1-phenylthio-4-(2-tetrahydropyranyloxy)-2-pentyne | 184674-08-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenylthio-4-(2-tetrahydropyranyloxy)-2-pentyne
• 英文别名: 2H-Pyran, tetrahydro-2-[1-[3-(phenylthio)-1-propynyl]ethoxy]-；2-(5-phenylsulfanylpent-3-yn-2-yloxy)oxane
• CAS: 184674-08-6
• 化学式: C₁₆H₂₀O₂S
• 分子量: 276.4
• InChiKey: TUBABDHBGVZCAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenylthio-4-(2-tetrahydropyranyloxy)-2-pentyne 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (Z)-1-(Phenylthio)pent-3-en-1-yne 、 [((E)-Pent-3-en-1-ynyl)sulfanyl]-benzene
  参考文献：
  名称：

  Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor

  摘要：

  4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01380-1

文献信息

• Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor
  作者：Atsushi Ogawa、Kazunari Sakagami、Akiko Shima、Hitoshi Suzuki、Satsuki Komiya、Yoshinori Katano、Oyo Mitsunobu

  DOI：10.1016/s0040-4039(02)01380-1

  日期：2002.9

  4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes. (C) 2002 Elsevier Science Ltd. All rights reserved.