dimethyl 2-(4-piperidinophenyl)cyclopropane-1,1-dicarboxylate | 1337952-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: dimethyl 2-(4-piperidinophenyl)cyclopropane-1,1-dicarboxylate
• 英文别名: Dimethyl 2-(4-piperidin-1-ylphenyl)cyclopropane-1,1-dicarboxylate
• CAS: 1337952-17-6
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: DFHHBMRQPGVSLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(4-piperidinophenyl)cyclopropane-1,1-dicarboxylate 在 四氯化锡 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以84%的产率得到(2RS,5RS)-tetramethyl 2,5-bis(4-piperidinophenyl)cyclohexane-1,1,4,4-tetracarboxylate
  参考文献：
  名称：

  (3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings

  摘要：

  The ability of donor acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.

  DOI：

  10.1021/jo201612w
• 作为产物：
  描述：

  4-哌啶-1-基-苯甲醛 在 哌啶 、 sodium hydride 、 溶剂黄146 作用下， 以 二甲基亚砜 、 mineral oil 、 苯 为溶剂， 反应 1.58h， 生成 dimethyl 2-(4-piperidinophenyl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  (3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings

  摘要：

  The ability of donor acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.

  DOI：

  10.1021/jo201612w

文献信息

• (3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings
  作者：Olga A. Ivanova、Ekaterina M. Budynina、Alexey O. Chagarovskiy、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1021/jo201612w

  日期：2011.11.4

  The ability of donor acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.