3-(phenoxymethyl)-2,3-dihydro-5H-benzo[e]1,4-oxathiepin-5-one | 821768-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(phenoxymethyl)-2,3-dihydro-5H-benzo[e]1,4-oxathiepin-5-one
• 英文别名: 5H-4,1-Benzoxathiepin-5-one, 2,3-dihydro-3-(phenoxymethyl)-；3-(phenoxymethyl)-2,3-dihydro-4,1-benzoxathiepin-5-one
• CAS: 821768-60-9
• 化学式: C₁₆H₁₄O₃S
• 分子量: 286.351
• InChiKey: JQHFSCZJCXPWIR-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  480.7±38.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[2'-(carboxy)phenylthio]-1-phenoxypropan-2-ol 反应 1.0h， 以96%的产率得到3-(phenoxymethyl)-2,3-dihydro-5H-benzo[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

• Advancing the Development of Recyclable Aromatic Polyesters by Functionalization and Stereocomplexation
  作者：Hua‐Zhong Fan、Xing Yang、Jia‐Hao Chen、Yi‐Min Tu、Zhongzheng Cai、Jian‐Bo Zhu

  DOI：10.1002/anie.202117639

  日期：2022.4.4

  The exploitation of epoxides as building blocks enabled the preparation of a series of recyclable aromatic polyesters with functionalizable moieties, which has driven a wide array of post-polymerization modifications toward access of value-added materials. Stereocomplexed polymers were formed with enhanced thermal stability and crystallinity, and random copolymers displayed polyolefin-like mechanical

  使用环氧化物作为结构单元能够制备一系列具有功能化部分的可回收芳族聚酯，这推动了广泛的聚合后改性以获取增值材料。立体络合聚合物的形成具有增强的热稳定性和结晶度，无规共聚物表现出类似聚烯烃的机械性能。
• 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.