[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate | 84235-35-8

• 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] (1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 84235-35-8
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: NUXWNOJUDXSANL-IFTGGNMHSA-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

• 作为反应物：
  描述：

  [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate 生成 exo-5-norbornenecarboxylic acid
  参考文献：
  名称：

  AXMEDOV, I. M.;MAMEDOV, EH. G.;GUSEJNOV, M. M.;GULIEVA, K. A.

  摘要：

  DOI：
• 作为产物：
  描述：

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

  AXMEDOV, I. M.;MAMEDOV, EH. G.;GUSEJNOV, M. M.;GULIEVA, K. A.

  摘要：

  DOI：

文献信息

• Practical enantioselective Diels-Alder and aldol reactions using a new chiral controller system
  作者：E. J. Corey、Rene Imwinkelried、Stanislaw Pikul、Yi Bin Xiang

  DOI：10.1021/ja00196a081

  日期：1989.7

  Catalyse par le complexe cyclique Al [−N(SO 2 CF 3 )(CHPh) 2 (CF 3 SO 2 )N-] R, R=i-Bu, CH 3

  催化par le complexe cyclique Al [-N(SO 2 CF 3 )(CHPh) 2 (CF 3 SO 2 )N-] R, R=i-Bu, CH 3
• 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。
• 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.
• The effect of alumina on the Diels-Alder reactions of cyclopentadiene with menthyl acrylate and dimenthyl fumarate.
  作者：George W. Kabalka、Richard M. Pagni、Satinder Bains、George Hondrogiannis、Miechelle Plesco、Robert Kurt、Danielle Cox、James Green

  DOI：10.1016/s0957-4166(00)80026-9

  日期：1991.1

  Alumina catalyzes the Diels-Alder reactions of cyclopentadiene with optically active menthyl acrylate and dimenthyl fumarate. Significant diastereoselectivity is observed in each case.