3,4-didehydro-3-deoxo-dihydro-O-acetylisophotosantonic lactone | 17946-92-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,4-didehydro-3-deoxo-dihydro-O-acetylisophotosantonic lactone
• 英文别名: [(3S,3aS,6R,6aR,9aR,9bS)-3,6,9-trimethyl-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-6-yl] acetate
• CAS: 17946-92-8
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: COXANKFYXJHAEW-RWRJGHIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-didehydro-3-deoxo-dihydro-O-acetylisophotosantonic lactone 在 吡啶 、 氢氧化钾 、 三氟甲磺酸酐 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.05h， 生成 isocostus lactone
  参考文献：
  名称：

  Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

  摘要：

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10392-1
• 作为产物：
  描述：

  在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以52%的产率得到3,4-didehydro-3-deoxo-dihydro-O-acetylisophotosantonic lactone
  参考文献：
  名称：

  Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

  摘要：

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10392-1

文献信息

• A Biomimetic Total Synthesis of (+)-Ainsliadimer A
  作者：Chao Li、Xueliang Yu、Xiaoguang Lei

  DOI：10.1021/ol101705j

  日期：2010.10.1

  A protecting group free and biomimetic total synthesis of (+)-ainsliadimer A has been accomplished in 14 steps from a-santonin. The synthesis relies on a hydrogen bonding promoted [4 + 2]-hetero-Diels-Alder dimerization to afford the key homodimer intermediate, which demonstrates the feasibility of using nonenzymatic conditions to achieve the proposed biosynthesis.
• Configurations of alcohols obtained from dihydro- O -acetylisophoto-α-santonic lactone
  作者：B Garcı́a Marrero

  DOI：10.1016/s0040-4020(00)01133-9

  日期：2001.2