ethyl trans-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate | 97149-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl trans-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate
• 英文别名: trans ethyl 2,2-dimethoxy-3-methylcyclopropane-1-carboxylate；trans-ethyl 2,2-dimethoxy-3-methylcyclopropane-1-carboxylate；trans-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate；ethyl (1R,3R)-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate
• CAS: 97149-52-5；130307-20-9
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: BRQVWVDQCXJKSK-RQJHMYQMSA-N

物化性质

• 沸点：
  33 °C(Press: 0.1 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl trans-2,2-dimethoxy-3-methylcyclopropane-1-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到Ethyl 3-methoxycarbonyloxybutanoate
  参考文献：
  名称：

  Reaction of ethyl 2,2-dimethoxycyclopropanecarboxylates with m -CPBA. Discovery of two new related degradative processes leading to β-hydroxyacid derivatives

  摘要：

  The reaction of the 3-alkyl-substituted and 3,3-dialkyl-substituted ethyl 2,2-dimethoxycyclopropanecarboxylates 1-3 with m-CPBA in CH2Cl2 leads to the formation of the beta -hydroxyacid derivatives 4-6 via two related processes involving the scission of both the C-1-C-2 and C-2-C-3 bonds and consequently to the degradation of the original cyclopropane carbon skeleton (extrusion of the C-2 carbon). Cis- and trans-2-ethoxycyclopropanecarboxylic acid ethyl esters 9 and 10, respectively, structurally related to 1-3, are unreactive under the same conditions. A hypothesis explaining the observed reactivity is formulated. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01892-x
• 作为产物：
  描述：

  甲基烯酮二甲基缩醛 、 重氮乙酸乙酯 以44%的产率得到
  参考文献：
  名称：

  GRAZIANO, M. L.;SCARPATI, R., J. CHEM. SOC. PERKIN TRANS., 1985, N 2, 289-294

  摘要：

  DOI：

文献信息

• Oxidative scission of ethyl 2,2-dimethoxycyclopropanecarboxylates with lead tetraacetate. Synthesis of the unusual anhydride bis-acetals
  作者：M.Liliana Graziano、Vincenzo Piccialli

  DOI：10.1016/s0040-4039(99)01776-1

  日期：1999.11

  The reaction of ethyl 2,2-dimethoxycyclopropanecarboxylates 1–3 with lead tetraacetate (Pb(OAc)4, LTA) in benzene leads to the oxidative scission of the C1C2 bond. Monoalkylated fumric acid diesters 4 and 5 are obtained from 3-alkylcyclopropanes 1 and 2, respectively, along with dimeric species for which we propose the unusual anhydride bis-acetal structure 6 or 7, respectively. Reaction of 3,3-dimethylcyclopropane

  乙基2,2- dimethoxycyclopropanecarboxylates的反应1-3用四乙酸铅（铅（OAC）4在苯引线，LTA）到C的氧化断链1 C 2键。单烷基化的烟酸二酯4和5分别从3-烷基环丙烷1和2以及二聚体得到，我们分别针对二聚体提出了不同寻常的酸酐双缩醛结构6或7。3，3-二甲基环丙烷3与LTA的反应产生3-乙酰基琥珀酸酯衍生物8作为唯一的反应产物。
• Bromination and iodination of donor–acceptor cyclopropanes. Evidence for an ET mechanism
  作者：Vincenzo Piccialli、M.Liliana Graziano、M.Rosaria Iesce、Flavio Cermola

  DOI：10.1016/s0040-4039(02)01966-4

  日期：2002.11

  presence of pyridine, NBS, trimethyl phosphate, and iodination with ICl and ICl/pyridine has been also performed. A common SET mechanism may be proposed for both halogenations; depending on the reaction conditions, bromination can also occur via acid-catalysed or SE2 routes. The reaction of the 2-ethoxyanalogues cis-12 and trans-12 with the same halogens proceeds in a similar manner, giving 3-formyl-2-haloesters

  2,2-二甲氧基环丙烷甲酸乙酯1a – d容易与Br 2和I 2在CCl 4或CH 2 Cl 2中反应，高产率地分别生成1-乙基-4-甲基2-卤代丁二酸酯2和3。还已经在吡啶，NBS，磷酸三甲酯存在下进行溴化，并用ICl和ICl /吡啶进行碘化。对于两种卤化，可以提出通用的SET机制。取决于反应条件，也可以通过酸催化的或S发生溴化ë 2个路由。2- ethoxyanalogues的反应顺- 12和反式- 12用相同的卤素前进以类似的方式，得到3-甲酰基-2-卤代酯与相应的diethylacetals作为主要产物一起。还研究了用催化体系NaI / m -CPBA / 18-crown-6对12的碘化。
• Ring-opening reactions of cyclopropanes. Part 7.1 Selenenylation and cyanoselenenylation of ethyl 2,2-dimethoxycyclopropanecarboxylates
  作者：M. Liliana Graziano、M. Rosaria Iesce、Flavio Cermola、Giovanni Caputo、Fulvio De Lorenzo

  DOI：10.1039/b109480g

  日期：2002.2.22

  1a. The presence of TiCl4 influences the stereochemistry of the reaction with chloride 3 while it is essential for reaction of the less reactive PhSeCN 4. With this electrophile the reactions lead to α,α-dimethoxycarbonitriles 13a–d while only 1a and 1b give also the expected cyanoselenenyl derivatives 12a and 12b. Moreover, from 1b compound syn- 5b is obtained, and 1a gives, via the alkene 2a, esters

  C3取代的未催化反应 环丙烷 1b–d与苯硒烯基氯3生成1-乙基4-甲基2-（苯基硒代）丁二酸酯5b–d，而未取代的1a得到3-苯基硒代衍生物6a。的形成图5b-d发生区域选择性和立体选择性地通过的电开环1而图6a从的所述selenenylation结果烯烃 通过1a的异构化形成2a。TiCl 4的存在会影响与氯化物3的反应的立体化学，而这对于反应性较低的PhSeCN 4的反应必不可少。通过这种亲电试剂，反应生成α，α-二甲氧基腈13a-d，而只有1a和1b也给出了预期的氰基亚烯基衍生物12a和12b。此外，从图1b化合物顺-图5b中获得，和1a中给出，通过所述烯烃 2A，酯类 14a和6a。机理解释表明，稳定的偶极物质9的中间体应通过路易斯酸与碳酸的配位而形成。羰1的氧和随后的开环。
• Graziano, M. Liliana; Scarpati, Rachele, Journal of the Chemical Society. Perkin transactions I, 1985, p. 289 - 294
  作者：Graziano, M. Liliana、Scarpati, Rachele

  DOI：——

  日期：——
• Cermola, Flavio; Di Gioia, Lucrezia; Graziano, Maria Liliana, Journal of Chemical Research, 2005, # 10, p. 677 - 681
  作者：Cermola, Flavio、Di Gioia, Lucrezia、Graziano, Maria Liliana、Iesce, Maria Rosaria

  DOI：——

  日期：——