3-Furan-2-yl-3-hydroxy-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester | 372947-65-4

• 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: 3-Furan-2-yl-3-hydroxy-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS: 372947-65-4
• 化学式: C₃₀H₃₄O₄
• 分子量: 458.598
• InChiKey: KYNODKBAOJVAPU-NAXNZMNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Furan-2-yl-3-hydroxy-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 在 potassium hydrogensulfate 作用下， 以 xylene 为溶剂， 反应 1.5h， 以64%的产率得到[(1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (E)-3-(furan-2-yl)prop-2-enoate
  参考文献：
  名称：

  Stereoselective Hydrocoupling of [(1R)-exo]-3-exo-(Diphenylmethyl)bornyl Cinnamates by Electroreduction

  摘要：

  [GRAPHICS]The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, synthesized from (1R)-(+)-camphor in three steps, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.

  DOI：

  10.1021/ol016566p
• 作为产物：
  描述：

  (+)-camphor trimethylsilyl enol ether 在 lithium aluminium tetrahydride 、 四氯化钛 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-Furan-2-yl-3-hydroxy-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Stereoselective Hydrocoupling of [(1R)-exo]-3-exo-(Diphenylmethyl)bornyl Cinnamates by Electroreduction

  摘要：

  [GRAPHICS]The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, synthesized from (1R)-(+)-camphor in three steps, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.

  DOI：

  10.1021/ol016566p