(-)-[bis-(1R)-(-)-isobornyl] 1,3-acetonedicarboxylate | 922148-91-2

• 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: (-)-[bis-(1R)-(-)-isobornyl] 1,3-acetonedicarboxylate
• 英文别名: bis[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 3-oxopentanedioate
• CAS: 922148-91-2
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: LNYIUTAFOPYSPS-DEJDVFSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-[bis-(1R)-(-)-isobornyl] 1,3-acetonedicarboxylate 在 1,3-dimethylimidazolin-3-ium hexafluorophosphate 、 三乙胺 作用下， 以 正己烷 为溶剂， 反应 1.5h， 以89%的产率得到(R)-(-)-[bis-(1R)-(-)-isobornyl] 2,3-pentadienedioate
  参考文献：
  名称：

  A practical improvement of crystallization-induced asymmetric transformation of allene-1,3-dicarboxylates

  摘要：

  Enantiomerically pure allene-1,3-dicarboxylates were easily synthesized by using epimerization-crystallization of dissymmetric allene compounds, which were prepared from acetone-1,3-dicarboxylates and naturally abundant chiral alcohols, that is, (-)and (+)-menthols, borneol, and isoborneol. After scrutinizing the crystallization of several allene-1,3-dicarboxylates in the presence of triethylamine, it was found that allene-1,3-dicarboxylate carrying bornyl groups was the most easily prepared as a single isomer because of it having suitable solubility to be crystallized in hexane at 0 degrees C to room temperature. Diels-Alder reaction of the enantiomerically pure allene-1,3-dicarboxylates and cyclic dienes, such as N-Boc-pyrrole and cyclopentadiene, afforded endo-adducts having the same configurations at two newly generated stereogenic centers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.004
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 isoborneol 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以76%的产率得到(-)-[bis-(1R)-(-)-isobornyl] 1,3-acetonedicarboxylate
  参考文献：
  名称：

  A practical improvement of crystallization-induced asymmetric transformation of allene-1,3-dicarboxylates

  摘要：

  Enantiomerically pure allene-1,3-dicarboxylates were easily synthesized by using epimerization-crystallization of dissymmetric allene compounds, which were prepared from acetone-1,3-dicarboxylates and naturally abundant chiral alcohols, that is, (-)and (+)-menthols, borneol, and isoborneol. After scrutinizing the crystallization of several allene-1,3-dicarboxylates in the presence of triethylamine, it was found that allene-1,3-dicarboxylate carrying bornyl groups was the most easily prepared as a single isomer because of it having suitable solubility to be crystallized in hexane at 0 degrees C to room temperature. Diels-Alder reaction of the enantiomerically pure allene-1,3-dicarboxylates and cyclic dienes, such as N-Boc-pyrrole and cyclopentadiene, afforded endo-adducts having the same configurations at two newly generated stereogenic centers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.004

文献信息

• A practical improvement of crystallization-induced asymmetric transformation of allene-1,3-dicarboxylates
  作者：Takahiro Katoh、Chie Noguchi、Hiroyuki Kimura、Toshio Fujiwara、Shogo Ichihashi、Kiyoharu Nishide、Tetsuya Kajimoto、Manabu Node

  DOI：10.1016/j.tetasy.2006.11.004

  日期：2006.11

  Enantiomerically pure allene-1,3-dicarboxylates were easily synthesized by using epimerization-crystallization of dissymmetric allene compounds, which were prepared from acetone-1,3-dicarboxylates and naturally abundant chiral alcohols, that is, (-)and (+)-menthols, borneol, and isoborneol. After scrutinizing the crystallization of several allene-1,3-dicarboxylates in the presence of triethylamine, it was found that allene-1,3-dicarboxylate carrying bornyl groups was the most easily prepared as a single isomer because of it having suitable solubility to be crystallized in hexane at 0 degrees C to room temperature. Diels-Alder reaction of the enantiomerically pure allene-1,3-dicarboxylates and cyclic dienes, such as N-Boc-pyrrole and cyclopentadiene, afforded endo-adducts having the same configurations at two newly generated stereogenic centers. (c) 2006 Elsevier Ltd. All rights reserved.