α,α-dimethyl-(5-phenylthio)-2-furfuryl propargyl ether | 220326-43-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: α,α-dimethyl-(5-phenylthio)-2-furfuryl propargyl ether
• CAS: 220326-43-2
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: UMPBVRLZMXDUPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  α,α-dimethyl-(5-phenylthio)-2-furfuryl propargyl ether 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 以41%的产率得到1,1-dimethyl-3-phenylthio-5-hydroxy-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers Followed by Phenylthio and Trialkylsilyl Groups Rearrangement

  摘要：

  AbstractA new reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a‐c with t‐BuOK in t‐BuOH at 85 ° C gave the phenylthio group rearrangement products 5a‐c and 6a‐c. A reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.

  DOI：

  10.1002/jccs.199800119
• 作为产物：
  描述：

  二苯二硫醚 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 3-溴丙炔 作用下， 反应 8.0h， 生成 α,α-dimethyl-(5-phenylthio)-2-furfuryl propargyl ether
  参考文献：
  名称：

  Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers Followed by Phenylthio and Trialkylsilyl Groups Rearrangement

  摘要：

  AbstractA new reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a‐c with t‐BuOK in t‐BuOH at 85 ° C gave the phenylthio group rearrangement products 5a‐c and 6a‐c. A reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.

  DOI：

  10.1002/jccs.199800119

文献信息

• Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers Followed by Phenylthio and Trialkylsilyl Groups Rearrangement
  作者：Chi-Te Chuang、Chia-Hui Yen、Hsien-Jen Wu

  DOI：10.1002/jccs.199800119

  日期：1998.12

  AbstractA new reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a‐c with t‐BuOK in t‐BuOH at 85 ° C gave the phenylthio group rearrangement products 5a‐c and 6a‐c. A reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.