(3aRS,7aSR)-7a-methyl-3a,4,7,7a-tetrahydro-isobenzofuranon | 14679-34-6

• 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: (3aRS,7aSR)-7a-methyl-3a,4,7,7a-tetrahydro-isobenzofuranon
• 英文别名: (3aR,7aS)-7a-methyl-3,3a,4,7-tetrahydro-2-benzofuran-1-one
• CAS: 14679-34-6；119817-98-0；119818-00-7
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: XEXFYJPWTYCCKQ-CBAPKCEASA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  266.8±39.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aRS,7aSR)-7a-methyl-3a,4,7,7a-tetrahydro-isobenzofuranon 在 potassium permanganate 、 magnesium sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以64%的产率得到(3aRS,5RS,6SR,7aSR)-5,6-dihydroxy-7a-methyl-perhydro-isobenzofuranon
  参考文献：
  名称：

  Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen

  摘要：

  Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88%) and 7 a (4%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by H-1-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.

  DOI：

  10.1007/bf00809359
• 作为产物：
  描述：

  (1R,6S)-6-(methoxycarbonyl)-6-methylcyclohex-3-ene-1-carboxylic acid 生成 (3aRS,7aSR)-7a-methyl-3a,4,7,7a-tetrahydro-isobenzofuranon
  参考文献：
  名称：

  Efficient stereocontrol of a quaternary chiral center in the cyclohexene systems. Potential chiral synthons for vitamin D and related compounds by enzymatic approach

  摘要：

  DOI：

  10.1016/s0040-4039(00)88487-7

文献信息

• SHIMADA, MITSUYUKI;KOBAYASHI, SUSUMU;OHNO, MASAJI, TETRAHEDRON LETT., 29,(1988) N 52, C. 6961-6964
  作者：SHIMADA, MITSUYUKI、KOBAYASHI, SUSUMU、OHNO, MASAJI

  DOI：——

  日期：——
• Efficient stereocontrol of a quaternary chiral center in the cyclohexene systems. Potential chiral synthons for vitamin D and related compounds by enzymatic approach
  作者：Mitsuyuki Shimada、Susumu Kobayashi、Masaji Ohno

  DOI：10.1016/s0040-4039(00)88487-7

  日期：——
• Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen
  作者：Roswitha Stejskal、Ernst Urban、Horst V�llenkle

  DOI：10.1007/bf00809359

  日期：1991.3

  Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88%) and 7 a (4%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by H-1-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.