diethyl 2-(3-bromo-2,4,6-trimethoxyphenyl)cyclopropane-1,1-dicarboxylate | 1337952-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2-(3-bromo-2,4,6-trimethoxyphenyl)cyclopropane-1,1-dicarboxylate
• CAS: 1337952-16-5
• 化学式: C₁₈H₂₃BrO₇
• 分子量: 431.28
• InChiKey: SPXFCKJOGWVGLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2-(3-bromo-2,4,6-trimethoxyphenyl)cyclopropane-1,1-dicarboxylate 在 四氯化锡 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 以81%的产率得到(2RS,5RS)-tetraethyl 2,5-bis(3-bromo-2,4,6-trimethoxyphenyl)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：

  diethyl 2-(2,4,6-trimethoxybenzylidene)malonate 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.58h， 生成 diethyl 2-(3-bromo-2,4,6-trimethoxyphenyl)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.