(-)-[bis-(1S)-(-)-bornyl] 1,3-acetonedicarboxylate | 285128-02-1

• 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-(1S)-(-)-bornyl] 1,3-acetonedicarboxylate
• 英文别名: di-(-)-bornyl 1,3-acetonedicarboxylate；bis[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 3-oxopentanedioate
• CAS: 285128-02-1
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: LNYIUTAFOPYSPS-OVAJGEEKSA-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-(1S)-(-)-bornyl] 1,3-acetonedicarboxylate 在 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 反应 1.5h， 生成 [bis-(1S)-(-)-bornyl] 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 、 冰片 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以75%的产率得到(-)-[bis-(1S)-(-)-bornyl] 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

• Engineering Reactions in Crystalline Solids:  Radical Pairs in Crystals of Dialkyl 1,3-Acetonedicarboxylates
  作者：Zhe Yang、Miguel A. Garcia-Garibay

  DOI：10.1021/ol006042+

  日期：2000.6.1

  dialkyl succinates in high chemical yields by combination of alpha-carbonyl radical pairs produced by photochemical decarbonylation. It is proposed that the solid-state reaction depends on the exothermicity of two consecutive bond cleavage processes. It is also suggested that the efficiency of radical formation in the solid state is determined by the effect of substituents on bond dissociation energies

  结晶的1，3-丙酮二羧酸二烷基酯通过光化学脱羰作用产生的α-羰基对的组合，以高化学收率得到琥珀酸二烷基酯。提出固态反应取决于两个连续的键裂解过程的放热性。还建议固态中自由基形成的效率取决于取代基对键离解能和自由基稳定能力的影响。
• 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.