tetramethyl (Z,Z)-1,3-butadiene-1,2,3,4-tetracarboxylate | 65908-13-6

• 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: tetramethyl (Z,Z)-1,3-butadiene-1,2,3,4-tetracarboxylate
• 英文别名: tetramethyl (1Z,3Z)-buta-1,3-diene-1,2,3,4-tetracarboxylate
• CAS: 65908-13-6
• 化学式: C₁₂H₁₄O₈
• 分子量: 286.238
• InChiKey: BINZDSNUUKBGBJ-SFECMWDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (cyclooctadienyl)(cyclopentadienyl)ruthenium chloride 、 tetramethyl (Z,Z)-1,3-butadiene-1,2,3,4-tetracarboxylate 以 甲醇 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Cyclopentadienyl-ruthenim and -osmium chemistry

  摘要：

  Reactions between RuX(PPh3)2(eta-C5H5) (X = Cl, I) and C2(CO2Me)2 in MeOH in the presence of NH4PF6 have given three types of complex, which have been fully characterised by X-ray studies. These are the eta-4-diene complexes RuX{eta-4-CH(CO2Me) = C(CO2Me)C(CO2Me) = CH(CO2Me)}-(eta-C5H5) (1, X = Cl; 2, X = I) and the eta-5-cyclohexadienyl derivatives Ru(eta-5-C5H5){eta-5-C6H(CO2Me)6} (4) and Ru(eta-5-C5H5){eta-5-C6[C(CO2Me) = CH(CP2Me)](CO2Me)6} (5). The three complexes are formed by di-, tri- and tetra-merisation of the alkyne at the mononuclear ruthenium centre; the last reaction is unprecedented. Possible mechanisms are discussed.

  DOI：

  10.1016/0022-328x(91)80268-o
• 作为产物：
  描述：

  甲醇 、 丁炔二酸二甲酯 在 ⁺ 作用下， 反应 20.0h， 生成 苯六甲酸六甲酯 、 dimethyl 2-methoxymaleate 、 马来酸二甲酯 、 Tetramethyl (E,E)-1,3-butadiene-1,2,3,4-tetracarboxylate 、 tetramethyl (1Z,3E)-buta-1,3-diene-1,2,3,4-tetracarboxylate 、 tetramethyl (Z,Z)-1,3-butadiene-1,2,3,4-tetracarboxylate
  参考文献：
  名称：

  Reductive dimerization of dialkyl acetylenedicarboxylate catalyzed by [Rh(binap)(MeOH)2]ClO4 in methanol

  摘要：

  Cationic Rh(I) complex [Rh(binap)(MeOH)(2)]ClO4 catalyzes reductive dimerization of dialkyl acetylenedicarboxylates 1 to give 1,2,3,4-tetrakis(alkoxycarbonyl)-1,3-butadienes 2 in methanol selectively. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00507-5

文献信息

• Reductive dimerization of dialkyl acetylenedicarboxylate catalyzed by [Rh(binap)(MeOH)2]ClO4 in methanol
  作者：Kazuhide Tani、Kazuya Ueda、Kenji Arimitsu、Tsuneaki Yamagata、Yasutaka Kataoka

  DOI：10.1016/s0022-328x(98)00507-5

  日期：1998.6

  Cationic Rh(I) complex [Rh(binap)(MeOH)(2)]ClO4 catalyzes reductive dimerization of dialkyl acetylenedicarboxylates 1 to give 1,2,3,4-tetrakis(alkoxycarbonyl)-1,3-butadienes 2 in methanol selectively. (C) 1998 Elsevier Science S.A. All rights reserved.
• Cyclopentadienyl-ruthenim and -osmium chemistry
  作者：Michale I. Bruce、George A. Koutsantonis、Edward R.T. Tiekink、Brian K. Nicholson

  DOI：10.1016/0022-328x(91)80268-o

  日期：1991.12

  Reactions between RuX(PPh3)2(eta-C5H5) (X = Cl, I) and C2(CO2Me)2 in MeOH in the presence of NH4PF6 have given three types of complex, which have been fully characterised by X-ray studies. These are the eta-4-diene complexes RuXeta-4-CH(CO2Me) = C(CO2Me)C(CO2Me) = CH(CO2Me)}-(eta-C5H5) (1, X = Cl; 2, X = I) and the eta-5-cyclohexadienyl derivatives Ru(eta-5-C5H5)eta-5-C6H(CO2Me)6} (4) and Ru(eta-5-C5H5)eta-5-C6[C(CO2Me) = CH(CP2Me)](CO2Me)6} (5). The three complexes are formed by di-, tri- and tetra-merisation of the alkyne at the mononuclear ruthenium centre; the last reaction is unprecedented. Possible mechanisms are discussed.