[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1S,2R,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylate | 138752-04-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1S,2R,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 138752-04-2
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: NUXWNOJUDXSANL-PHPOFCCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯酸-L-薄荷酯 、 环戊二烯 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 生成 (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate 、 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1S,2R,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  High viscosity of ionic liquids causes rate retardation of Diels-Alder reactions

  摘要：

  已确定三种双分子Diels-Alder反应的二级反应速率常数k₂，以证明离子液体的高粘度在作为溶剂介质进行Diels-Alder反应时可能是一个不利特性。如果在纯离子液体中混入共溶剂，可以提高反应速率。

  DOI：

  10.1007/s11426-012-4684-9

文献信息

• Effect of clay calcination on clay-catalysed Diels-Alder reactions of cyclopentadiene with methyl and (−)-menthyl acrylates
  作者：Carlos Cativiela、José M. Fraile、José I. García、José A. Mayoral、Elisabeth Pires、François Figueras、Louis C. de Mènorval

  DOI：10.1016/s0040-4020(01)88236-3

  日期：1992.1

  10-montmorillonites, activated by several methods, are used as catalysts in the reaction between methyl acrylate and cyclopentadiene. Calcined clays are better catalysts than dried clays. Zn(II) clays, dried and calcined, are compared as catalysts of the asymmetric Diels-Alder reaction between (−)-methyl acrylate and cyclopentadiene. Calcined clay again shows a higher catalytic activity and leads to better

  通过几种方法活化的Zn（II）和Fe（III）交换的K 10蒙脱石在丙烯酸甲酯和环戊二烯之间的反应中用作催化剂。煅烧粘土比干粘土是更好的催化剂。比较干燥和煅烧的Zn（II）粘土作为（-）-丙烯酸甲酯和环戊二烯之间不对称Diels-Alder反应的催化剂。煅烧的粘土再次显示出较高的催化活性，并导致更好的非对映异构体过量百分比。此外，煅烧的粘土易于回收而没有催化性能的损失。
• Clay-catalysed asymmetric diels-alder reaction of cyclopentadiene with (−)-menthyl acrylate
  作者：C. Cativiela、F. Figuerasb、J.M. Frailea、J.I. Garcia、J.A. Mayorala

  DOI：10.1016/s0957-4166(00)86134-0

  日期：1991.1

  Zn(II)-exchanged K10 montmorillonite is shown to be an efficient catalyst for the reaction between cyclopentadiene and (−)-menthyl acrylate, leading to the 1R,2R-cycloadduct with good chemical yield, high % d.e. and excellent endo/exo selectivity.

  Zn（II）交换的K10蒙脱土被证明是环戊二烯与丙烯酸（-）-薄荷基酯之间反应的有效催化剂，从而产生了1R，2R-环加合物，具有良好的化学收率，高％de和内/外选择性。
• The reaction of optically active menthyl acrylate with cyclopentadiene on γ-alumina
  作者：George Hondrogiannis、Richard M. Pagni、George W. Kabalka、Robert Kurt、Danielle Cox

  DOI：10.1016/s0040-4039(00)79909-6

  日期：1991.5

  The Diels-Alder reaction of optically active menthyl acrylate with cyclopentadiene is catalyzed by γ-alumina. The reaction is very selective, yielding large endo to exo ratios of products and diasteroemeric excesses for the endo adduct.

  γ-氧化铝催化旋光丙烯酸薄荷酯与环戊二烯的Diels-Alder反应。该反应是非常选择性的，产生较大的内-外比的产物和内加合物的非对映异构体过量。
• ——
  作者：E.G. Mamedov

  DOI：10.1023/a:1012374828303

  日期：——

  An asymmetrical synthesis of bicyclo[2.2.1]hept-2-enes is described performed by [4+21-cyclo-addition of (-)-menthyl acrylate and (-)-menthyl methacrylate to cyclopentadiene in the presence of BBr3. The effect of different factors on isomer composition, yield, and enantiomeric purity of the compounds obtained was investigated. Kovatch indices were determined and boiling points were estimated with the use of gas-liquid chromatography.
• Silica and alumina modified by Lewis acids as catalysts in Diels-Alder reactions of chiral acrylates
  作者：Carlos Cativiela、François Figueras、José I. García、José A. Mayoral、Elisabet Pires、Ana J. Royo

  DOI：10.1016/s0957-4166(00)80163-9

  日期：1993.4

  Silica and alumina, modified by treatment with AlClEt2 and TiCl4, are tested as catalysts in the reactions of cyclopentadiene (1) with (-)-menthyl acrylate (2a), (R)-O-acryloyl pantolactone (2b) and (S)-O-acryloyl lactate (2c). Silica-modified systems are the most efficient heterogeneous catalysts described to date for this kind of reaction, leading to selectivities similar to those obtained with aluminium homogeneous catalysts. Whereas silica. AlClEt2 is better for the reaction of 2a and 2c, silica. TiCl4 is more suitable for the reaction of 2b.