(3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-hydroxy-4a,5-dimethyl-2(3H)-naphthalenone | 241813-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-hydroxy-4a,5-dimethyl-2(3H)-naphthalenone
• 英文别名: (3R,4aR,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4a,5-dimethyl-3,4,5,6-tetrahydronaphthalen-2-one
• CAS: 241813-86-5
• 化学式: C₁₈H₃₀O₃Si
• 分子量: 322.52
• InChiKey: FTBUDVYWLOWTAM-OBZJAWTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-hydroxy-4a,5-dimethyl-2(3H)-naphthalenone 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 (3R,4aR,5R,6S)-4,4a,5,6-tetrahydro-6-hydroxy-4a,5-dimethyl-3-tetrahydropyranyloxy-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
• 作为产物：
  描述：

  3-(三甲基硅烷基)-3-丁烯-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 碘代三甲硅烷 、 甲基锂 、 sodium methylate 、 lithium carbonate 、 双(三甲基硅烷基)氨基钾 、 苯甲酸酐 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 六甲基二硅氮烷 、 lithium bromide 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.67h， 生成 (3R,4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6-tetrahydro-3-hydroxy-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