(E)-4-iodobut-3-enoic acid | 190203-25-9

• 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: (E)-4-iodobut-3-enoic acid
• 英文别名: (E)-4-iodobut-3-en-1-oic acid
• CAS: 190203-25-9
• 化学式: C₄H₅IO₂
• 分子量: 211.987
• InChiKey: GIWJCGYGNIHOKS-HNQUOIGGSA-N

物化性质

• 熔点：
  56-58 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  277.0±23.0 °C(Predicted)
• 密度：
  2.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-iodobut-3-enoic acid 、 zinc methyl bromide 在 双(乙腈)氯化钯(II) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以90%的产率得到3-戊烯酸
  参考文献：
  名称：

  Stereoselective access to functionalized β-γ unsaturated acids

  摘要：

  Stereoselective synthesis of vinylstannanes bearing a carboxylic acid function was achieved from beta-gamma alkynoic acids via hydrostannation, stannylcupration or silastannation reactions. Regioselectivity is highly dependent on the nature of the stannylanions used and on protection of the carboxylic acid function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00616-1
• 作为产物：
  描述：

  (E)-4-iodo-3-buten-1-ol 以90%的产率得到(E)-4-iodobut-3-enoic acid
  参考文献：
  名称：

  Transannular Diels-Alder approach to the synthesis of momilactone A

  摘要：

  The application of the transannular Diels-Alder strategy on macrocyclic trienes having the trans-trans-cis olefin geometry led to trans-syn-trans tricycles which are advanced intermediates for the synthesis of natural products like Momilactone A. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00669-3

文献信息

• Stannylmetallation of acetylenic acids: a stereoselective access to functionalized α, β- and β, γ-unsaturated acids
  作者：Je´rome Thibonnet、Vale´rie Launay、Mohamed Abarbri、Alain Ducheˆne、Jean-Luc Parrain

  DOI：10.1016/s0040-4039(98)00753-9

  日期：1998.6

  The stereoselective synthesis of vinylstannanes bearing car☐ylic acid function was achieved from acetylenic acids via stannylcupration reaction. In homoallylic series, regioselectivities are highly dependant on the nature of stannylanionids and on the protection of the car☐ylic acid function.

  通过乙炔酸经苯乙烯基转移反应实现了具有汽车☐丙烯酸功能的乙烯基锡烷的立体选择性合成。在同烯丙基系列中，区域选择性高度依赖于锡兰尼类化合物的性质以及对汽车☐酸功能的保护。
• Transannular Diels-Alder approach to the synthesis of momilactone A
  作者：Julie Germain、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(99)00669-3

  日期：1999.5

  The application of the transannular Diels-Alder strategy on macrocyclic trienes having the trans-trans-cis olefin geometry led to trans-syn-trans tricycles which are advanced intermediates for the synthesis of natural products like Momilactone A. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereoselective access to functionalized β-γ unsaturated acids
  作者：Jérôme Thibonnet、Mohamed Abarbri、Jean-Luc Parrain、Alain Duchêne

  DOI：10.1016/s0040-4020(03)00616-1

  日期：2003.6

  Stereoselective synthesis of vinylstannanes bearing a carboxylic acid function was achieved from beta-gamma alkynoic acids via hydrostannation, stannylcupration or silastannation reactions. Regioselectivity is highly dependent on the nature of the stannylanions used and on protection of the carboxylic acid function. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of (±)-Momilactone A
  作者：Julie Germain、Pierre Deslongchamps

  DOI：10.1021/jo025873l

  日期：2002.7.1

  The first total synthesis of (+/-)-momilactone A was accomplished using a highly diastereoselective transannular Diels-Alder reaction on a trans-trans-cis macrocyclic triene.