(3aS,7aS,4'R,5'R)-3a-hydroxy-4',5'-diphenyl-3,3a,7,7a-tetrahydrospiro[benzofuro-6(2H),2'-[1,3]dioxolan]-2-one | 443923-80-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3aS,7aS,4'R,5'R)-3a-hydroxy-4',5'-diphenyl-3,3a,7,7a-tetrahydrospiro[benzofuro-6(2H),2'-[1,3]dioxolan]-2-one
• 英文别名: (3'aS,4R,5R,7'aS)-3'a-hydroxy-4,5-diphenylspiro[1,3-dioxolane-2,6'-7,7a-dihydro-3H-1-benzofuran]-2'-one
• CAS: 443923-80-6
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: GVQGFJWJOFIMIX-OYNPSCLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,7aS,4'R,5'R)-3a-hydroxy-4',5'-diphenyl-3,3a,7,7a-tetrahydrospiro[benzofuro-6(2H),2'-[1,3]dioxolan]-2-one 在 吡啶 、 氯化亚砜 、 montmorillonite K-10 作用下， 以 二氯甲烷 为溶剂， 反应 144.5h， 生成 联苯乙醛
  参考文献：
  名称：

  From p-benzoquinone to cyclohexane chirons: first asymmetric synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide

  摘要：

  Starting from a common, easily available, enantiopure monoketal of p-benzoquinone, the synthesis of a large number of cyclohexane chirons has been achieved. The first synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide has been performed from one of these new building blocks. The wide variety of functional groups of this series of chirons makes them useful for subsequent synthetic processes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00357-4
• 作为产物：
  描述：

  4,4-<(1R,2R)-1,2-(diphenyl)ethylenedioxi>-2,5-cyclohexadienone 在 indium 、 氢氧化钾 、 三氟乙酸 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.58h， 生成 (3aS,7aS,4'R,5'R)-3a-hydroxy-4',5'-diphenyl-3,3a,7,7a-tetrahydrospiro[benzofuro-6(2H),2'-[1,3]dioxolan]-2-one
  参考文献：
  名称：

  From p-benzoquinone to cyclohexane chirons: first asymmetric synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide

  摘要：

  Starting from a common, easily available, enantiopure monoketal of p-benzoquinone, the synthesis of a large number of cyclohexane chirons has been achieved. The first synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide has been performed from one of these new building blocks. The wide variety of functional groups of this series of chirons makes them useful for subsequent synthetic processes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00357-4

文献信息

• First synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide
  作者：Mariona Cantó、Pedro de March、Marta Figueredo、Josep Font、Sonia Rodrı́guez、Angel Álvarez-Larena、Juan F. Piniella

  DOI：10.1016/s0957-4166(02)00119-2

  日期：2002.4

  The benzofuranone natural products (+)-rengyolone and (+)- and (-)-menisdaurilide have been synthesised for the first time from a common enantiopure cyclohexane building block derived from a monoketal of p-benzoquinone. (C) 2002 Elsevier Science Ltd. All rights reserved.