Benzoic acid 5-methyl-tetrahydro-furan-2-yl ester | 173392-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid 5-methyl-tetrahydro-furan-2-yl ester
• 英文别名: 5-Methyltetrahydrofuran-2-yl benzoate；(5-methyloxolan-2-yl) benzoate
• CAS: 173392-27-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: TWDAKVMAEJPLEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  Benzoic acid 5-methyl-tetrahydro-furan-2-yl ester 在 palladium diacetate 、 正丁基锂 、 cerium(III) chloride 、 camphor-10-sulfonic acid 、 叔丁基锂 、 二异丙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， -78.0~180.0 ℃ 、4.0 kPa 条件下， 反应 114.0h， 生成 (2R,5S)-2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-7-en-6-ol
  参考文献：
  名称：

  Concise Synthesis of cis- and trans-Theaspirones via Oxonium Ion-Initiated Pinacol Ring Expansion

  摘要：

  The odoriferous principle of black tea has been produced from 2,2-dimethylcyclopentanone. The reaction sequence begins with 1,2-addition of 5-lithio-2-methyl-2,3-dihydrofuran to this ketone and immediate acid-catalyzed ring expansion of the resulting carbinols to a separable pair of spiro ethers. Individual conversion of these diastereomers to a,P-unsaturated ketones is followed by tandem condensation with the methyllithium-lithium bromide complex and oxidation with pyridinium chlorochromate.

  DOI：

  10.1021/jo951890h
• 作为产物：
  描述：

  5-甲基四氢呋喃-2-醇 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到Benzoic acid 5-methyl-tetrahydro-furan-2-yl ester
  参考文献：
  名称：

  Concise Synthesis of cis- and trans-Theaspirones via Oxonium Ion-Initiated Pinacol Ring Expansion

  摘要：

  The odoriferous principle of black tea has been produced from 2,2-dimethylcyclopentanone. The reaction sequence begins with 1,2-addition of 5-lithio-2-methyl-2,3-dihydrofuran to this ketone and immediate acid-catalyzed ring expansion of the resulting carbinols to a separable pair of spiro ethers. Individual conversion of these diastereomers to a,P-unsaturated ketones is followed by tandem condensation with the methyllithium-lithium bromide complex and oxidation with pyridinium chlorochromate.

  DOI：

  10.1021/jo951890h

文献信息

• Concise Synthesis of <i>cis</i>- and <i>trans</i>-Theaspirones via Oxonium Ion-Initiated Pinacol Ring Expansion
  作者：Leo A. Paquette、James C. Lanter、Hui-Ling Wang

  DOI：10.1021/jo951890h

  日期：1996.1.1

  The odoriferous principle of black tea has been produced from 2,2-dimethylcyclopentanone. The reaction sequence begins with 1,2-addition of 5-lithio-2-methyl-2,3-dihydrofuran to this ketone and immediate acid-catalyzed ring expansion of the resulting carbinols to a separable pair of spiro ethers. Individual conversion of these diastereomers to a,P-unsaturated ketones is followed by tandem condensation with the methyllithium-lithium bromide complex and oxidation with pyridinium chlorochromate.