(3R,3aR,7aS)-3-methoxy-5,6-dimethyl-3a,4,7,7a-tetrahydro-3H-2-benzofuran-1-one | 139344-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: (3R,3aR,7aS)-3-methoxy-5,6-dimethyl-3a,4,7,7a-tetrahydro-3H-2-benzofuran-1-one
• CAS: 139344-31-3
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: LRFJJRDCOOEUPY-IQJOONFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 <3R-<3α(1R,2S,5R),3aα,7aα>>-3a,4,7,7a-tetrahydro-5,6-dimethyl-3-<<5-methyl-2-(1-methylethyl)cyclohexyl>oxy>-1(3H)-isobenzofuranone 在 对甲苯磺酸 作用下， 反应 2.0h， 生成 (3R,3aR,7aS)-3-methoxy-5,6-dimethyl-3a,4,7,7a-tetrahydro-3H-2-benzofuran-1-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with 5-menthyloxy-2-(5H)-furanone

  摘要：

  A new class of chiral dienophiles, 5-alkoxy-2(5H)-furanones, has been developed. Both enantiomers of 5-menthyloxy-2(5H)-furanone are readily available in enantiomerically pure form, starting from furfural and d- or l-menthol. Excellent diastereoselectivities (d.e. greater-than-or-equal-to 99%) are obtained in thermal Diels-Alder reactions with several cyclic and acyclic dienes. The use of silyl dienol ethers has resulted in new routes to enantiomerically pure cyclohexanones in a highly regioselective manner.

  DOI：

  10.1016/s0957-4166(00)80024-5

文献信息

• Asymmetric Diels-Alder reactions with 5-menthyloxy-2-(5H)-furanone
  作者：Johannes C. de Jong、Fré van Bolhuis、Ben L. Feringa

  DOI：10.1016/s0957-4166(00)80024-5

  日期：1991.1

  A new class of chiral dienophiles, 5-alkoxy-2(5H)-furanones, has been developed. Both enantiomers of 5-menthyloxy-2(5H)-furanone are readily available in enantiomerically pure form, starting from furfural and d- or l-menthol. Excellent diastereoselectivities (d.e. greater-than-or-equal-to 99%) are obtained in thermal Diels-Alder reactions with several cyclic and acyclic dienes. The use of silyl dienol ethers has resulted in new routes to enantiomerically pure cyclohexanones in a highly regioselective manner.