(3S,4aR,6aR,7R,10aR,10bS)-3,10b-ethano-3-methoxy-4,4,6a,7,8-pentamethyl-3,4,4a,5,6,6a,7,10,10a,10b-decahydro-1H-naphto[1,2-c]pyran-7-ol | 1402171-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3S,4aR,6aR,7R,10aR,10bS)-3,10b-ethano-3-methoxy-4,4,6a,7,8-pentamethyl-3,4,4a,5,6,6a,7,10,10a,10b-decahydro-1H-naphto[1,2-c]pyran-7-ol
• 英文别名: (1S,2R,6R,7R,10R,12S)-12-methoxy-5,6,7,11,11-pentamethyl-13-oxatetracyclo[10.2.2.01,10.02,7]hexadec-4-en-6-ol
• CAS: 1402171-04-3
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: RPLPKDHPUBINPO-IQBUSDBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4aR,6aR,7R,10aR,10bS)-3,10b-ethano-3-methoxy-4,4,6a,7,8-pentamethyl-3,4,4a,5,6,6a,7,10,10a,10b-decahydro-1H-naphto[1,2-c]pyran-7-ol 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(3S,4aR,6aR,7S,8S,9S,10aR,10bS)-8,9-epoxy-3,10b-ethano-3-methoxy-4,4,6a,7,8-pentamethyl-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：

  (3S,4aR,6aR,10aR,10bR)-3,10b-ethano-3-methoxy-4,4,6a,8-tetramethyl-3,4,4a,5,6,6a,10a,10b-octahydro-1H-naphto[1,2-c]pyran-7(10H)-one 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.33h， 以98%的产率得到(3S,4aR,6aR,7R,10aR,10bS)-3,10b-ethano-3-methoxy-4,4,6a,7,8-pentamethyl-3,4,4a,5,6,6a,7,10,10a,10b-decahydro-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

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.