Acetic acid (2S,3R,4R)-4-(benzo[1,3]dioxole-5-carbonyl)-2-benzo[1,3]dioxol-5-yl-tetrahydro-furan-3-ylmethyl ester | 218607-89-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: Acetic acid (2S,3R,4R)-4-(benzo[1,3]dioxole-5-carbonyl)-2-benzo[1,3]dioxol-5-yl-tetrahydro-furan-3-ylmethyl ester
• 英文别名: [(2S,3R,4R)-4-(1,3-benzodioxole-5-carbonyl)-2-(1,3-benzodioxol-5-yl)oxolan-3-yl]methyl acetate
• CAS: 218607-89-7
• 化学式: C₂₂H₂₀O₈
• 分子量: 412.396
• InChiKey: OGQZBCSKJFMTEM-PONJGIIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R)-4-(benzo[1,3]dioxole-5-carbonyl)-2-benzo[1,3]dioxol-5-yl-tetrahydro-furan-3-ylmethyl ester 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以66%的产率得到Acetic acid (2R,3R)-2-(benzo[1,3]dioxole-5-carbonyl)-4-benzo[1,3]dioxol-5-yl-3-hydroxymethyl-4-oxo-butyl ester
  参考文献：
  名称：

  Selective oxidation of lignan compounds by dimethyldioxirane. Diastereoselective opening of asarinin furo-furan skeleton

  摘要：

  Asarinin, a furo-furan lignan compound with two benzyl-ethereal carbons of opposite stereochemistry, was monooxidised at a selected centre by DMD to a chiral substituted tetrahydrofuran. Use of a dilute solution of DMD was crucial for the success of the process. The stereochemistry of the product was confirmed by a similar oxidation of sesamin, the C-7' isomer of asarinin (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01912-1
• 作为产物：
  描述：

  乙酸酐 、 细辛脂素 在 吡啶 、 二甲基二环氧乙烷 作用下， 以80%的产率得到Acetic acid (2S,3R,4R)-4-(benzo[1,3]dioxole-5-carbonyl)-2-benzo[1,3]dioxol-5-yl-tetrahydro-furan-3-ylmethyl ester
  参考文献：
  名称：

  Selective oxidation of lignan compounds by dimethyldioxirane. Diastereoselective opening of asarinin furo-furan skeleton

  摘要：

  Asarinin, a furo-furan lignan compound with two benzyl-ethereal carbons of opposite stereochemistry, was monooxidised at a selected centre by DMD to a chiral substituted tetrahydrofuran. Use of a dilute solution of DMD was crucial for the success of the process. The stereochemistry of the product was confirmed by a similar oxidation of sesamin, the C-7' isomer of asarinin (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01912-1