diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate | 7417-57-4

• 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: diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate
• 英文别名: (+/-)-methylene-cyclopropane-1r,2t-dicarboxylic acid diethyl ester；(+/-)-Methylen-cyclopropan-1r,2t-dicarbonsaeure-diaethylester；(+/-)-3-Methylen-cyclopropan-dicarbonsaeure-(1r.2t)-diaethylester；Feist's ester；3-Methylen-cyclopropan-trans-1,2-dicarbonsaeure-diethylester；diethyl (1S,2S)-3-methylidenecyclopropane-1,2-dicarboxylate
• CAS: 7417-57-4；37608-33-6；55638-55-6；56221-92-2
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: VOHSAQPFAZSIES-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate 在 lithium aluminium tetrahydride 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.17h， 生成 [2,2-Bis(hydroxymethyl)-3-methylidenecyclopropyl]methanol
  参考文献：
  名称：

  Synthesis Of 2,2,3-Tris(Hydroxymethyl)Methylenecyclopropane Analogues Of Nucleosides

  摘要：

  Synthesis of 2,2,3-tris(hydroxymethyl)methylenecyclopropane analogues 16a, 16b, 17a, and 17b is described. Diethyl ester of Feist's acid 18b was hydroxymethylated via carbanion formation using formaldehyde under simultaneous isomerization to cis diester to give intermediate 19. Reduction followed by acetylation gave triacetate 22. Addition of bromine afforded reagent 23, which was used for alkylation-elimination of adenine and 2-amino-6-chloropurine to provide Z,E-isomeric mixtures of 24a and 24b. Deacetylation and separation furnished the Z-isomers 16a, 16c and E-isomers 17a, 17c. Hydrolytic dechlorination of 16c and 17c gave guanine analogues 16b and 17b. None of the analogues exhibited a significant antiviral activity. Adenosine deaminase is refractory toward adenine analogues 16a and 17a.

  DOI：

  10.1080/15257770701297000
• 作为产物：
  描述：

  Feist's acid 生成 diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate
  参考文献：
  名称：

  380.谷氨酸和酯的结构。第七部分。3-甲基环丙烯-1：2-二羧酸的衍生物

  摘要：

  DOI：

  10.1039/jr9320002557
• 作为试剂：
  描述：

  RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 在 diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以80%的产率得到
  参考文献：
  名称：

  [EN] TRANSITION METAL CARBENE COMPLEXES CONTAINING A CATIONIC SUBSTITUENT AS CATALYSTS OF OLEFIN METATHESIS REACTIONS
  [FR] COMPLEXES CARBENES DE METAUX DE TRANSITION CONTENANT UN SUBSTITUANT CATIONIQUE, UTILISES EN TANT QUE CATALYSEURS DES REACTIONS DE METATHESE DES OLEFINES

  摘要：

  提供适用于烯烃重排催化剂的有机金属配合物。这些配合物是带有阳离子取代基团的8族过渡金属卡宾，其一般结构为（I），其中M是8族过渡金属，L1和L2是中性电子给体配体，X1和X2是阴离子配体，m为0或1，n为0或1，R1、W、Y和Z如本文所定义。还提供了合成这些配合物的方法，以及将这些配合物用作烯烃重排催化剂的方法。

  公开号：

  WO2005121158A1

文献信息

• Esters of Feist's Acid: Some Insights into the Electronic Structure and Reactivity of Methylenecyclopropanes Ring-Substituted with Acceptor Groups
  作者：Vyacheslav V. Diev、Tran Q. Tung、Alexander P. Molchanov

  DOI：10.1002/ejoc.200800975

  日期：2009.2

  π-HOMO energies by substitution with an acceptor group. B3LYP calculations of addends and transition states forthe interaction of methylenecyclopropane with C,N-diphenylnitrone correctly predict regiochemical outcome. However, B3LYP calculations do not account for the observed regiochemical outcome and diminished reactivity in reactions of Feist's esters with C,N-diphenylnitrone.(© Wiley-VCH Verlag GmbH

  C-芳基-N-芳基-或N-甲基硝酮与Feist酸（3-亚甲基环丙烷-反式-1,2-二羧酸）的酯发生1,3-偶极环加成反应，形成相应的螺[环丙烷-1 ,4-异恶唑烷]环加合物作为单一异构体，产率范围为 17-59%。与未取代的亚甲基环丙烷的环加成相比，该反应以相反的区域化学结果进行。与亚甲基环丙烷相比，Feist 酯对与硝酮的环加成反应的活性明显较低，并且反应需要在高温下长时间加热。通过分子光电子能谱和理论计算 (HF/6-31G*, B3LYP/6-31G*) 研究了 Feist 酯的电子结构。两个都，Feist 酯的测量光电子 HeI 光谱和基态计算 (HF/6-31G*) 表明，通过用受体基团取代，亚甲基环丙烷 π-HOMO 能量显着降低。亚甲基环丙烷与 C,N-二苯基硝酮相互作用的加数和过渡态的 B3LYP 计算正确预测区域化学结果。然而，B3LYP 计算没有考虑观察到的区域化学结果和
• Method for the degradation of nitrile rubber by metathesis in the presence of ruthenium- or osmium-based catalysts
  申请人：Obrecht Werner

  公开号：US20070049700A1

  公开（公告）日：2007-03-01

  A novel process for the degradation of nitrile rubber by metathesis using ruthenium- or osmium-based catalysts which have both a substituted or unsubstituted imidazolidine ligand and a carbene ligand bearing a phosphonium radical is provided.

  提供了一种新的方法，通过使用基于钌或锇的催化剂进行交换反应，这些催化剂具有取代或未取代的咪唑啉配体和带有膦基基团的卡宾配体，用于降解腈橡胶。
• Goss; Ingold; Thorpe, Journal of the Chemical Society, 1923, vol. 123, p. 360
  作者：Goss、Ingold、Thorpe

  DOI：——

  日期：——
• Libermann et al., Bulletin de la Societe Chimique de France, 1954, p. 1430,1434
  作者：Libermann et al.

  DOI：——

  日期：——
• Nanometer structure and conductor mechanism of polymer modified by metal ion implantation
  作者：Yuguang Wu、Tonghe Zhang、Yanwen Zhang、Huixing Zhang、Xiaoji Zhang、Gu Zhou

  DOI：10.1007/bf02916735

  日期：2001.10

  Polyethylene terephthalate (PET) has been modified by Ag, Ti, Cu and Si ion implantation with a dose ranging from I X 10(16) to 2 x 10(17) ions/cm(2) using a metal vapor vacuum arc (MEVVA) source. The electrical properties of PET have been improved by metal ion implantation. The resistivity of implanted PET decreased obviously with an increase in ion dose. The results show that the conductive behavior of a metal ion implanted sample is different from Si-implantation samples. In order to understant the mechanism of electrical conduction, the structures of implanted layer were observed in detail by XRD and TEM. The nano carbon particles were dispersed in implanted PET. The nano metallic particles were built up in metallic ion implanted layers with dose range from 1 x 10(16) to 1 x 10(17) ions/cm(2). The nanometer metal net structure was formed in implanted layer when a dose of 2 x 10(17) ions/cm(2) is reached. Anomalous fractal growths were observed. These surface structure changes revealed conducting mechanism evolution. It is believed that the change would result in an improvement of the conductive properties. The conducting mechanism will be changed with increasing metal ion dose.