(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2R,3S)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester | 215228-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2R,3S)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester
• CAS: 215228-28-7
• 化学式: C₃₀H₃₂O₉
• 分子量: 536.579
• InChiKey: OGSBJDXNYQOSFD-SIGFBIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2R,3S)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 2.5h， 生成 (-)-(7'E,7R,8S)-3,4,5'-trimethoxy-4',7-epoxy-8,3'-neolign-7'-ene-9,9'-diol
  参考文献：
  名称：

  On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton

  摘要：

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00725-x
• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86.5%的产率得到(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2R,3S)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester
  参考文献：
  名称：

  On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton

  摘要：

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00725-x