(3R,3aR,7R,7aR)-7-Methoxymethoxy-3-methyl-7a-(2-oxo-propyl)-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one | 160714-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (3R,3aR,7R,7aR)-7-Methoxymethoxy-3-methyl-7a-(2-oxo-propyl)-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one
• 英文别名: (3R,3aR,7R,7aR)-7-(methoxymethoxy)-3-methyl-7a-(2-oxopropyl)-3,3a,4,7-tetrahydro-2-benzofuran-1-one
• CAS: 160714-23-8
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: DDSCEAPQNVXSGB-GFQSEFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,3aR,7R,7aR)-7-Methoxymethoxy-3-methyl-7a-(2-oxo-propyl)-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,4R,5R,8R,9R,11R)-9-Hydroxy-11-methoxymethoxy-4,9-dimethyl-3-oxa-tricyclo[6.2.1.0^1,5]undecan-2-one 、 (1S,4R,5R,8R,9S,11R)-9-Hydroxy-11-methoxymethoxy-4,9-dimethyl-3-oxa-tricyclo[6.2.1.0^1,5]undecan-2-one
  参考文献：
  名称：

  Total Synthesis of (-)-Grayanotoxin III

  摘要：

  Total synthesis of(-)-grayanotoxin III (3), a unique tetracyclic diterpene isolated from the leaves of various plants of the family Ericaceae, has been successfully accomplished featuring the highly stereoselective cyclization reactions induced by SmI2.

  DOI：

  10.1021/jo00098a009
• 作为产物：
  描述：

  氯甲基甲基醚 、 (3R,3aR,7R,7aR)-7-Hydroxy-3-methyl-7a-(2-oxo-propyl)-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,3aR,7R,7aR)-7-Methoxymethoxy-3-methyl-7a-(2-oxo-propyl)-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Total Synthesis of (-)-Grayanotoxin III

  摘要：

  Total synthesis of(-)-grayanotoxin III (3), a unique tetracyclic diterpene isolated from the leaves of various plants of the family Ericaceae, has been successfully accomplished featuring the highly stereoselective cyclization reactions induced by SmI2.

  DOI：

  10.1021/jo00098a009

文献信息

• Acetoxyl Group Directed Cyclization Promoted by SmI₂:  Directing Group Determined Stereocomplementarity
  作者：Toshiyuki Kan、Seijiro Hosokawa、Shinji Nara、Hiroaki Tamiya、Haruhisa Shirahama、Fuyuhiko Matsuda

  DOI：10.1021/jo049203m

  日期：2004.12.1

  Complete reversal of diastereoselectivity was observed in the SmI2-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI2-induced ketyl-olefin coupling cyclizations of the 6-hydroxy ketone 1 and delta-acetoxy ketone 3.