(Z)-4-Chloro-4-octene | 7321-48-4

• 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: (Z)-4-Chloro-4-octene
• 英文别名: Z-4-chloro-4-octene；4-chloro-4-octene；(Z)-4-chloro-oct-4-ene；4-chloro-oct-4t-ene；4-chloro-oct-4-ene；4-Chlor-oct-4t-en；4-Octene, 4-chloro-, (Z)-；(Z)-4-chlorooct-4-ene
• CAS: 7321-48-4
• 化学式: C₈H₁₅Cl
• 分子量: 146.66
• InChiKey: YOZURJHSPCKCEV-FPLPWBNLSA-N

物化性质

• 沸点：
  190°C (estimate)
• 密度：
  0.9162 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (Z)-4-Chloro-4-octene 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 以75%的产率得到5-癸炔
  参考文献：
  名称：

  Mkrtchyan, A. M.; Gasparyan, S. M.; Sarkisyan, V. Yu., Journal of applied chemistry of the USSR, 1989, vol. 62, p. 1313 - 1315

  摘要：

  DOI：
• 作为产物：
  描述：

  顺-4-辛烯 在 potassium tert-butylate 、 氯 作用下， 以 氯仿 、 苯 为溶剂， 生成 (Z)-4-Chloro-4-octene
  参考文献：
  名称：

  金属结合现象：醇化物聚集为消除反应的直接参与者

  摘要：

  在低极性的溶剂既不是单分子，也不是解离alcoholal物种效应脱卤化氢的VIC -dihaloalkanes和VIC -dihalocycloalkanes而是一个二聚，三聚或四醇化物聚集体。这种行为对这种消除反应的立体化学结果具有重要意义。

  DOI：

  10.1002/hlca.19730560519

文献信息

• Stereochemistry of the wurtz-fittig preparation of vinylsilanes
  作者：Paul F. Hudrlik、Ashok K. Kulkarni、Sadhana Jain、Anne M. Hudrlik

  DOI：10.1016/s0040-4020(01)88586-0

  日期：1983.1

  The reactions of vinyl chlorides, bromides and iodides with sodium and trimethylsilyl chloride to give vinylsilanes have been shown to be stereospecific, with nearly complete retention of double bond configuration.

  氯乙烯，溴化物和碘化物与钠和三甲基甲硅烷基氯的反应生成乙烯基硅烷已显示具有立体特异性，几乎完全保留了双键构型。
• Ion pair formation in the addition of protic reagents to alkynes
  作者：Hilton M. Weiss、Kim M. Touchette、Gavin Jones

  DOI：10.1039/b111724f

  日期：2002.3.25

  The reaction of oct-4-yne with 20% trifluoroacetic acid and a variety of relatively weak nucleophiles in methylene chloride was found to produce a mixture of anion incorporated and solvent incorporated products. The rates of these reactions with a range of salt concentrations were found to be proportional to the rates of reaction of simple alkenes under similar conditions. The results are explained

  的反应 oct-4-yne 与20％ 三氟乙酸 和各种相对较弱的亲核试剂 二氯甲烷 被发现产生掺入阴离子的混合物，并且 溶剂合并的产品。发现这些反应的速率与一定范围的盐浓度成正比，与简单盐的反应速率成正比。烯烃在相似的条件下。与中间体的反应相反，通过形成中间离子对解释了该结果。炔烃 与溴化物或碘化物通过协同机制进行。
• Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes
  作者：Paul J. Kropp、Scott D. Crawford

  DOI：10.1021/jo00090a031

  日期：1994.6

  The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a. On extended treatment (E)-4a underwent subsequent isomerization to the thermodynamically more stable Z isomer. Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions. In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution. In contrast with solution-phase hydriodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer. E reversible arrow Z equilibration of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides 13. Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation. Surface-mediated addition of Hbr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c. Treatment of the terminal alkynes 17 and 22 with (COBr)(2) over alumina gave the dibromides 20 and 24/25,respectively, whereas use of acetyl bromide as the Hbr precursor afforded the alkenyl bromides 18b and 23.
• Kroeger; Sowa; Nieuwland, Journal of Organic Chemistry, 1936, vol. 1, p. 165
  作者：Kroeger、Sowa、Nieuwland

  DOI：——

  日期：——
• Unsaturated ketones and process for producing them
  申请人：DU PONT

  公开号：US02194704A1

  公开（公告）日：1940-03-26