(Z)-1,3-Bis(phenylthio)-2-nonen-1-one | 137540-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: (Z)-1,3-Bis(phenylthio)-2-nonen-1-one
• 英文别名: S-phenyl (Z)-3-phenylsulfanylnon-2-enethioate
• CAS: 137540-48-8
• 化学式: C₂₁H₂₄OS₂
• 分子量: 356.553
• InChiKey: XQTHEWWCUHIXLO-JZJYNLBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1,3-Bis(phenylthio)-2-nonen-1-one 在 四(三苯基膦)钯 三正丁基氢锡 作用下， 以 苯 为溶剂， 以89%的产率得到3-phenylthio-2-nonenal
  参考文献：
  名称：

  Chemoselective conversion of thioesters to aldehydes: Palladium-catalyzed reduction of (Z)-1,3-Bis(arylthio)-2-alken-1-ones with n-Bu3SnH

  摘要：

  (Z)-1,3-Bis(arylthio)-2-alken-1-ones (1) are chemoselectively reduced to the corresponding aldehydes (3) by n-Bu3SnH with the aid of palladium catalysts under the very mild reaction conditions.

  DOI：

  10.1016/s0040-4039(00)60449-5
• 作为产物：
  描述：

  1-辛炔 、 一氧化碳 、 二苯二硫醚 在 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 80.0 ℃ 、5.88 MPa 条件下， 反应 39.0h， 以5%的产率得到(Z)-1,2-bis(phenylthio)-1-octene
  参考文献：
  名称：

  Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes

  摘要：

  Novel transition-metal-catalyzed reactions of disulfides and diselenides with acetylenes are described. In the of tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4], the (1) of diaryl disulfides and diselenides to terminal acetylenes 1 takes place stereoselectively to give high yields of (Z)-1,2-bis(arylthio)-1-alkenes 2 and (Z)-1,2-bis(arylseleno)-1-alkenes 3, respectively. A mechanistic proposal includes the following: (1) oxidative addition of (ArY)2 [Y = S, Se] to low-valent palladium species, (2) stereoselective cis-thiopalladation or cis-selenopalladation to acetylenes to form a cis-vinylpalladium intermediate, and (3) reductive elimination of the product with retention of the stereochemistry. When the reaction of diaryl disulfides and diselenides with terminal acetylenes is performed under the pressure of carbon monoxide, the carbonylative addition occurs to afford (Z)-1,3-bis(arylthio)-2-alken-1-ones 4 and (Z)-1,3-bis(arylseleno)-2-alken-1-ones 5, respectively. Carbon monoxide is regioselectively incorporated on the side of the terminal carbon of the acetylenes.

  DOI：

  10.1021/ja00026a013

文献信息

• Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes
  作者：Hitoshi Kuniyasu、Akiya Ogawa、Shinichiro Miyazaki、Ilhyong Ryu、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1021/ja00026a013

  日期：1991.12

  Novel transition-metal-catalyzed reactions of disulfides and diselenides with acetylenes are described. In the of tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4], the (1) of diaryl disulfides and diselenides to terminal acetylenes 1 takes place stereoselectively to give high yields of (Z)-1,2-bis(arylthio)-1-alkenes 2 and (Z)-1,2-bis(arylseleno)-1-alkenes 3, respectively. A mechanistic proposal includes the following: (1) oxidative addition of (ArY)2 [Y = S, Se] to low-valent palladium species, (2) stereoselective cis-thiopalladation or cis-selenopalladation to acetylenes to form a cis-vinylpalladium intermediate, and (3) reductive elimination of the product with retention of the stereochemistry. When the reaction of diaryl disulfides and diselenides with terminal acetylenes is performed under the pressure of carbon monoxide, the carbonylative addition occurs to afford (Z)-1,3-bis(arylthio)-2-alken-1-ones 4 and (Z)-1,3-bis(arylseleno)-2-alken-1-ones 5, respectively. Carbon monoxide is regioselectively incorporated on the side of the terminal carbon of the acetylenes.
• Chemoselective conversion of thioesters to aldehydes: Palladium-catalyzed reduction of (Z)-1,3-Bis(arylthio)-2-alken-1-ones with n-Bu3SnH
  作者：Hitoshi Kuniyasu、Akiya Ogawa、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)60449-5

  日期：1993.4

  (Z)-1,3-Bis(arylthio)-2-alken-1-ones (1) are chemoselectively reduced to the corresponding aldehydes (3) by n-Bu3SnH with the aid of palladium catalysts under the very mild reaction conditions.