(Z)-2-(2-chlorovinyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-(2-chlorovinyl)naphthalene
• 英文别名: 2-[(Z)-2-chlorovinyl]naphthalene；2-[(Z)-2-chloroethenyl]naphthalene
• 化学式: C₁₂H₉Cl
• 分子量: 188.656
• InChiKey: QXRPPXZDOLFOLG-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  反-1,2-二氯乙烯 、 2-萘硼酸 在 potassium phosphate 、 [Rh(OH)(cod)]2 、 1,4-双(二苯基膦)丁烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以88%的产率得到
  参考文献：
  名称：

  铑催化的烯基卤化物与芳基硼化合物的交叉偶联

  摘要：

  AbstractThe rhodium(I)‐catalyzed reaction between arylboronic esters and excess 1,2‐dichloroethene selectively afforded (2‐chlorovinyl)arenes. Double arylation yielding 1,2‐diarylethenes was observed when 1,2‐dibromoethene was reacted with 2.5 equivalents of arylboronic acid.magnified image

  DOI：

  10.1002/adsc.201300482

文献信息

• Chromium-catalyzed olefination of arylaldehydes with haloforms assisted by 2,3,5,6-tetramethyl-<i>N</i>,<i>N</i>′-bis(trimethylsilyl)-1,4-dihydropyrazine
  作者：Kohei Nishi、Hayato Tsurugi、Kazushi Mashima

  DOI：10.1039/d2cc06104j

  日期：——

  Chromium-catalyzed olefination of arylaldehydes with haloforms was achieved using 2,3,5,6-tetramethyl-N,N′-bis(trimethylsilyl)-1,4-dihydropyrazine (1a) as an organic reducing agent, giving β-halostyrene derivatives in a trans-selective manner. The reaction required no metal powders, such as zinc and manganese, as reductants, thereby minimizing metal-based reaction waste.

  以2,3,5,6-四甲基-N , N'-双(三甲基甲硅烷基)-1,4-二氢吡嗪( 1a )为有机还原剂,铬催化卤代芳醛烯化,得到β-卤代苯乙烯衍生物以反式选择的方式。该反应不需要锌和锰等金属粉末作为还原剂，从而最大限度地减少了金属基反应废物。
• Stereoselective Synthesis of <i>Z</i> Alkenyl Halides via Julia Olefination
  作者：Marie-Eve Lebrun、Paul Le Marquand、Carl Berthelette

  DOI：10.1021/jo052370h

  日期：2006.3.1

  Julia olefination between alpha-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereo selectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the Z solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.
• Rhodium-Catalyzed Cross-Coupling of Alkenyl Halides with Arylboron Compounds
  作者：Takanori Matsuda、Kentaro Suzuki、Norio Miura

  DOI：10.1002/adsc.201300482

  日期：2013.11.25

  AbstractThe rhodium(I)‐catalyzed reaction between arylboronic esters and excess 1,2‐dichloroethene selectively afforded (2‐chlorovinyl)arenes. Double arylation yielding 1,2‐diarylethenes was observed when 1,2‐dibromoethene was reacted with 2.5 equivalents of arylboronic acid.magnified image