(1S,3S,8S)-3-(1-Hydroxy-1-methyl-ethyl)-8-isobutyryl-9,9-dimethyl-4-oxa-tricyclo[6.3.1.0^1,5]dodecane-7,12-dione | 1025840-07-6

• 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: (1S,3S,8S)-3-(1-Hydroxy-1-methyl-ethyl)-8-isobutyryl-9,9-dimethyl-4-oxa-tricyclo[6.3.1.0^1,5]dodecane-7,12-dione
• 英文别名: (1S,3S,8S)-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(2-methylpropanoyl)-4-oxatricyclo[6.3.1.01,5]dodecane-7,12-dione
• CAS: 1025840-07-6
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: XFRMHQFJQJAEIW-MYUJHIMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3S,8S)-3-(1-Hydroxy-1-methyl-ethyl)-8-isobutyryl-9,9-dimethyl-4-oxa-tricyclo[6.3.1.0^1,5]dodecane-7,12-dione 在 sodium tetrachloropalladate(II) 叔丁基过氧化氢 、 ammonium cerium(IV) nitrate 、 碘 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 生成 (1S,3S,8S)-3-(1-Hydroxy-1-methyl-ethyl)-6-iodo-8-isobutyryl-9,9-dimethyl-4-oxa-tricyclo[6.3.1.0^1,5]dodec-5-ene-7,12-dione
  参考文献：
  名称：

  Studies toward the total synthesis of garsubellin A: synthesis of 8-deprenyl-garsubellin A

  摘要：

  During studies directed toward the total synthesis of garsubellin A, synthesis of 8-deprenyl-garsubellin A, containing three (of four in the natural product) stereocenters with the proper configurations, was achieved. Key steps are a one-pot lactone formation, a formal migration to the bicyclo[3.3.1]nonane-1,3,5-trione, and an intramolecular Wacker-type tetrahydrofuran formation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00650-0
• 作为产物：
  描述：

  (1R,5S)-5-((S)-5,5-Dimethyl-2-oxo-[1,3]dioxolan-4-ylmethyl)-1-isobutyryl-8,8-dimethyl-bicyclo[3.3.1]non-3-ene-2,9-dione 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,3S,8S)-3-(1-Hydroxy-1-methyl-ethyl)-8-isobutyryl-9,9-dimethyl-4-oxa-tricyclo[6.3.1.0^1,5]dodecane-7,12-dione
  参考文献：
  名称：

  Studies toward the total synthesis of garsubellin A: synthesis of 8-deprenyl-garsubellin A

  摘要：

  During studies directed toward the total synthesis of garsubellin A, synthesis of 8-deprenyl-garsubellin A, containing three (of four in the natural product) stereocenters with the proper configurations, was achieved. Key steps are a one-pot lactone formation, a formal migration to the bicyclo[3.3.1]nonane-1,3,5-trione, and an intramolecular Wacker-type tetrahydrofuran formation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00650-0