trans-1-bromo-2-carbomethoxy-2-methylcyclopropane | 58683-50-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-1-bromo-2-carbomethoxy-2-methylcyclopropane
• 英文别名: methyl (E)-2-bromo-1-methylcyclopropanoate；methyl trans-2-bromo-1-methylcyclopropanecarboxylate；(E)-2-Brom-1-methyl-cyclopropancarbonsaeure-methylester；trans-Methyl-2-bromo-1-methylcyclopropancarboxylat；methyl (1S,2R)-2-bromo-1-methylcyclopropane-1-carboxylate
• CAS: 58683-50-4
• 化学式: C₆H₉BrO₂
• 分子量: 193.04
• InChiKey: IQHRBUGQFSFNHZ-INEUFUBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 2,2-dibromo-1-methylcyclopropanecarboxylate 在 异丙基溴化镁 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以10%的产率得到
  参考文献：
  名称：

  功能化的α-溴环丙基溴化镁：生成和一些反应

  摘要：

  的功能衍生物，宝石-dibromocyclopropanes（醚和酯宝石dibromocyclopropylmethanol，2,2- dibromocyclopropanecarboxylic酸和它们的酯）采取与异丙基溴化镁的治疗经受局部hydrodebromination（3-6摩尔-当量）的THF，然后在甲醇中在- 60°C时可获得相应的一溴化物，收率为64–95％。向反应混合物中添加非溶剂化的溴化镁会导致格氏试剂的量显着减少（从6摩尔当量降至3摩尔当量）。这允许实现2，2-二溴环丙烷羧酸的部分加氢脱溴。

  DOI：

  10.1134/s1070428013110043

文献信息

• Kirmse, Wolfgang; Rode, Jutta; Rode, Klaus, Chemische Berichte, 1986, vol. 119, # 12, p. 3672 - 3693
  作者：Kirmse, Wolfgang、Rode, Jutta、Rode, Klaus

  DOI：——

  日期：——
• Reaction of gem-dibromocyclopropanes with potassium dimethyl phosphite in liquid ammonia. A highly stereoselective reduction
  作者：Gordon F. Meijs、Ian R. Doyle

  DOI：10.1021/jo00220a008

  日期：1985.10
• A novel system consisting of low valent vanadium and diethyl phosphonate or triethyl phosphite for the highly stereoselective reduction of gem-dibromocyclopropanes
  作者：Toshikazu Hirao、Keisuke Hirano、Takeya Hasegawa、Yoshiki Ohshiro、Isao Ikeda

  DOI：10.1021/jo00075a070

  日期：1993.11
• Sydnes, Leiv K.; Hemmingsen, Tor H., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 2, p. 93 - 102
  作者：Sydnes, Leiv K.、Hemmingsen, Tor H.

  DOI：——

  日期：——
• Electrochemical reduction of 1,1-dihalo-2,2-disubstituted cyclopropanes
  作者：Yu. M. Kargin、E. I. Gritsenko、V. V. Yanilkin、V. V. Plemenkov、L. K. Dubovik、N. I. Maksimyuk、B. M. Garifullin、Sh. K. Letypov、A. V. Il'yasov

  DOI：10.1007/bf00863575

  日期：1992.9

  The electrochemical reduction of 1,1-dihalo-2-R-2-methylcyclopropanes was studied by polarography and preparative electrolysis. A mixture of stereoisomeric monoboro- and monochlorocyclopropanes was obtained with preparative yield of 60-70% in preparative electroreduction in methanol against a background of 0.1 M LiClO4. In the case of bromine derivatives of cyclopropanes (except when R = CN) an effect was found on the part of the current density on the ratio of cis and trans isomers, which was interpreted as a change, in dependence on current density, of the contributions of the reactions of reduction of the starting compounds (SN2 mechanism) and ionic pairs (S(N)1 mechanism). The effect of the solvent (CHCl3, DMF, DMSO, MeOH) and background salt (LiClO4, Et4NBr) on the ratio of stereoisomers is in agreement with this interpretation.