methyl (1R,4aR,5R,8aR)-5-(tert-butyldimethylsilyloxy)-4a-methyl-2-oxo-decahydronaphthalene-1-carboxylate | 1402170-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,4aR,5R,8aR)-5-(tert-butyldimethylsilyloxy)-4a-methyl-2-oxo-decahydronaphthalene-1-carboxylate
• 英文别名: methyl (1R,4aR,5R,8aR)-5-[tert-butyl(dimethyl)silyl]oxy-4a-methyl-2-oxo-1,3,4,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
• CAS: 1402170-93-7
• 化学式: C₁₉H₃₄O₄Si
• 分子量: 354.562
• InChiKey: PYFXRSJOBQCNBB-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  methyl (1R,4aR,5R,8aR)-5-(tert-butyldimethylsilyloxy)-4a-methyl-2-oxo-decahydronaphthalene-1-carboxylate 在 咪唑 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 potassium methanolate 、 四丁基氟化铵 、 氨 、 lithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (3S,4aR,6aR,7R,10aR,10bS)-3,10b-ethano-3-methoxy-4,4,6a-trimethyl-3,4,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-1H-naphto[1,2-c]pyran-7-ol
  参考文献：
  名称：

  First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii

  摘要：

  The first synthesis of (+)-decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii, was accomplished by starting from (R)-(-)-Wieland-Miescher ketone, in which our original spiro-cyclization reaction was featured as a key step. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.067
• 作为产物：
  描述：

  氰基甲酸甲酯 、 (8S^*, 8aS^*)-8-tert-butyldimethylsilyloxy-8a-methyl-1,5,6,7,8,8a-hexahydronaphthalen-3(2H)-one 在 氨 、 lithium 、 叔丁醇 、 天然橡胶 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以78%的产率得到methyl (1R,4aR,5R,8aR)-5-(tert-butyldimethylsilyloxy)-4a-methyl-2-oxo-decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii

  摘要：

  The first synthesis of (+)-decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii, was accomplished by starting from (R)-(-)-Wieland-Miescher ketone, in which our original spiro-cyclization reaction was featured as a key step. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.067

文献信息

• First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii
  作者：Kimiharu Nakazaki、Kojiro Hayashi、Shintaro Hosoe、Takuya Tashiro、Masaki Kuse、Hirosato Takikawa

  DOI：10.1016/j.tet.2012.08.067

  日期：2012.11

  The first synthesis of (+)-decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii, was accomplished by starting from (R)-(-)-Wieland-Miescher ketone, in which our original spiro-cyclization reaction was featured as a key step. (C) 2012 Elsevier Ltd. All rights reserved.