(2E,4E)-5-iodo-3-methylpenta-2,4-dien-1-ol | 108204-11-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (2E,4E)-5-iodo-3-methylpenta-2,4-dien-1-ol
• 英文别名: (E,E)-5-iodo-3-methylpenta-2,4-dien-1-ol
• CAS: 108204-11-1
• 化学式: C₆H₉IO
• 分子量: 224.041
• InChiKey: JKVJZHMYWQBFAC-PIXFVPMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-iodo-3-methylpenta-2,4-dien-1-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 维生素A
  参考文献：
  名称：

  Highly selective synthesis of vitamin A and its derivatives. Critical comparison of some known palladium-catalyzed alkenyl-alkenyl coupling reactions

  摘要：

  Vitamin A has been synthesized cleanly and selectively with essentially complete control of stereo- and regiochemistry in four linear and six overall steps from beta-ionone and (E)-3-methyl-2-penten-4-yn-1-ol via Pd-catalyzed cross coupling of an alkenylzinc with an alkenyl iodide; the use of other metals, such as Al, Zr, Mg, B, Cu, and Sn, being inferior to that of Zn.

  DOI：

  10.1016/s0040-4039(00)93574-3
• 作为产物：
  描述：

  3-甲酰基-2-丁烯酸乙酯 在 chromium dichloride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 (2E,4E)-5-iodo-3-methylpenta-2,4-dien-1-ol
  参考文献：
  名称：

  Stereospecific synthesis of 9-demethylretinoids via palladium-catalyzed vinylboronic acid-vinyl iodide cross coupling

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60044-8

文献信息

• A comprehensive survey of stille-type Csp2-Csp2 single bond forming processes in the synthesis of retinoic acid and analogs
  作者：Beatriz Domínguez、Beatriz Iglesias、Angel R. de Lera

  DOI：10.1016/s0040-4020(99)00962-x

  日期：1999.12

  coupling for the formation of the side-chain single bonds. On employing the experimental catalytic conditions developed by Farina [Pd2(dba)3, AsPh3, NMP] we have modified the electronic and steric requirement of the coupling parters, alkenyl stannanes and electrophiles (alkenyl iodides and triflates). The comprehensive survey afforded appropriately matched components for every bond formation considered.

  已经使用Stille偶联详尽地研究了类维生素A骨架的合成以形成侧链单键。使用Farina [Pd 2（dba）3，AsPh 3，NMP]，我们已经修改了偶联伙伴，烯基锡烷和亲电子试剂（烯基碘化物和三氟甲磺酸酯）的电子和空间要求。全面的调查为所考虑的每种债券形成提供了适当匹配的组成部分。此外，通过比较具有不同空间位阻程度的不同偶联配偶体的反应性，证实了斯蒂勒偶联对空间效应的敏感性。除了为类维生素A合成提供了多种构建基块之外，该研究还强调了一些趋势，这些趋势对于将Stille反应应用于未取代共轭多烯的合成可能有用。
• Hiyama Cross-Coupling Reaction in the Stereospecific Synthesis of Retinoids
  作者：Javier Montenegro、Julián Bergueiro、Carlos Saá、Susana López

  DOI：10.1021/ol101513n

  日期：2010.8.20

  Page 144. Supporting Information has been added. This information was omitted in error when the paper was published. General methods, experimental procedures, tables of spectroscopic data, and NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org. This article has not yet been cited by other publications. General methods, experimental procedures, tables of spectroscopic

  页面144。已添加支持信息。论文发表时错误地省略了此信息。一般方法，实验程序，光谱数据表和NMR光谱。可通过Internet（http://pubs.acs.org）免费获得此材料。本文尚未被其他出版物引用。一般方法，实验程序，光谱数据表和NMR光谱。可通过Internet（http://pubs.acs.org）免费获得此材料。
• An efficient method in stannylcupration of a methyl substituted enyne or alkyne by kinetic control using methanol
  作者：Jean-François Betzer、Janick Ardisson、Jean-Yves Lallemand、Ange Pancrazi

  DOI：10.1016/s0040-4039(97)00361-4

  日期：1997.3

  Stannylcupration of enyne 5 was performed with the homostannylcuprate (Bu3Sn)2CuCNLi2 to deliver in a stereoselective way the distal dienylstannane 7 in 77% yield. This reaction was reproducible only when methanol was added to the cuprate solution. In comparison, hydroboration or hydrozirconation reactions failed in this case to produce the corresponding boron or zirconium derivative.

  用高锡锡酸铜（Bu 3 Sn）2 CuCNLi 2进行烯炔5的斯坦化作用，以立体选择的方式输送远端二烯基锡烷7，产率为77％。仅当将甲醇添加到铜酸盐溶液中时，该反应才可重现。相比之下，加氢硼化或加氢锆化反应在这种情况下不能产生相应的硼或锆衍生物。
• 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.
• Highly selective synthesis of vitamin A and its derivatives. Critical comparison of some known palladium-catalyzed alkenyl-alkenyl coupling reactions
  作者：Ei-ichi Negishi、Zbyslaw Owczarczyk

  DOI：10.1016/s0040-4039(00)93574-3

  日期：1991.11

  Vitamin A has been synthesized cleanly and selectively with essentially complete control of stereo- and regiochemistry in four linear and six overall steps from beta-ionone and (E)-3-methyl-2-penten-4-yn-1-ol via Pd-catalyzed cross coupling of an alkenylzinc with an alkenyl iodide; the use of other metals, such as Al, Zr, Mg, B, Cu, and Sn, being inferior to that of Zn.