methyl 2-[14-(methyl 12-methoxypodocarpa-8,11,13-trien-19-oate)]ethanoate | 287919-45-3

• 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: methyl 2-[14-(methyl 12-methoxypodocarpa-8,11,13-trien-19-oate)]ethanoate
• CAS: 287919-45-3
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: QMLYCVXCWQRWRW-QIJUGHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[14-(methyl 12-methoxypodocarpa-8,11,13-trien-19-oate)]ethanoate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以60%的产率得到methyl 2-[14-(methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate)]ethanoate
  参考文献：
  名称：

  Functionalisation of Alkylalkoxysilanes. Studies Towards Annulations of Diterpenoids

  摘要：

  Ortho-(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H2O2. Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH3. BMS, H2O2, Et3SiH/CF3COOH, TBAF) without isolation of intermediate products (oxasilepin, diol, trifluoroacetate). Use of the 14-(2-diethoxysilylmethyl) analogue improved the overall yield significantly (75 versus 40%). Re-oxidation of ring B with CAN gave the Delta(5)-7-oxo derivative, which was converted into an enone-aldehyde by treatment with Collins' reagent. The conjugated alkene was reduced stereoselectively with SmI2, which, however, did not promote pinacol coupling of the resulting 1,5-keto aldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00302-1
• 作为产物：
  描述：

  methyl 14-(2-diethoxymethylsilylethyl)-12-methoxy-7-oxo-podocarpa-8,11,13-trien-19-oate 在 chromium(VI) oxide 、 三甲基氯硅烷 作用下， 以 丙酮 为溶剂， 反应 23.0h， 生成 methyl 2-[14-(methyl 12-methoxypodocarpa-8,11,13-trien-19-oate)]ethanoate
  参考文献：
  名称：

  Functionalisation of Alkylalkoxysilanes. Studies Towards Annulations of Diterpenoids

  摘要：

  Ortho-(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H2O2. Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH3. BMS, H2O2, Et3SiH/CF3COOH, TBAF) without isolation of intermediate products (oxasilepin, diol, trifluoroacetate). Use of the 14-(2-diethoxysilylmethyl) analogue improved the overall yield significantly (75 versus 40%). Re-oxidation of ring B with CAN gave the Delta(5)-7-oxo derivative, which was converted into an enone-aldehyde by treatment with Collins' reagent. The conjugated alkene was reduced stereoselectively with SmI2, which, however, did not promote pinacol coupling of the resulting 1,5-keto aldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00302-1