4-Phenacylspiro[1,3-oxathiine-2,2'-adamantane]-6-one | 1018858-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Phenacylspiro[1,3-oxathiine-2,2'-adamantane]-6-one
• 英文别名: 4-phenacylspiro[1,3-oxathiine-2,2'-adamantane]-6-one
• CAS: 1018858-73-5
• 化学式: C₂₁H₂₂O₃S
• 分子量: 354.47
• InChiKey: HMQYNROPIFGFPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Phenacylspiro[1,3-oxathiine-2,2'-adamantane]-6-one 220.0 ℃ 、6.67 kPa 条件下， 以62%的产率得到4-mercapto-6-phenyl-2-pyrone
  参考文献：
  名称：

  Reaction of 1,3-Oxathiin-6-ones with Bases: Synthesis of 4-Mercapto-2-pyrone

  摘要：

  The reaction of 4-aryl-1,3-oxathiin-6-one 3,3-dioxide 3c with secondary amine gave cinnamamides 6 and ammonium sulfinates 7. On the other hand, the reaction of 4-methyl-1,3-oxathiin-6-one 1b with LDA, followed by the addition of benzoyl chloride, gave corresponding phenacyldioxenone 8a and 5-benzoyl-4-methyl-1,3-thiodioxenone 9 in nearly 1:1 ratio, whereas the reaction with 1-benzoyl-1,2,3-benzotriazole gave only 8a in 78% yield. Thermolysis of 8a gave the corresponding 4-mercapto-2-pyrone 4a in 62% yield.

  DOI：

  10.3987/com-07-11236
• 作为产物：
  描述：

  1-苯甲酰-1H-苯并三唑 、 4'-methylspiro[adamantane-2,2'-6H'-[1,3]-oxathiin]-6'-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以0.276 g的产率得到4-Phenacylspiro[1,3-oxathiine-2,2'-adamantane]-6-one
  参考文献：
  名称：

  Reaction of 1,3-Oxathiin-6-ones with Bases: Synthesis of 4-Mercapto-2-pyrone

  摘要：

  The reaction of 4-aryl-1,3-oxathiin-6-one 3,3-dioxide 3c with secondary amine gave cinnamamides 6 and ammonium sulfinates 7. On the other hand, the reaction of 4-methyl-1,3-oxathiin-6-one 1b with LDA, followed by the addition of benzoyl chloride, gave corresponding phenacyldioxenone 8a and 5-benzoyl-4-methyl-1,3-thiodioxenone 9 in nearly 1:1 ratio, whereas the reaction with 1-benzoyl-1,2,3-benzotriazole gave only 8a in 78% yield. Thermolysis of 8a gave the corresponding 4-mercapto-2-pyrone 4a in 62% yield.

  DOI：

  10.3987/com-07-11236

文献信息

• Reaction of 1,3-Oxathiin-6-ones with Bases: Synthesis of 4-Mercapto-2-pyrone
  作者：Kentaro Okuma、Masahiro Koda

  DOI：10.3987/com-07-11236

  日期：——

  The reaction of 4-aryl-1,3-oxathiin-6-one 3,3-dioxide 3c with secondary amine gave cinnamamides 6 and ammonium sulfinates 7. On the other hand, the reaction of 4-methyl-1,3-oxathiin-6-one 1b with LDA, followed by the addition of benzoyl chloride, gave corresponding phenacyldioxenone 8a and 5-benzoyl-4-methyl-1,3-thiodioxenone 9 in nearly 1:1 ratio, whereas the reaction with 1-benzoyl-1,2,3-benzotriazole gave only 8a in 78% yield. Thermolysis of 8a gave the corresponding 4-mercapto-2-pyrone 4a in 62% yield.