di-(D)-menthyl (2R,3R)-[2.2.1]bicyclohept-5-ene-2,3-dicarboxylate | 125226-88-2

• 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: di-(D)-menthyl (2R,3R)-[2.2.1]bicyclohept-5-ene-2,3-dicarboxylate
• CAS: 125226-88-2
• 化学式: C₂₉H₄₆O₄
• 分子量: 458.682
• InChiKey: BVQYOJFRQWRPGV-ROCIOPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  di-(D)-menthyl (2R,3R)-[2.2.1]bicyclohept-5-ene-2,3-dicarboxylate 在 N-甲基吗啉 、 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 苯 为溶剂， 反应 15.0h， 生成 (4S)-4-phenyl-2-[(1S,2R,3R,4R)-3-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2-bicyclo[2.2.1]hept-5-enyl]-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts

  摘要：

  Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)(2)-, Zn(OTf)(2)-, and Cu(OTf)(2)-catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%. Surprisingly, a non-C-2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00323-6
• 作为产物：
  描述：

  (2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester 、 环戊二烯 在 氯化二乙基铝 作用下， 生成 di-(D)-menthyl (2R,3R)-[2.2.1]bicyclohept-5-ene-2,3-dicarboxylate
  参考文献：
  名称：

  Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts

  摘要：

  Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)(2)-, Zn(OTf)(2)-, and Cu(OTf)(2)-catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%. Surprisingly, a non-C-2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00323-6

文献信息

• Lewis-acid catalysis of the asymmetric Diels–Alder reaction of dimenthyl fumarate and cyclopentadiene
  作者：William F Kiesman、Russell C Petter

  DOI：10.1016/s0957-4166(02)00213-6

  日期：2002.6

  The effects of Lewis acid catalysts, solvent, catalyst loading, and temperature on the diastereomeric excess in the Diets-Alder reaction of (+)-dimentliyl fumarate and cyclopentadiene were investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.