(7aS)-7,7A-二氢-1-苯并呋喃-2,6-二酮 | 443923-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: (7aS)-7,7A-二氢-1-苯并呋喃-2,6-二酮
• 中文别名: (3R,5R,6S,8S,9S,10R,13S,14S,17S)-17-(1-羟基乙基)-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3,6-二酚
• 英文名称: (S)-6-oxo-7,7a-dihydrobenzofuran-2(6H)-one
• 英文别名: (7aS)-7,7a-dihydro-1-benzofuran-2,6-dione
• CAS: 443923-82-8
• 化学式: C₈H₆O₃
• 分子量: 150.134
• InChiKey: QIZYUCVTAFYYEU-ZETCQYMHSA-N

物化性质

• 熔点：
  109-111 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  470.2±34.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (7aS)-7,7A-二氢-1-苯并呋喃-2,6-二酮 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以74%的产率得到(+)-menisdaurilide
  参考文献：
  名称：

  First synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00119-2
• 作为产物：
  描述：

  (7aS,4'R,5'R)-4',5'-diphenyl-7,7a-dihydrospiro[benzofuro-6(2H),2'-[1,3]dioxolan]-2-one 在 montmorillonite K-10 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 以49%的产率得到(7aS)-7,7A-二氢-1-苯并呋喃-2,6-二酮
  参考文献：
  名称：

  First synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00119-2

文献信息

• From p-benzoquinone to cyclohexane chirons: first asymmetric synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide
  作者：Felix Busqué、Mariona Cantó、Pedro de March、Marta Figueredo、Josep Font、Sonia Rodrı́guez

  DOI：10.1016/s0957-4166(03)00357-4

  日期：2003.7

  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.
• 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.