cis-2-(trichloromethyl)-1-chlorocyclooctane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: cis-2-(trichloromethyl)-1-chlorocyclooctane
• 英文别名: trans-1-trichloromethyl-2-chlorocyclooctane；trans-1-chloro-2-trichloromethylcylooctane；1-chloro-2-trichloromethylcyclooctane；(1R,2R)-1-chloro-2-(trichloromethyl)cyclooctane
• 化学式: C₉H₁₄Cl₄
• 分子量: 264.022
• InChiKey: FYKGXBQOLMOWDP-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  四氯化碳 、 顺-环辛烯 在 hexacarbonyl molybdenum 作用下， 以 苯甲腈 为溶剂， 反应 4.5h， 以92%的产率得到cis-2-(trichloromethyl)-1-chlorocyclooctane
  参考文献：
  名称：

  Mo（CO）6催化在温和的反应条件下向烯烃中添加α-多卤化物

  摘要：

  发现Mo（CO）6是α-多卤化物与各种烯烃的1,2-加成反应中的有效预催化剂。明显地，该反应在温和的条件下进行，即。回流乙腈，收率令人满意。还研究了Cr（CO）6，但发现其相对于Mo配合物较差。假定活性催化物质是原位生成的（CH 3 CN）3 Mo（CO）3。检查的多卤化物为CCl 4和三氯乙酸乙酯。研究了无环以及环状烯烃和二烯。从1，5-环辛二烯开始生成取代的[3.3.0]双环辛烷的环化产物。只要相关且可行，就可以阐明加成产物的立体化学。提出了用于加成反应的催化循环。

  DOI：

  10.1016/s0022-328x(03)00238-9

文献信息

• Addition of CCl4 to olefins catalyzed by chromium and ruthenium complexes: The influence of water as a nucleophilic additive
  作者：R. I. Khusnutdinov、N. A. Schadneva、T. M. Oshnyakova、U. M. Dzhemilev

  DOI：10.1134/s0965544109040136

  日期：2009.7

  feasibility of the addition of CCl4 to linear and cyclic olefins and dienes in the presence of chromium and ruthenium complexes was established. The influence of water as a nucleophilic additive and the influence of the olefin nature, the catalyst central atom, and its ligand environment on the reaction selectivity and product yields were investigated. It was shown that the addition of water to chromium and

  建立了在铬和钌配合物存在下向直链和环状烯烃和二烯中添加CCl 4的可行性。研究了水作为亲核添加剂的影响以及烯烃性质，催化剂中心原子及其配体环境对反应选择性和产物收率的影响。结果表明，向铬和钌催化剂中加水会导致所得1,1,1,3-四氯衍生物中的氯甲基水解，产生相应的羟基衍生物并增加形成（1 + 1）加合物，这是由次氯酸的形成引起的，次氯酸是将CCl 4加至烯烃的助活化剂。
• Addition of α-polyhalides to olefins under mild reaction conditions, catalyzed by Mo(CO)6
  作者：Youval Shvo、Revital Green

  DOI：10.1016/s0022-328x(03)00238-9

  日期：2003.5

  various olefins. Significantly, the reaction was run under mild conditions, viz. refluxing acetonitrile, with satisfactory yields. Cr(CO)6 was also studied but found to be inferior relative to the Mo complex. It was assumed that the active catalytic species is (CH3CN)3Mo(CO)3, generated in situ. The polyhalides examined were CCl4 and ethyl trichloroacetate. Acyclic, as well as cyclic olefins, and dienes

  发现Mo（CO）6是α-多卤化物与各种烯烃的1,2-加成反应中的有效预催化剂。明显地，该反应在温和的条件下进行，即。回流乙腈，收率令人满意。还研究了Cr（CO）6，但发现其相对于Mo配合物较差。假定活性催化物质是原位生成的（CH 3 CN）3 Mo（CO）3。检查的多卤化物为CCl 4和三氯乙酸乙酯。研究了无环以及环状烯烃和二烯。从1，5-环辛二烯开始生成取代的[3.3.0]双环辛烷的环化产物。只要相关且可行，就可以阐明加成产物的立体化学。提出了用于加成反应的催化循环。
• Application of copper(I) halides to modifying reactivity of polyhalomethanes and arenesulfonyl chlorides in free-radical addition. “Cross-halogenation” reaction
  作者：A. S. Dneprovskii、A. N. Kasatochkin、V. P. Boyarskii、A. A. Ermoshkin、A. A. Yakovlev

  DOI：10.1134/s1070428006080033

  日期：2006.8

  In the free-radical addition of a number of organohalogen reagents to cyclic alkenes and dienes in the presence of copper(I) halides the composition of the reaction products is governed by the stage of a fast halogen transfer from the copper derivative to the alkyl radical. Under these conditions in contrast to the free-radical addition reactions initiated by UV light or peroxide initiators the intramolecular rearrangements are suppressed, the stereoselectivity of the reaction changes, and also some adducts contain halogen atoms different from those present in the organohalogen reagent employed.
• Addition of Bromotrichloromethane and Tetrachloromethane to<i>cis</i>-Cyclooctene, Cyclohexene, and Norbornadiene in the Presence of Palladium(II) Complexes
  作者：A. S. Dneprovskii†、A. A. Ermoshkin、A. N. Kasatochkin、V. P. Boyarskii

  DOI：10.1023/b:rujo.0000003181.02370.cf

  日期：2003.7

  Addition of bromotrichloromethane and tetrachloromethane to alkenes in the presence of palladium(II) complexes begins with single-electron transfer from the palladium atom to polyhalomethane molecule, followed by fragmentation of the radical anion thus formed and generation of trichloromethyl radical. Halogen transfer to a carbon-centered radical arising from addition of trichloromethyl radical at the double bond occurs both from the polyhalomethane molecule and from halide palladium complex.
• Khusnutdinov; Shchadneva; Baiguzina, Petroleum Chemistry, 2004, vol. 44, # 5, p. 350 - 357
  作者：Khusnutdinov、Shchadneva、Baiguzina、Lavrent'eva、Burangulova、Atnabaeva、Dzhemilev

  DOI：——

  日期：——