5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one | 1007393-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one
• 英文别名: 3-Methylsulfanyl-5-propan-2-ylcyclohepta[b]furan-2-one；3-methylsulfanyl-5-propan-2-ylcyclohepta[b]furan-2-one
• CAS: 1007393-94-3
• 化学式: C₁₃H₁₄O₂S
• 分子量: 234.319
• InChiKey: CIDNZTXALMPXTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one 在 间氯过氧苯甲酸 作用下， 以35%的产率得到3-Methylsulfinyl-5-propan-2-ylcyclohepta[b]furan-2-one
  参考文献：
  名称：

  A Novel Approach to 5,5’-Diisopropyl-3,3’-bi-2H-cyclohepta[b]furan-2-one

  摘要：

  5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonate (2), which was treated with E(t)3N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf2O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one (7), thermally.

  DOI：

  10.3987/com-07-s(u)43
• 作为产物：
  描述：

  dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonate 在 三乙胺 作用下， 生成 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one
  参考文献：
  名称：

  A Novel Approach to 5,5’-Diisopropyl-3,3’-bi-2H-cyclohepta[b]furan-2-one

  摘要：

  5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonate (2), which was treated with E(t)3N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf2O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one (7), thermally.

  DOI：

  10.3987/com-07-s(u)43

文献信息

• A Novel Approach to 5,5’-Diisopropyl-3,3’-bi-2H-cyclohepta[b]furan-2-one
  作者：Noboru Morita、Junya Higashi、Kazuyuki Okada、Taku Shoji、Kozo Toyota、Masataka Watanabe、Masafumi Yasunami、Shigeru Kikuchi、Shunji Ito

  DOI：10.3987/com-07-s(u)43

  日期：——

  5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonate (2), which was treated with E(t)3N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf2O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one (7), thermally.