(Z)-dimethyl 2-ethylidenesuccinate | 42162-52-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-dimethyl 2-ethylidenesuccinate
• 英文别名: Butanedioic acid, ethylidene-, dimethyl ester；dimethyl (2Z)-2-ethylidenebutanedioate
• CAS: 42162-52-7
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: LXCMQQYLYFQEFQ-XQRVVYSFSA-N

物化性质

• 沸点：
  218.2±15.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基-2-亚甲基丁酸甲酯 在 palladium diacetate 、 三苯基膦 吡啶 、 4-二甲氨基吡啶 作用下， 以 苯 为溶剂， 25.0~50.0 ℃ 、2.03 MPa 条件下， 反应 15.0h， 生成 (Z)-dimethyl 2-ethylidenesuccinate
  参考文献：
  名称：

  Stereochemical study on the palladium(O)-catalyzed carbonylation of 3-(methoxycarbonyloxy)-2-methylenealkanoates and analogues

  摘要：

  A series of 3-(alkoxycarbonyloxy)-2-methylenealkanoate (1), a sulfonate (5), and an N,N-dimethylamide (6) were carbonylated using Pd(0) complexes as catalyst to give alkylidenesuccinate (2), and analogues in moderate to good yields. The stereoselectivity for E and Z isomers of carbonylation products was found to differ remarkably, depending on the three types of substrates which always include an electron-withdrawing group. The results are explained in terms of the plausible MM2 simulation through the model compounds.

  DOI：

  10.1016/s0040-4020(01)88755-x

文献信息

• Catalytic Amide-Mediated Methyl Transfer from Silanes to Alkenes in Fujiwara–Moritani Oxidative Coupling
  作者：Waqar Rauf、John M. Brown

  DOI：10.1002/anie.200800815

  日期：2008.5.19
• Hartmann,W. et al., Chemische Berichte, 1973, vol. 106, p. 1076 - 1082
  作者：Hartmann,W. et al.

  DOI：——

  日期：——
• Ballini Roberto, Bosica Giovanna, Tetrahedron, 51 (1995) N 14, S 4213-4222
  作者：Ballini Roberto, Bosica Giovanna

  DOI：——

  日期：——
• Stereochemical study on the palladium(O)-catalyzed carbonylation of 3-(methoxycarbonyloxy)-2-methylenealkanoates and analogues
  作者：Shu-Zhong Wang、Keiji Yamamoto、Harou Yamada、Takashi Takahashi

  DOI：10.1016/s0040-4020(01)88755-x

  日期：1992.3

  A series of 3-(alkoxycarbonyloxy)-2-methylenealkanoate (1), a sulfonate (5), and an N,N-dimethylamide (6) were carbonylated using Pd(0) complexes as catalyst to give alkylidenesuccinate (2), and analogues in moderate to good yields. The stereoselectivity for E and Z isomers of carbonylation products was found to differ remarkably, depending on the three types of substrates which always include an electron-withdrawing group. The results are explained in terms of the plausible MM2 simulation through the model compounds.