14-(2-trietoxysilylethyl)-12,19-dimethoxypodocarpa-8,11,13-trien-7-one | 190669-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 14-(2-trietoxysilylethyl)-12,19-dimethoxypodocarpa-8,11,13-trien-7-one
• CAS: 190669-21-7
• 化学式: C₂₇H₄₄O₆Si
• 分子量: 492.728
• InChiKey: WOEWMVUNPVNYBI-WYMJOSIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  14-(2-trietoxysilylethyl)-12,19-dimethoxypodocarpa-8,11,13-trien-7-one 在 potassium fluoride 、 双氧水 、 碳酸氢钠 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (1S,4aS,9S,10aR)-8-(2-Hydroxy-ethyl)-6-methoxy-1-methoxymethyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ol
  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：

  乙烯基三乙氧基硅烷 、 12,19-dimethoxypodocarpa-8,11,13-trien-7-one 在 {ruthenium(0) dicarbonyltris(triphenylphosphine)} 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以94%的产率得到14-(2-trietoxysilylethyl)-12,19-dimethoxypodocarpa-8,11,13-trien-7-one
  参考文献：
  名称：

  Ruthenium-catalysed ortho alkylation of hydroxyacetophenones; the functionalisation of ring C aromatic diterpenoids

  摘要：

  Ortho C-H bond coupling of some 2-alkoxyacetophenones with olefins catalysed by ruthenium complexes results in a high yield of the ortho alkylated product, providing that a suitable protecting group is employed. No such protection was required for a para-alkoxy group; an activating effect was also observed. Bicyclic and tricyclic analogues react similarly.

  DOI：

  10.1016/s0022-328x(96)06697-1