methyl 13-acetyl-12-(((1,1-dimethylethyl)dimethylsilyl)oxy)podocarpa-8,11,13-trien-19-oate | 173612-84-5

• 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 13-acetyl-12-(((1,1-dimethylethyl)dimethylsilyl)oxy)podocarpa-8,11,13-trien-19-oate
• 英文别名: methyl (1S,4aS,10aR)-7-acetyl-6-[tert-butyl(dimethyl)silyl]oxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 173612-84-5
• 化学式: C₂₆H₄₀O₄Si
• 分子量: 444.687
• InChiKey: PJVLSYBMPZAGEH-RCXJIHSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烯基三乙氧基硅烷 、 methyl 13-acetyl-12-(((1,1-dimethylethyl)dimethylsilyl)oxy)podocarpa-8,11,13-trien-19-oate 在 RuH₂(CO)(PPh₃)₃ 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以98%的产率得到methyl 13-acetyl-14-[2-(triethoxysilyl)ethyl]-12-{[(1,1-dimethylethyl)dimethylsilyl]oxy}podocarpa-8,11,13-trien-19-oate
  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
• 作为产物：
  描述：

  methyl 13-acetyl-12-hydroxypodocarpa-8,11,13-trien-19-oate 、 叔丁基二甲基氯硅烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 5.0h， 以96%的产率得到methyl 13-acetyl-12-(((1,1-dimethylethyl)dimethylsilyl)oxy)podocarpa-8,11,13-trien-19-oate
  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

文献信息

• Ruthenium-catalysed ortho vinylation of aromatic ketones with alkynes; unexpected cyclopentaannulation
  作者：Paul W.R Harris、Clifton E.F Rickard、Paul D Woodgate

  DOI：10.1016/s0022-328x(99)00400-3

  日期：1999.11

  Ruthenium-catalysed coupling of aromatic ketones with alkynylsilanes yielded in most cases ortho vinylation adducts in high yield. The predominant stereochemistry of the newly introduced double bond was E in all but a few cases. In contrast, 1-acetylnaphthalene underwent a one-pot insertion-cyclisation sequence yielding cyclopenta[a]naphthalene derivatives. A bis acetylene gave both mono and bis insertion products. (C) 1999 Elsevier Science S.A. All rights reserved.