4-(1-methyl-2,2-dichlorocyclopropyl)-7,7-dichloro-1-methylbicyclo<4.1.0>heptane | 37608-28-9

• 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: 4-(1-methyl-2,2-dichlorocyclopropyl)-7,7-dichloro-1-methylbicyclo<4.1.0>heptane
• 英文别名: 7,7-Dichloro-4-(2,2-dichloro-1-methyl-cyclopropyl)-1-methyl-bicyclo[4.1.0]heptane；7,7-dichloro-4-(2,2-dichloro-1-methylcyclopropyl)-1-methylbicyclo[4.1.0]heptane
• CAS: 37608-28-9
• 化学式: C₁₂H₁₆Cl₄
• 分子量: 302.071
• InChiKey: XGSTZJHXRIKMCD-UHFFFAOYSA-N

物化性质

• 沸点：
  331.7±37.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  双戊烯 以95%的产率得到
  参考文献：
  名称：

  REGEN, S. L.;SINGH, A., J. ORG. CHEM., 1982, 47, N 8, 1587-1588

  摘要：

  DOI：

文献信息

• Calixarene-Catalyzed Generation of Dichlorocarbene and Its Application to Organic Reactions: The Catalytic Action of Octopus-Type Calix[6]arene
  作者：Eisaku Nomura、Hisaji Taniguchi、Yoshio Otsuji

  DOI：10.1246/bcsj.67.792

  日期：1994.3

  The dichlorocarbene generation reaction from CHCl3 and solid KOH in CH2Cl2 was catalyzed by the p-t-butylcalix[6]arene derivative 1 which bears six 3,6,9-trioxadecyl substituents on the phenolic oxygens. Dichlorocarbene generated by this method reacted efficiently with alkenes and amides to give dichlorocyclopropane derivatives and nitriles, respectively, in high yields. The reaction with alkadiene having isolated double bonds gave mixtures of the mono- and bis-dichlorocarbene adducts, but the monoadduct formation always predominated. The catalytic action of the calixarene and the reactivity features of dichlorocarbene generated by the above procedure are discussed on the basis of kinetic measurements. They are also compared with those of the 18-crown-6-catalyzed reactions.

  由CHCl3和固体KOH在CH2Cl2中催化生成二氯碳烯的反应是由具有六个3,6,9-三氧十烷取代基的p-叔丁基大环[6]芳烃衍生物1催化的。通过这种方法生成的二氯碳烯与烯烃和酰胺反应，分别高产率地生成二氯环丙烷衍生物和腈类物质。与具有孤立双键的烯烃二烯的反应生成单个和双二氯碳烯加成物的混合物，但单加成物的生成总是占主导地位。基于动力学测量，讨论了大环芳烃的催化作用以及上述过程中生成的二氯碳烯的反应特性，并与18-冠-6催化反应的特性进行了比较。
• Anwendungen der phasentransfer-katalyse
  作者：Eckehard V. Dehmlow、Willi Leffers

  DOI：10.1016/0022-328x(85)80132-7

  日期：1985.6

  Reflux of trimethylsilyl trichloroacetate and an alkene with the addition of a phase transfer catalyst (4 mol.%) and solid, dry potassium fluoride in an inert nonpolar solvent (toluene, chloroform, or dichloromethane) leads to dichloro- carbene adducts. This is a non-basic mild method, which can easily be carried out.

  在惰性非极性溶剂（甲苯，氯仿或二氯甲烷）中加入相转移催化剂（4摩尔％）和固体，干燥的氟化钾，使三氯乙酸三甲基甲硅烷基酯和烯烃回流，生成二氯卡宾加合物。这是一种非基本的温和方法，可以轻松执行。
• SELECTIVITY IN THE PRODUCT-DISTRIBUTION UPON THE ADDITION OF DICHLOROCARBENE TO OLEFINS BY USE OF TERTIARY AMINES AS CATALYSTS
  作者：Yoshikazu Kimura、Kakuzo Isagawa、Yoshio Otsuji

  DOI：10.1246/cl.1977.951

  日期：1977.8.5

  The dichlorocarbene species generated from chloroform and aqueous sodium hydroxide in the presence of tertiary amines exhibits a high selectivity in the product-distribution upon its addition to olefins containing multiple double bonds; the monoadducts was produced in preference to the bisadducts. The selectivity increases with decrease in the reactivity of the dichlorocarbene species.

  在叔胺的存在下，由氯仿和氢氧化钠水溶液生成的二氯卡宾物种在其加成到含有多个双键的烯烃时在产物分布中表现出高选择性；单加合物优先于双加合物产生。选择性随着二氯卡宾物种反应性的降低而增加。
• Biphasic sonochemistry. Convenient generation of dichlorocarbene
  作者：Steven L. Regen、Alok Singh

  DOI：10.1021/jo00347a047

  日期：1982.4
• DEHMLOW, E. V.;PRASHAD, M., J. CHEM. RES. SYNOP., 1982, N 12, 354-355
  作者：DEHMLOW, E. V.、PRASHAD, M.

  DOI：——

  日期：——