：2002.7.1

  The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.