(1S,4aR,6R,6aR,9S,11aS,11bR,12R)-1-((tert-butyldimethylsilyl)oxy)-6,12-dihydroxy-4,4,11b-trimethyl-8-methylenedodecahydro-6a,9-methanocyclohepta[a]naphthalen-7(1H)-one | 1599477-55-0

• 英文名称: (1S,4aR,6R,6aR,9S,11aS,11bR,12R)-1-((tert-butyldimethylsilyl)oxy)-6,12-dihydroxy-4,4,11b-trimethyl-8-methylenedodecahydro-6a,9-methanocyclohepta[a]naphthalen-7(1H)-one
• CAS: 1599477-55-0
• 化学式: C₂₆H₄₄O₄Si
• 分子量: 448.718
• InChiKey: PQFMYXKBGJWVLY-FQRXOEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,4aR,6R,6aR,9S,11aS,11bR,12R)-1-((tert-butyldimethylsilyl)oxy)-6,12-dihydroxy-4,4,11b-trimethyl-8-methylenedodecahydro-6a,9-methanocyclohepta[a]naphthalen-7(1H)-one 在 三苯基膦 、 偶氮二甲酸二乙酯 、 对硝基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以19%的产率得到(3aR,5aR,9S,9aR,9bR,11aS)-9-[tert-butyl(dimethyl)silyl]oxy-6,6,9a-trimethyl-1-methylidene-3a,5,5a,7,8,9,9b,10,11,11a-decahydronaphtho[1,2-g][1]benzofuran-2-one
  参考文献：
  名称：

  Efficient transformation of 7,14-dihydroxy-ent-kaurenes to novel ent-abietanes having cis-fused α-methylene γ-lactones under Mitsunobu reaction conditions and their cytotoxicities

  摘要：

  Transformation of plant-origin 7,14-dihydroxy-ent-kaurenes to ent-abietanes having a cis-fused alpha-methylene gamma-lactones was accomplished efficiently under the Mitsunobu reaction conditions. The yields of the desired products were apparently influenced by the steric hindrance at C-1. The cytotoxic activity on P388 murine leukemia cells of the ent-abietanes having cis-fused alpha-methylene gamma-lactones produced were assayed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.082
• 作为产物：
  描述：

  (1R,2R,6R,8R,12S,13R,14S,17S)-12-hydroxy-4,4,9,9,13-pentamethyl-18-methylidene-3,5-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecan-19-one 在 2,6-二甲基吡啶 、 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1S,4aR,6R,6aR,9S,11aS,11bR,12R)-1-((tert-butyldimethylsilyl)oxy)-6,12-dihydroxy-4,4,11b-trimethyl-8-methylenedodecahydro-6a,9-methanocyclohepta[a]naphthalen-7(1H)-one
  参考文献：
  名称：

  Efficient transformation of 7,14-dihydroxy-ent-kaurenes to novel ent-abietanes having cis-fused α-methylene γ-lactones under Mitsunobu reaction conditions and their cytotoxicities

  摘要：

  Transformation of plant-origin 7,14-dihydroxy-ent-kaurenes to ent-abietanes having a cis-fused alpha-methylene gamma-lactones was accomplished efficiently under the Mitsunobu reaction conditions. The yields of the desired products were apparently influenced by the steric hindrance at C-1. The cytotoxic activity on P388 murine leukemia cells of the ent-abietanes having cis-fused alpha-methylene gamma-lactones produced were assayed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.082