(Z)-methyl 2-(6-iodohex-5-enamido)acetate | 849800-96-0

• 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)-methyl 2-(6-iodohex-5-enamido)acetate
• 英文别名: methyl 2-(6-iodohex-5Z-enamido)acetate；methyl 2-[[(Z)-6-iodohex-5-enoyl]amino]acetate
• CAS: 849800-96-0
• 化学式: C₉H₁₄INO₃
• 分子量: 311.12
• InChiKey: OTBZXXASMRPPMB-XQRVVYSFSA-N

物化性质

• 沸点：
  378.0±32.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  7
• 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：

  反-肉桂酰胺 、 (Z)-methyl 2-(6-iodohex-5-enamido)acetate 在 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以55%的产率得到methyl 2-(6-cinnamamidohex-5Z-enamido)acetate
  参考文献：
  名称：

  Synthesis of (+)-crocacin D and simplified bioactive analogues

  摘要：

  The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.008
• 作为产物：
  描述：

  methyl 2-(N-(tert-butoxycarbonyl)-5-oxopentanamido)acetate 在 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 (Z)-methyl 2-(6-iodohex-5-enamido)acetate
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k

文献信息

• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.
• Synthesis of (+)-crocacin D and simplified bioactive analogues
  作者：Adele E. Pasqua、Frank D. Ferrari、James J. Crawford、William G. Whittingham、Rodolfo Marquez

  DOI：10.1016/j.bmc.2015.01.008

  日期：2015.3

  The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported. (C) 2015 Elsevier Ltd. All rights reserved.