3-(1',3'-benzodioxol-5'-ylmethyl)-2,3-dihydrobenzo[e]1,4-oxathiepin-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(1',3'-benzodioxol-5'-ylmethyl)-2,3-dihydrobenzo[e]1,4-oxathiepin-5-one
• 英文别名: 3-(1,3-Benzodioxol-5-ylmethyl)-2,3-dihydro-4,1-benzoxathiepin-5-one
• 化学式: C₁₇H₁₄O₄S
• 分子量: 314.362
• InChiKey: VJNPEBWWWHGORD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  黄樟素氧化物 、 硫代水杨酸 以85%的产率得到3-(1',3'-benzodioxol-5'-ylmethyl)-2,3-dihydrobenzo[e]1,4-oxathiepin-5-one
  参考文献：
  名称：

  One-Pot Synthesis of Benzo[e]1,4-oxathiepin-5-ones under Solvent-Free Condition via Self-Promoted Thiolysis of 1,2-Epoxides

  摘要：

  Under solvent-free conditions, thiosalicylic acid (2) efficiently self-promotes the thiolysis of 1,2-epoxides 1, anti-stereoselectively and generally totally beta-regioselectively. The resulting beta-hydroxysulfide products 3 have been obtained in very good yields. Benzo[e]1,4-oxathiepin-5-ones 4 have been easily prepared in a regio- and diasteroselective manner and in satisfactory yields under SFC by a one-pot protocol including nucleophilic ring opening of 1,2-epoxides 1 by thiosalicylic acid (2) and thermally induced lactonization of beta-hydroxy arylsulfides 3. Solvent-free condition and the absence of any catalyst make this procedure atom-economical and environmentally friendly.

  DOI：

  10.1021/jo0487496

文献信息

• One-Pot Synthesis of Benzo[<i>e</i>]1,4-oxathiepin-5-ones under Solvent-Free Condition via Self-Promoted Thiolysis of 1,2-Epoxides
  作者：Francesco Fringuelli、Ferdinando Pizzo、Simone Tortoioli、Luigi Vaccaro

  DOI：10.1021/jo0487496

  日期：2004.12.1

  Under solvent-free conditions, thiosalicylic acid (2) efficiently self-promotes the thiolysis of 1,2-epoxides 1, anti-stereoselectively and generally totally beta-regioselectively. The resulting beta-hydroxysulfide products 3 have been obtained in very good yields. Benzo[e]1,4-oxathiepin-5-ones 4 have been easily prepared in a regio- and diasteroselective manner and in satisfactory yields under SFC by a one-pot protocol including nucleophilic ring opening of 1,2-epoxides 1 by thiosalicylic acid (2) and thermally induced lactonization of beta-hydroxy arylsulfides 3. Solvent-free condition and the absence of any catalyst make this procedure atom-economical and environmentally friendly.