endo-3-(4-chloro-phenyl)-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: endo-3-(4-chloro-phenyl)-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (1R,3S,4S)-3-(4-chlorophenyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylate
• 化学式: C₁₇H₁₇ClO₄
• 分子量: 320.773
• InChiKey: ADDWAQWVBKZYIV-MBNYWOFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  endo-3-(4-chloro-phenyl)-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid dimethyl ester 在 magnesium(II) perchlorate 作用下， 以 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  Catalysis with inorganic cations. VII. The catalytic process of the Diels-Alder reaction with magnesium perchlorate in CH2Cl2: Kinetic investigation and spectroscopic detection of the complexed intermediate

  摘要：

  The 2-arylidene-malonic acid dimethyl ester is a dienophile suitable to be coordinated by Mg(II). The formation of the dienophile/cation complex in a ratio 2:1 in a non-coordinating solvent has been demonstrated by NMR spectroscopy. Kinetic determinations performed in dichloromethane evidenced the high reactivity of the system. The high affinity for Mg(II) of the reacting dienophile allows the reaction to be performed under catalytic conditions, whose single steps have been clarified by both spectroscopic and kinetic methods. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00857-0
• 作为产物：
  描述：

  dimethyl 2-(4-chlorobenzylidene)malonate 、 环戊二烯 在 magnesium(II) perchlorate 作用下， 以 丙酮 为溶剂， 反应 288.0h， 生成 exo-3-(4-chloro-phenyl)-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid dimethyl ester 、 endo-3-(4-chloro-phenyl)-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  用无机阳离子催化。八。大环丙二酸丙二酸酯：Diels-Alder反应的合成，光谱研究和金属高氯酸盐催化

  摘要：

  大环基丙二酸酯8-10是通过Knoevenagel将不同大小的冠状丙二酸酯5-7与几种醛缩合而制得的。在存在钠，锂，钡和高氯酸镁的情况下，在几种溶剂（丙酮，乙腈和二氯甲烷）中对衍生物8-10a进行的光谱研究表明，在某些情况下会形成不同的配合物，其结构取决于阳离子和冠醚单元的尺寸。9-10的Mg（II）络合物涉及两个羰基氧原子，这种特定的相互作用对9-10b与环戊二烯之间的Diels-Alder反应具有很强的催化作用。

  DOI：

  10.1016/s0040-4020(98)00517-1

文献信息

• Catalysis with inorganic cations. VII. The catalytic process of the Diels-Alder reaction with magnesium perchlorate in CH2Cl2: Kinetic investigation and spectroscopic detection of the complexed intermediate
  作者：Giovanni Desimoni、Giuseppe Faita、Mariella Mella、Marina Ricci、PierPaolo Righetti

  DOI：10.1016/s0040-4020(97)00857-0

  日期：1997.9

  The 2-arylidene-malonic acid dimethyl ester is a dienophile suitable to be coordinated by Mg(II). The formation of the dienophile/cation complex in a ratio 2:1 in a non-coordinating solvent has been demonstrated by NMR spectroscopy. Kinetic determinations performed in dichloromethane evidenced the high reactivity of the system. The high affinity for Mg(II) of the reacting dienophile allows the reaction to be performed under catalytic conditions, whose single steps have been clarified by both spectroscopic and kinetic methods. (C) 1997 Elsevier Science Ltd.
• Catalysis with inorganic cations. VIII. Macrocyclic-yliden malonates: Synthesis, spectroscopic investigation, and metal perchlorate catalysis of the Diels-Alder reaction
  作者：Giovanni Desimoni、Giuseppe Faita、Marina Ricci、PierPaolo Righetti

  DOI：10.1016/s0040-4020(98)00517-1

  日期：1998.8

  Macrocyclic-yliden malonates 8–10 have been prepared by Knoevenagel condensation of differently sized crown malonates 5–7 with several aldehydes. The spectroscopic investigations of derivatives 8–10a in several solvents (acetone, acetonitrile, and dichloromethane) in the presence of sodium, lithium, barium, and magnesium perchlorate, evidenced, in some cases, the formation of different complexes, whose

  大环基丙二酸酯8-10是通过Knoevenagel将不同大小的冠状丙二酸酯5-7与几种醛缩合而制得的。在存在钠，锂，钡和高氯酸镁的情况下，在几种溶剂（丙酮，乙腈和二氯甲烷）中对衍生物8-10a进行的光谱研究表明，在某些情况下会形成不同的配合物，其结构取决于阳离子和冠醚单元的尺寸。9-10的Mg（II）络合物涉及两个羰基氧原子，这种特定的相互作用对9-10b与环戊二烯之间的Diels-Alder反应具有很强的催化作用。