gem-2-bromo-2-phenyl-1,1-dichlorocyclopropane | 115525-21-8

• 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: gem-2-bromo-2-phenyl-1,1-dichlorocyclopropane
• 英文别名: 2-bromo-2-phenyl-gem-dichlorocyclopropane；2-Bromo-2-phenyl-1,1-dichlorocyclopropane；(1-bromo-2,2-dichlorocyclopropyl)benzene
• CAS: 115525-21-8
• 化学式: C₉H₇BrCl₂
• 分子量: 265.965
• InChiKey: NTUMBKNDAOMTGE-UHFFFAOYSA-N

物化性质

• 沸点：
  291.4±40.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  gem-2-bromo-2-phenyl-1,1-dichlorocyclopropane 、 邻甲酚 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以69%的产率得到1,1'-[(1-phenylprop-1-yne-3,3-diyl)bis(oxy)]bis(2-methylbenzene)
  参考文献：
  名称：

  2-溴-2-苯基-1,1-二氯环丙烷与酚和醇的反应

  摘要：

  150 我们最近表明，在与一元和二元酚的反应中，取代的二氯环丙烷在第一阶段转化为具有环外双键的化合物。后者，由于反应性氯烯丙基部分的存在，容易与羟基反应形成相应的环丙酮缩酮 [1]。研究 2 溴 2 苯基 1,1 二氯环丙烷 (I) 在这些条件下的转化很有趣，它很容易通过可用的 α 溴苯乙烯与二氯卡宾反应形成 [2]。

  DOI：

  10.1134/s0012500812080022
• 作为产物：
  描述：

  alpha- 溴苯乙烯 在 二氯甲烷 作用下， 以 正己烷 为溶剂， 生成 gem-2-bromo-2-phenyl-1,1-dichlorocyclopropane
  参考文献：
  名称：

  Kostikov, R. R.; Drygailova, E. A.; Golovkina, E. A., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 1917 - 1920

  摘要：

  DOI：

文献信息

• Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.
  作者：Leiv K. Sydnes、Einar Bakstad、Morten Heide、Georg W. Jensen、Inge L. Møller、Ruby I. Nielsen、Carl Erik Olsen、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0446

  日期：——

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.
• Raskildina, Gulnara Z.; Aminova, Elmira K.; Kazakova, Anna N., Revue Roumaine de Chimie, 2013, vol. 58, # 6, p. 497 - 500
  作者：Raskildina, Gulnara Z.、Aminova, Elmira K.、Kazakova, Anna N.、Bogomazova, Anna A.、Mikhailova, Natalia N.、Zlotsky, Simon S.

  DOI：——

  日期：——
• Alkylation of aromatic hydrocarbons with 2-bromo-2-phenyl-gem-dichlorocyclopropane
  作者：E. K. Kurbankulieva、A. N. Kazakova、L. V. Spirikhin、S. S. Zlotskii

  DOI：10.1134/s107036321306008x

  日期：2013.6

  The alkylation of aromatic hydrocarbons with 2-bromo-2-phenyl-gem-dichlorocyclopropane in the presence of catalytic quantities of aluminum chloride was found to afford the corresponding 2-aryl-3-phenyl-1,1-dichloroprop-1-enes. It was shown that the yield of the alkylation products depended on the nature of substituents in the aromatic ring. Compared with the thermal heating, microwave irradiation allows reducing the reaction time and increasing the yield of the corresponding 2-aryl-3-phenyl-1,1-di-chloroprop-1-enes, wherein the ortho-/para-isomers ratio changes.
• Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.
  作者：Einar Bakstad、Leiv K. Sydnes、Anders Kjær、Salka E. Nielsen、Carl E. Olsen、Kirsi Ranta、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1029

  日期：——

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.
• KOSTIKOV, R. R.;DRYGAJLOVA, E. A.;GOLOVKINA, E. A.;KOMENDANTOV, A. M.;MOL+, ZH. ORGAN. XIMII, 23,(1987) N 10, 2170-2174
  作者：KOSTIKOV, R. R.、DRYGAJLOVA, E. A.、GOLOVKINA, E. A.、KOMENDANTOV, A. M.、MOL+

  DOI：——

  日期：——