(Z)-1,2-bis(p-tolylthio)-1-octene | 137540-56-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-1,2-bis(p-tolylthio)-1-octene
• 英文别名: (Z)-1,2-bis(4-methylphenylthio)-1-octene；(Z)-1,2-bis[(4-methylphenyl)thio]oct-1-ene；(Z)-oct-1-ene-1,2-diylbis(p-tolylsulfane)；1-methyl-4-[(Z)-1-(4-methylphenyl)sulfanyloct-1-en-2-yl]sulfanylbenzene
• CAS: 137540-56-8
• 化学式: C₂₂H₂₈S₂
• 分子量: 356.596
• InChiKey: FFLNPGINHJSPLI-XLNRJJMWSA-N

物化性质

• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-1,3-bis<(p-methylphenyl)thio>-2-nonen-1-one 在 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 反应 3.0h， 以95%的产率得到(Z)-1,2-bis(p-tolylthio)-1-octene
  参考文献：
  名称：

  “β-顺式SAr效应”对α，β-不饱和酰基和芳酰基复合物的脱羰作用。

  摘要：

  位于α，β-不饱和酰基和芳酰基的10个金属配合物中β-顺式位置的一对杂原子孤立地大大促进了化学计量和催化脱羰反应。

  DOI：

  10.1039/b515616e

文献信息

• Stereoselective Synthesis of (Z)-1,2-Dithio-1-alkenes via Copper-Catalyzed Thiolation of (Z)-2-Bromovinyl Sulfides
  作者：Wanzhi Chen、Huayue Wu、Hui Xu、Jiuxi Chen

  DOI：10.1055/s-0031-1290067

  日期：2012.2

  We describe a new method for the stereoselective synthesis of (Z)-1,2-dithio-1-alkenes via copper-catalyzed cross-coupling of (Z)-2-bromovinyl sulfides and thiols. The desired products are obtained in good to excellent yields. The double bond geometry of the starting (Z)-2-bromovinyl sulfides is retained under these reaction conditions.

  我们描述了一种通过铜催化的(Z)-2-溴乙烯硫化物和硫醇的交叉耦合反应来实现(Z)-1,2-二硫-1-烯烃的立体选择性合成的新方法。所需的产物以良好至优秀的产率获得。在这种反应条件下，起始的(Z)-2-溴乙烯硫化物的双键几何结构得以保留。
• Rhodium-Catalyzed Regio- and Stereoselective 1-Seleno-2-thiolation of 1-Alkynes
  作者：Mieko Arisawa、Yoshihiro Kozuki、Masahiko Yamaguchi

  DOI：10.1021/jo034990t

  日期：2003.11.1

  RhH(PPh(3))(4) and 1,1'-bis(diphenylphosphino)ferrocene catalyze the regio- and stereoselective additions of diaryl disulfides and diaryl diselenides to 1-alkynes giving (Z)-1-arylseleno-2-arylthio-1-alkenes. The catalyst promotes the addition reaction of dibutyl disulfide and dibutyl diselenide to 1-octyne with a similar selectivity giving (Z)-1-butylseleno-2-butylthio-1-octene but with a lower catalytic

  铑配合物RhH（PPh（3））（4）和1,1'-双（二苯基膦基）二茂铁催化二芳基二硫化物和二芳基二硒化物向1-炔烃的区域和立体选择性加成反应，生成（Z）-1-芳基硒代2 -芳硫基-1-烯烃。该催化剂以相似的选择性促进二丁基二硫化物和二丁基二硒化物向1-辛炔的加成反应，得到（Z）-1-丁基硒代-2-丁基硫基-1-辛烯，但催化活性较低。当在RhH（PPh（3））（4）和1,4-二苯基膦基丁烷存在下使用过量的二丁基二硫化物对二丁基二硒化物时，可以更高的产率获得相同的产品。
• Addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex
  作者：Jianying Li、Jun Liu、Mingzhong Cai

  DOI：10.3184/030823409x12526892025829

  日期：2009.10

  2-bis(arylthio)-substituted alkenes have been conveniently synthesised in high yields by the stereoselective addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex. This polymeric palladium catalyst can be recovered and reused many times without any loss of activity.

  通过在 MCM-41 负载的双齿膦钯 (0) 配合物催化下，二芳基二硫化物立体选择性加成到末端炔烃上，可以方便地以高产率合成各种 (Z)-1,2-双(芳硫基)-取代的烯烃. 这种聚合钯催化剂可以回收和重复使用多次而不会损失任何活性。
• 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.
• Addition Reaction of Dialkyl Disulfides to Terminal Alkynes Catalyzed by a Rhodium Complex and Trifluoromethanesulfonic Acid
  作者：Mieko Arisawa、Masahiko Yamaguchi

  DOI：10.1021/ol015521l

  日期：2001.3.1

  [GRAPHICS]Addition of dialkyl disulfides to terminal alkynes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (Z)-bis(alkylthio)olefins stereoselectively.