(Z)-2-Chloro-1-phenyl-1,3-butadiene | 160721-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-Chloro-1-phenyl-1,3-butadiene
• 英文别名: [(1Z)-2-chlorobuta-1,3-dienyl]benzene
• CAS: 160721-87-9
• 化学式: C₁₀H₉Cl
• 分子量: 164.634
• InChiKey: ZATDPPAGKWQMST-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  3-hydroxy-5,5-dimethyl-2-phenylcyclohex-2-en-1-one 、 (Z)-2-Chloro-1-phenyl-1,3-butadiene 在 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以67%的产率得到2'-[(Z)-1-chloro-2-phenylethenyl]-4,4-dimethyl-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-2,6-dione
  参考文献：
  名称：

  Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C–H functionalization

  摘要：

  用钯催化的氧化性环化反应，将非活化或弱活化的1,3-二烯烃与2-芳基环状1,3-二羰基化合物发生环化反应。

  DOI：

  10.1039/c4cc09496d
• 作为产物：
  描述：

  (E)-trimethyl(3-phenylallyl)silane 以33%的产率得到
  参考文献：
  名称：

  Mitani Michiharu, Kobayashi Yosinori, Koyama Kikuhiko, J. Chem. Soc. Perkin Trans. 1, (1995) N 6, S 653-655

  摘要：

  DOI：

文献信息

• Electronic and Conformational Effects in the Photochemistry of .alpha.-Alkenyl-Substituted Vinyl Halides
  作者：Erik S. Krijnen、Han Zuilhof、Gerrit Lodder

  DOI：10.1021/jo00105a035

  日期：1994.12

  The photochemical reactions in methanol of the vinylic halides 2-halo-1-phenyl-1,3-butadienes 1-3Z-X (beta-halo-beta-alkenylstyrenes) and 1-halo-1,2-diphenylethenes 4Z-X (alpha-halostilbenes), with X = Cl or Br, have been studied quantitatively. E/Z isomerization, dehydrohalogenation, nucleophilic substitution, a [1,3]-halogen shift, a [1,3]-hydrogen shift, and oxidation are observed as the primary reactions. No reductive dehalogenation products are formed. The efficiencies of product formation are dependent on the halogen used, the electron-donating capacity of the a-substituent, the ground state conformation of the starting material, and the wavelength of excitation. Apart from the photoinduced E/Z isomerization and the oxidation reaction typical for alkenes, product formation occurs exclusively via vinyl-cationic intermediates, which are formed upon photolytic cleavage of the carbon-halogen bond. These ionic species, or part of them, are present as vinyl cation/halide anion-pairs.
• Mitani, Michiharu; Kobayashi, Yoshinori; Koyama, Kikuhiko, Journal of the Chemical Society. Perkin transactions I, 1995, # 6, p. 653 - 656
  作者：Mitani, Michiharu、Kobayashi, Yoshinori、Koyama, Kikuhiko

  DOI：——

  日期：——
• Chloroprene as a Source of Fine Chemicals:  Palladium-Catalyzed Synthesis of Terminal Allenes
  作者：Masamichi Ogasawara、Hisashi Ikeda、Takashi Nagano、Tamio Hayashi

  DOI：10.1021/ol016320k

  日期：2001.8.9

  [GRAPHICS]Several functionalized terminal allenes were prepared in moderate to excellent yield by a palladium-catalyzed reaction of chloroprene (2-chloro-1,3-butadiene) with soft nucleophiles.
• Mitani Michiharu, Kobayashi Yosinori, Koyama Kikuhiko, J. Chem. Soc. Perkin Trans. 1, (1995) N 6, S 653-655
  作者：Mitani Michiharu, Kobayashi Yosinori, Koyama Kikuhiko

  DOI：——

  日期：——
• SEYFERTH D.; MAMMARELLE R. E., J. ORGANOMETAL. CHEM., 1978, 156, NO 2, 279-297
  作者：SEYFERTH D.、 MAMMARELLE R. E.

  DOI：——

  日期：——