ethyl (E,E)-5-iodo-3-methylpenta-2,4-dienoate | 144950-83-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E,E)-5-iodo-3-methylpenta-2,4-dienoate
• 英文别名: ethyl (2E,4E)-5-iodo-3-methylpenta-2,4-dienoate
• CAS: 144950-83-4
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: IRENBIOKVOANHZ-YTXTXJHMSA-N

物化性质

• 沸点：
  264.5±23.0 °C(Predicted)
• 密度：
  1.565±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E,E)-5-iodo-3-methylpenta-2,4-dienoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到(2E,4E)-5-iodo-3-methylpenta-2,4-dien-1-ol
  参考文献：
  名称：

  The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids

  摘要：

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.

  DOI：

  10.1016/0040-4020(94)01108-c
• 作为产物：
  描述：

  碘仿 、 3-甲酰基-2-丁烯酸乙酯 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以50%的产率得到ethyl (E,E)-5-iodo-3-methylpenta-2,4-dienoate
  参考文献：
  名称：

  General Synthesis of Retinoids and Arotinoids via Palladium-Catalyzed Cross-Coupling of Boronic Acids with Electrophiles

  摘要：

  本文介绍了一种制备类视黄醇和阿洛视黄醇（包括杂环类似物）的新方法，该方法基于铊促进的钯催化下硼酸与多种亲电试剂的交叉偶联合成反应（Suzuki反应）。

  DOI：

  10.1055/s-1995-3905

文献信息

• Stereospecific synthesis of 9-demethylretinoids via palladium-catalyzed vinylboronic acid-vinyl iodide cross coupling
  作者：Angel R. de Lera、Alicia Torrado、Beatriz Iglesias、Susana López

  DOI：10.1016/s0040-4039(00)60044-8

  日期：1992.10

  A stereospecific synthesis of 9-demethylretinoids with either trans or 11-cis geometries, based on the thallium-accelerated palladium-catalyzed cross-coupling reactions of an (E)-1-alkenylboronic acid and (E) or (Z)-alkenyl iodides, is described.
• General Synthesis of Retinoids and Arotinoids via Palladium-Catalyzed Cross-Coupling of Boronic Acids with Electrophiles
  作者：Alicia Torrado、Susana López、Rosana Alvarez、Angel R. de Lera

  DOI：10.1055/s-1995-3905

  日期：1995.3

  A novel approach to the synthesis of retinoids and arotinoids (including heterocyclic analogs) is described which is based on the thallium-accelerated palladium-catalyzed cross-coupling of boronic acids with a variety of electrophiles (the Suzuki reaction).

  本文介绍了一种制备类视黄醇和阿洛视黄醇（包括杂环类似物）的新方法，该方法基于铊促进的钯催化下硼酸与多种亲电试剂的交叉偶联合成反应（Suzuki反应）。
• The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids
  作者：Alicia Torrado、Beatriz Iglesias、Susana López、Angel R. de Lera

  DOI：10.1016/0040-4020(94)01108-c

  日期：1995.2

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.