(1S,2S,3E,4R)-(+)-[(1S)-(-)-bornyl] 3-[2-(-)-bornyloxy-2-oxoethylidene]-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-5-ene-2-carboxylate | 922148-95-6

• 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: (1S,2S,3E,4R)-(+)-[(1S)-(-)-bornyl] 3-[2-(-)-bornyloxy-2-oxoethylidene]-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
• 英文别名: 7-O-tert-butyl 2-O-[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (1S,2S,3E,4R)-3-[2-oxo-2-[[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]oxy]ethylidene]-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate
• CAS: 922148-95-6
• 化学式: C₃₄H₄₉NO₆
• 分子量: 567.766
• InChiKey: VZWKZTYOLVODKK-REUIKQAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3E,4R)-(+)-[(1S)-(-)-bornyl] 3-[2-(-)-bornyloxy-2-oxoethylidene]-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 (1R,3S,3E,4S)-(+)-7-tert-butoxycarbonyl-2-(2'-acetoxyethylidene)-3-acetoxymethyl-7-azabicyclo[2.2.1]hept-5-ene
  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：

  (R)-(-)-[bis-(1S)-(-)-bornyl] 2,3-pentadienedioate 、 1-吡咯甲酸叔丁酯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以94%的产率得到(1S,2S,3E,4R)-(+)-[(1S)-(-)-bornyl] 3-[2-(-)-bornyloxy-2-oxoethylidene]-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
  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.