1,1,2,2-tetrabromo-3,3-dimethylcyclopropane | 99236-10-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1,1,2,2-tetrabromo-3,3-dimethylcyclopropane
• 英文别名: 3,3-dimethyl-1,1,2,2-tetrabromocyclopropane；dimethyltetrabromide
• CAS: 99236-10-9
• 化学式: C₅H₆Br₄
• 分子量: 385.719
• InChiKey: ZMDWPFOFFADWDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  9
• 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

• 作为反应物：
  描述：

  1,1,2,2-tetrabromo-3,3-dimethylcyclopropane 在 甲基锂 作用下， 以 乙醚 为溶剂， 生成 1,2-dibromo-3,3-dimethylcyclopropene
  参考文献：
  名称：

  The generation and trapping of 1,2-Dibromo-3-methylbut-2-en-1-ylidenes

  摘要：

  1,2-Dibromo-3,3-dimerhylcyclopropene, generated by debromination of 1,1,2,2-tetrabromo-3,3-dimethylcyclopropane on reaction with methyllithium, ring-opens at 0-20 degrees C to produce 1,2-dibromo-3-methylbut-2-en-1-ylidene. This is trapped by alkenes to give vinylcyclopropanes. In the case of electron rich alkenes, the stereochemistry is retained in the product, suggesting that a singlet carbene is involved. In the case of alpha,beta-unsaturated esters, ketones or nitriles, the major cyclopropane produced has the vinyl and electron-withdrawing groups cis-related. 3-(2-Methoxy-ethyl)-3-methyl- and 3-(2-bromoethyl)-3-methyl-1,2-dibromocyclopropenes also ring-open at ambient temperature but little stereoselectivity is observed in the trapping of the derived vinyl-carbenes by alkenes. The reaction of 3-(2-hrdroxrethyl)-3-methyl-1,1,2,2-tetrabromocyclopropane with methyl lithium or diethylphosphite and triethylamine does not lead to an isolable cyclo-propene, but instead to Z-1,2-dibromo-3-methylbuta-1,3-diene; quenching with deuterium oxide at low temperature leads to the incorporation of deuterium at C-1.

  DOI：

  10.1016/0040-4020(95)00448-h
• 作为产物：
  描述：

  1,1-二溴-2-甲基丙-1-烯 、 三溴甲烷 在 sodium hydroxide 、 十六烷基三甲基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以50%的产率得到1,1,2,2-tetrabromo-3,3-dimethylcyclopropane
  参考文献：
  名称：

  The generation and trapping of 1,2-Dibromo-3-methylbut-2-en-1-ylidenes

  摘要：

  1,2-Dibromo-3,3-dimerhylcyclopropene, generated by debromination of 1,1,2,2-tetrabromo-3,3-dimethylcyclopropane on reaction with methyllithium, ring-opens at 0-20 degrees C to produce 1,2-dibromo-3-methylbut-2-en-1-ylidene. This is trapped by alkenes to give vinylcyclopropanes. In the case of electron rich alkenes, the stereochemistry is retained in the product, suggesting that a singlet carbene is involved. In the case of alpha,beta-unsaturated esters, ketones or nitriles, the major cyclopropane produced has the vinyl and electron-withdrawing groups cis-related. 3-(2-Methoxy-ethyl)-3-methyl- and 3-(2-bromoethyl)-3-methyl-1,2-dibromocyclopropenes also ring-open at ambient temperature but little stereoselectivity is observed in the trapping of the derived vinyl-carbenes by alkenes. The reaction of 3-(2-hrdroxrethyl)-3-methyl-1,1,2,2-tetrabromocyclopropane with methyl lithium or diethylphosphite and triethylamine does not lead to an isolable cyclo-propene, but instead to Z-1,2-dibromo-3-methylbuta-1,3-diene; quenching with deuterium oxide at low temperature leads to the incorporation of deuterium at C-1.

  DOI：

  10.1016/0040-4020(95)00448-h

文献信息

• Baird, Mark. S.; Nethercott, William; Slowey, Paul D., Journal of Chemical Research, Miniprint, 1985, # 12, p. 3815 - 3829
  作者：Baird, Mark. S.、Nethercott, William、Slowey, Paul D.

  DOI：——

  日期：——
• Dulayymi, Juma'a R. Al; Baird, Mark S.; Bolesov, Ivan G., Journal of the Chemical Society. Perkin transactions II, 2000, # 7, p. 1603 - 1618
  作者：Dulayymi, Juma'a R. Al、Baird, Mark S.、Bolesov, Ivan G.、Nizovtsev, Alexey V.、Tverezovsky, Viacheslav V.

  DOI：——

  日期：——
• Dulayymi, Ahmad R. Al; Baird, Mark S., Journal of the Chemical Society. Perkin transactions I, 1994, # 12, p. 1547 - 1548
  作者：Dulayymi, Ahmad R. Al、Baird, Mark S.

  DOI：——

  日期：——
• A simple and efficient hydrodehalogenation of 1,1-dihalocyclopropanes
  作者：Juma'a R. Al Dulayymi、Mark S. Baird、Ivan G. Bolesov、Viacheslav Tveresovsky、Michael Rubin

  DOI：10.1016/s0040-4039(96)02051-5

  日期：1996.12

  1,1-Dibromo- and 1,1-dichlorocyclopropanes are converted into the corresponding monohalo-cyclopropanes (as mixtures of stereoisomers where appropriate) by reaction with 1.2-1.3 mol. equiv. of ethyl magnesium bromide and a snell amount of titanium isopropoxide in ether. In the presence of an excess of ethylmagnesium bromide the product from the dibromide is the non- halogenated cyclopropane. Copyright (C) 1996 Elsevier Science Ltd
• Baird, Mark S.; Hussain, Heimi H., Journal of Chemical Research, Miniprint, 1988, # 9, p. 2301 - 2312
  作者：Baird, Mark S.、Hussain, Heimi H.

  DOI：——

  日期：——