(3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-tetrahydropyranyloxy-4a,5-dimethyl-2(3H)-naphthalenone | 241813-89-8

• 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: (3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-tetrahydropyranyloxy-4a,5-dimethyl-2(3H)-naphthalenone
• 英文别名: (3R,4aR,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-4a,5-dimethyl-3-(oxan-2-yloxy)-3,4,5,6-tetrahydronaphthalen-2-one
• CAS: 241813-89-8
• 化学式: C₂₃H₃₈O₄Si
• 分子量: 406.638
• InChiKey: BLQFNMDDXQZHKM-KWYOMSSMSA-N

物化性质

• 沸点：
  481.906±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.042±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-tetrahydropyranyloxy-4a,5-dimethyl-2(3H)-naphthalenone 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 (1R,2S,7R,8aR)-1,2,6,7,8,8a-hexahydro-1,8a-dimethyl-6-oxo-7-tetrahydropyranyloxynaphthalen-2-yl (2E,4E,6S)-6-methyl-2,4-octadienoate
  参考文献：
  名称：

  Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

  摘要：

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00407-x
• 作为产物：
  描述：

  (4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-4a,5-dimethyl-2(3H)-naphthalenone 在 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.83h， 生成 (3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-tetrahydropyranyloxy-4a,5-dimethyl-2(3H)-naphthalenone
  参考文献：
  名称：

  Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

  摘要：

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00407-x