(3aR,7aR)-2-methoxy-3,3a,4,7a-tetrahydro-2H-1-benzofuran-5-one | 1225205-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3aR,7aR)-2-methoxy-3,3a,4,7a-tetrahydro-2H-1-benzofuran-5-one
• CAS: 1225205-26-4
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: UGBAQELHCRUUSG-ICIOHDDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,7aR)-2-methoxy-3,3a,4,7a-tetrahydro-2H-1-benzofuran-5-one 、 肉桂酰氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(3aR,4Z,7aS)-2-hydroxy-4-[(E)-1-hydroxy-3-phenylprop-2-enylidene]-2,3,3a,7a-tetrahydro-1-benzofuran-5-one
  参考文献：
  名称：

  The first asymmetric total syntheses of both enantiomers of cryptocaryone

  摘要：

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.101
• 作为产物：
  描述：

  甲醇 、 (3aR,7aR)-2-hydroxy-3,3a,4,7a-tetrahydro-2H-1-benzofuran-5-one 以 水 、 乙腈 为溶剂， 生成 (3aR,7aR)-2-methoxy-3,3a,4,7a-tetrahydro-2H-1-benzofuran-5-one
  参考文献：
  名称：

  The first asymmetric total syntheses of both enantiomers of cryptocaryone

  摘要：

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.101

文献信息

• The first asymmetric total syntheses of both enantiomers of cryptocaryone
  作者：Hiromichi Fujioka、Kenji Nakahara、Tomohiro Oki、Kie Hirano、Tatsuya Hayashi、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2010.01.101

  日期：2010.4

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.