(E)-6-chloro-2-methylhex-5-en-3-yn-2-ol | 464923-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-6-chloro-2-methylhex-5-en-3-yn-2-ol
• CAS: 464923-03-3
• 化学式: C₇H₉ClO
• 分子量: 144.601
• InChiKey: XVPAFYVYSCNZMW-GQCTYLIASA-N

物化性质

• 沸点：
  190.6±25.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (E)-6-chloro-2-methylhex-5-en-3-yn-2-ol 在 copper(l) iodide 、 四(三苯基膦)钯 哌啶 作用下， 生成 (E)-7-Methyl-5-((E)-non-1-en-3-ynyl)-oct-5-en-3-yne-1,7-diol
  参考文献：
  名称：

  The first and convenient synthesis of acyclic dienediynes related to neocarzinostatin chromophore

  摘要：

  A stereocontrolled and flexible synthetic approach to acyclic (E,E) and (Z,E)-dienediynes, related to the neocarzinostatin chromophore 5, from readily available stannylated chlorodienes 1 and dienynes 2 is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00693-5
• 作为产物：
  描述：

  反-1,2-二氯乙烯 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以65%的产率得到(E)-6-chloro-2-methylhex-5-en-3-yn-2-ol
  参考文献：
  名称：

  Regiocontrol of the Palladium-Catalyzed Tin Hydride Addition to Z-Enynols:  Remarkable Z-Directing Effects

  摘要：

  [GRAPHICS]Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the double bond ( Z- or syn-directing effect) rather than the nature of its substituents. Exclusively alpha-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.

  DOI：

  10.1021/jo0701435

文献信息

• Synthesis of substituted quinolines by iron-catalyzed coupling reactions between chloroenynes and Grignard reagents
  作者：Matar Seck、Xavier Franck、Reynald Hocquemiller、Bruno Figadère、Jean-François Peyrat、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.tetlet.2004.01.019

  日期：2004.2

  letter reports the preparation of quinolines, substituted at the 2- or 3-position by a 4-substituted but-3-en-1-yne group, by the environmentally friendly iron(III)-catalyzed coupling reaction of Grignard reagents with 1-chloro-4-(2-quinolyl)but-1-en-3-yne. The extension and the scope of this non-toxic and chemoselective procedure to various functionalized unsaturated vinyl chlorides are described.

  这封信报道了由环保的铁（III）催化的格氏试剂与1的环境友好的铁（III）偶联反应制备2-位或3-位被4-取代的丁-3-烯-1-炔基取代的喹啉。 -氯-4-（2-喹啉基）但是-1-烯-3-炔 描述了该无毒和化学选择性方法对各种官能化的不饱和氯乙烯的扩展和范围。
• Versatile palladium(II)-catalyzed Negishi coupling reactions with functionalized conjugated alkenyl chlorides
  作者：Jean-François Peyrat、Emmanuel Thomas、Nathalie L'Hermite、Mouâd Alami、Jean-Daniel Brion

  DOI：10.1016/s0040-4039(03)01627-7

  日期：2003.8

  Under palladium catalysis, we found that organozincate reagents, generated in situ, by reaction of Grignard compounds with less than molar amounts of zinc chloride, in the presence of conjugated alkenyl chlorides, give rapidly and cleanly the corresponding coupling product in high yields. In this way, aryl as well as primary and secondary alkyl substituents have been introduced successfully. The selectivity of the reaction allows to prepare various functionalized conjugated enynes and dienes from chloroenyne and chlorodiene derivatives bearing a functional group. (C) 2003 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of (E)-chloroenynes or (E,E)-chlorodienes starting from a stereoisomeric mixture of 1,2-dichloroethylenes
  作者：Mouâd Alami、Jean-François Peyrat、Jean-Daniel Brion

  DOI：10.1016/s0040-4039(02)00412-4

  日期：2002.4

  Under palladium or nickel catalysis. a stereomeric mixture 1:1 of (Z) and (E)-1,2-dichloroethylene readily reacts with 1-alkynes. vinyl alanes or vinyl boranes to afford selectively the corresponding (E)-coupling product in good to excellent isolated yields. The selectivity of this coupling reaction is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Regiocontrol of the Palladium-Catalyzed Tin Hydride Addition to <i>Z</i>-Enynols:  Remarkable <i>Z</i>-Directing Effects
  作者：Abdallah Hamze、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1021/jo0701435

  日期：2007.5.1

  [GRAPHICS]Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the double bond ( Z- or syn-directing effect) rather than the nature of its substituents. Exclusively alpha-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.
• The first and convenient synthesis of acyclic dienediynes related to neocarzinostatin chromophore
  作者：Murielle Bujard、Fabiola Ferri、Mouaˆd Alami

  DOI：10.1016/s0040-4039(98)00693-5

  日期：1998.6

  A stereocontrolled and flexible synthetic approach to acyclic (E,E) and (Z,E)-dienediynes, related to the neocarzinostatin chromophore 5, from readily available stannylated chlorodienes 1 and dienynes 2 is described. (C) 1998 Elsevier Science Ltd. All rights reserved.