2-氯-1-甲基环丙烷-1-羧酸甲酯 | 141091-40-9

• 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
• 中文名称: 2-氯-1-甲基环丙烷-1-羧酸甲酯
• 英文名称: 2-carbomethoxy-2-methyl-1-chlorocyclopropane
• 英文别名: Methyl 2-chloro-1-methylcyclopropane-1-carboxylate
• CAS: 141091-40-9
• 化学式: C₆H₉ClO₂
• 分子量: 148.589
• InChiKey: OBZWEJATTWBOPG-UHFFFAOYSA-N

物化性质

• 沸点：
  166.3±33.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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

• 作为反应物：
  描述：

  4-chlorophenyl lithium 、 2-氯-1-甲基环丙烷-1-羧酸甲酯 以61%的产率得到
  参考文献：
  名称：

  Cyclopropane-shift type reaction of diaryl(2-halogenocyclopropyl)methanols promoted by Lewis acids

  摘要：

  Novel cyclopropane-shift type reaction of diaryl(2-halogenocyclopropyl)methanols 2b and 7 proceeded by using BF3. OEt2 and TiCl4, respectively. Utilizing these reactions, 1-aryl-3-chloro-1,2-methanoindans 5 and 9, 1-aryl-3-methylnaphthalenes 6, and 1,2-methano-1-arylindens 10 were constructed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00979-5
• 作为产物：
  描述：

  2,2-二氯-1-甲基环丙烷羧酸甲酯 在 蒽 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-氯-1-甲基环丙烷-1-羧酸甲酯
  参考文献：
  名称：

  Role of Ni(II) and Co(II) ions in the mediated reduction of gem-dichlorocyclopropanes

  摘要：

  A study has been made of the influence of Co(II) and Ni(II) ions on the kinetics of the homogeneous reduction of gem-dichlorocyclopropanes by anthracene anion radicals. It has been shown that Co(II) and Ni(II) ions accelerate this process. The observed effect depends on the nature and concentration of the metal ion and also on the type of gem-dichlorocyclopropane. Two mechanisms are examined: 1) homogeneous reduction of metal ions by anthracene anion radicals with the formation of univalent and zero-valent metals that are more effective reducing agents; and 2) activation of a dichlorocyclopropane molecule by previous coordination with a metal ion.

  DOI：

  10.1007/bf00869504

文献信息

• The trimethylsilyl substituent effect on the reactivity of silanes. Structural correlations between silyl radicals and their parent silanes
  作者：C. Chatgilialoglu、A. Guerrini、M. Lucarini

  DOI：10.1021/jo00038a031

  日期：1992.6

  Good linear correlations exist both between the bond dissociation energy of an Si-H bond and the corresponding SiH stretching frequency and between the Si-29 hyperfine splitting of a silicon-centered radical and J(Si-29-H) for the corresponding silane, when the successive substitution at the Si-H function takes place inside a family, i.e., (Me3Si)3-nSi(H)Men, n = 0-3. Explanations for these phenomena are advanced. Such structural correlations allow the characterization of (Me3Si)2Si(H)Me as a radical-based reducing agent with low hydrogen-donating abilities. Rate constants for the reaction of primary alkyl radicals with (Me3Si)2Si(H)Me have been measured over a range of temperatures by using competing unimolecular radical reactions as timing devices. The radical trapping abilities of this silane and other common radical-based reducing agents are compared.
• ——
  作者：V. V. Yanilkin、E. I. Strunskaya、N. V. Nastapova、N. I. Iaksimyuk、Z. A. Bredikhina、D. R. Sharafutdinova、A. A. Bredikhin

  DOI：10.1023/a:1024456510964

  日期：——

  Catalytic electroreduction of several substituted gem-dihalocyclopropanes was studied in the presence of metal salen-complexes by polarography, cyclic voltammetry, and preparative electrolysis. Monohalocyclopropanes (54-59%) and the corresponding allene (5-9%) were the main reduction products. The reaction rate constants were determined. The inner-sphere electron transfer was shown to occur under these conditions.
• Mediated electrochemical reduction of 1,1-dichlorocyclopropanes
  作者：V. V. Yanilkin、N. I. Maksimyuk、E. I. Gritsenko、Yu. M. Kargin

  DOI：10.1007/bf00959685

  日期：1991.1
• 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.
• 1,2-dihydro-1,2,4,3-triazaphospholo[4,5-a]quinolines as electron carriers in the electrochemical reduction of 1,1-dichloro-2-methoxycarbonyl-2-methylcyclopropane
  作者：V. V. Yanilkin、B. I. Buzykin、R. M. Eliseenkova、N. I. Maksimyuk、N. V. Nastapova

  DOI：10.1007/bf02494847

  日期：1999.11

  Electrochemical reduction of 1-X-1-R-1-5-methyl-2-phenyl-7-R-2-1,2-dihydro-1,2,4,3-triazaphospholo[4,5-a]quinolines 1-5 (1: X is the lone electron pair (LEP), R-1 = Et2N, R-2 = Me; 2: X = LEP, R-1 = Ph, R-2 = H; 3. X = S, R-1 = Et2N, R-2 = H; 4. X = LEP, R-1 = Et2N, R-2 = H; 5: X = LEP, R-1 = MeO, R-2 = H) in DMF with 0.1 M Bu4NI as supporting electrolyte is reversible and results in metastable radical anions. Radical anions of compounds 1-3 efficiently reduce 1,1-dichloro-2-methoxycarbonyl-2-methylcyclopropane both in the presence and in absence of Ni-II ions. Effective reduction rate constants have been evaluated.