3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-hydroxy-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester | 620945-74-6

• 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: 3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-hydroxy-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester
• CAS: 620945-74-6
• 化学式: C₄₀H₅₀O₁₀
• 分子量: 690.831
• InChiKey: HQAPUJCSOLZAIU-IVINUJDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  129.98
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-hydroxy-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester 以72%的产率得到[(1R,2R,3S,4R)-3-[(1R,2S,3R,4R)-3-[3-(1,3-benzodioxol-5-yl)-3-oxopropanoyl]oxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 3-(1,3-benzodioxol-5-yl)-3-oxopropanoate
  参考文献：
  名称：

  Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br2

  摘要：

  The oxidative coupling of diaroylacetate derivatives prepared from (1R, 1'R)-exo,exo'-3,3'-biisoborneol with NaH-Br-2 gave the corresponding intramolecularly coupled products stereoselectively. The major (R,R)-isomers thus obtained were transformed to (-)-Sesamin and (-)-Eudesmin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00572-x
• 作为产物：
  描述：

  (1R,1'R)-exo,exo'-3,3'-biisoborneol 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-hydroxy-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester
  参考文献：
  名称：

  Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br2

  摘要：

  The oxidative coupling of diaroylacetate derivatives prepared from (1R, 1'R)-exo,exo'-3,3'-biisoborneol with NaH-Br-2 gave the corresponding intramolecularly coupled products stereoselectively. The major (R,R)-isomers thus obtained were transformed to (-)-Sesamin and (-)-Eudesmin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00572-x