(3aR,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-3a-hydroxy-3,4,5,6,7,7a-hexahydro-1-benzofuran-2-one | 433218-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-3a-hydroxy-3,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
• CAS: 433218-95-2
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: FRXGKEIOMFNBMA-UHIISALHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-3a-hydroxy-3,4,5,6,7,7a-hexahydro-1-benzofuran-2-one 在 氢氟酸 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (4R,6S)-2-Dihydroaquilegiolide
  参考文献：
  名称：

  A synthesis of cyclohexanoid butenolides isolated from Sinomenium acutum

  摘要：

  Starting from an enantiopure building-block serving as the chiral equivalent of 4-hydroxycyclohexa-2.5-dien-1-one, a diastereocontrolled synthesis of four cyclohexanoid butenolides has been investigated. The inherent convex-face selectivity exerted by the chiral building block was a key aspect of this method which afforded three of the five known butenolides, with only one losing its original chiral integrity during the conversion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02319-x
• 作为产物：
  描述：

  (3aR,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-3a-trimethylsilyloxy-3,4,5,6,7,7a-hexahydro-1-benzofuran-2-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(3aR,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-3a-hydroxy-3,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
  参考文献：
  名称：

  A synthesis of cyclohexanoid butenolides isolated from Sinomenium acutum

  摘要：

  Starting from an enantiopure building-block serving as the chiral equivalent of 4-hydroxycyclohexa-2.5-dien-1-one, a diastereocontrolled synthesis of four cyclohexanoid butenolides has been investigated. The inherent convex-face selectivity exerted by the chiral building block was a key aspect of this method which afforded three of the five known butenolides, with only one losing its original chiral integrity during the conversion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02319-x