ethyl N-acetyl-D,L-4-iodoallylglycinate | 144332-86-5

• 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 N-acetyl-D,L-4-iodoallylglycinate
• 英文别名: ethyl N-acetyl-4-iodoallylglycinate；Ethyl 2-acetamido-4-iodopent-4-enoate
• CAS: 144332-86-5
• 化学式: C₉H₁₄INO₃
• 分子量: 311.12
• InChiKey: JSIMWLNJMQBRRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-庚炔 、 ethyl N-acetyl-D,L-4-iodoallylglycinate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到ethyl 2-acetamido-4-methylene-undec-5-ynoate
  参考文献：
  名称：

  Elaboration of the side chain of α-amino acids containing a vinyl iodide by palladium-catalysed coupling

  摘要：

  The palladium-catalysed coupling of a gamma-iodoallylglycine derivative and an E-delta-iodoallylglycine derivative with various organic nucleophiles is described.

  DOI：

  10.1016/s0040-4020(01)86978-7
• 作为产物：
  描述：

  ethyl N-acetyl-D,L-4-(tri-n-butylstannyl)allylglycinate 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以64%的产率得到ethyl N-acetyl-D,L-4-iodoallylglycinate
  参考文献：
  名称：

  Synthesis and transformations of trialkylstannyl-substituted allylglycine derivatives.

  摘要：

  The three racemic vinylstannyl allylglycine derivatives (1, E-2, Z-2) were prepared by a variety of hydrostannation reactions. These vinylstannanes were converted to the corresponding vinyl iodides (7, E-8, Z-8) by electrophilic iodination and to symmetrical 1,3-dienes (5, 6) by copper catalysed coupling. A cis-bis(trimethylstannyl)allylglycine derivative (cis-4) was also prepared by palladium catalysed addition of hexamethylditin.

  DOI：

  10.1016/s0040-4039(00)61336-9

文献信息

• Synthesis of α,β-unsaturated lactams by palladium-catalysed intramolecular carbonylative coupling
  作者：Geoffrey T. Crisp、Adam G. Meyer

  DOI：10.1016/0040-4020(95)00219-x

  日期：1995.5

  Amino vinyl triflates have been shown to undergo an intramolecular, carbonylative coupling in the presence of a palladium catalyst to afford α,β-unsaturated lactams.

  已显示氨基乙烯基三氟甲磺酸酯在钯催化剂的存在下进行分子内的羰基化偶联，以提供α，β-不饱和内酰胺。
• Synthesis and transformations of trialkylstannyl-substituted allylglycine derivatives.
  作者：Geoffrey T. Crisp、Peter T. Glink

  DOI：10.1016/s0040-4039(00)61336-9

  日期：1992.8

  The three racemic vinylstannyl allylglycine derivatives (1, E-2, Z-2) were prepared by a variety of hydrostannation reactions. These vinylstannanes were converted to the corresponding vinyl iodides (7, E-8, Z-8) by electrophilic iodination and to symmetrical 1,3-dienes (5, 6) by copper catalysed coupling. A cis-bis(trimethylstannyl)allylglycine derivative (cis-4) was also prepared by palladium catalysed addition of hexamethylditin.
• Elaboration of the side chain of α-amino acids containing a vinyl iodide by palladium-catalysed coupling
  作者：Geoffrey T. Crisp、Peter T. Glink

  DOI：10.1016/s0040-4020(01)86978-7

  日期：1994.2

  The palladium-catalysed coupling of a gamma-iodoallylglycine derivative and an E-delta-iodoallylglycine derivative with various organic nucleophiles is described.