(Z)-1,2-bis(phenylseleno)-4-hydroxy-1-butene | 137540-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1,2-bis(phenylseleno)-4-hydroxy-1-butene
• 英文别名: (Z)-3,4-bis(phenylselanyl)but-3-en-1-ol
• CAS: 137540-66-0
• 化学式: C₁₆H₁₆OSe₂
• 分子量: 382.222
• InChiKey: XQEYCZJQTROIOE-SSZFMOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 3-丁炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 苯硒酚 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以95%的产率得到(Z)-1,2-bis(phenylseleno)-4-hydroxy-1-butene
  参考文献：
  名称：

  炔烃中钯催化的S–S和Se–Se键的机理研究

  摘要：

  钯催化炔烃加成的S–S和Se–Se键的机理研究表明，双核过渡金属配合物参与了催化循环。发现炔与双核过渡金属配合物的配位是反应的速率决定步骤。在研究的系统中发现了不寻常的膦配体效应，增加了加成反应的产率。开发了一种新的合成程序以使用容易获得的Pd（II）配合物进行催化反应。研究了反应范围以及S–S和Se–Se键对炔烃的反应性。S–S键加成反应产物的X射线结构显示出良好的几何形状，可能用作螯合配体。

  DOI：

  10.1016/s0022-328x(03)00795-2

文献信息

• Palladium-catalyzed activation of E-E and C-E bonds in diaryl dichalcogenides (E = S, Se) under microwave irradiation conditions
  作者：V. P. Ananikov、N. V. Orlov、I. P. Beletskaya

  DOI：10.1007/s11172-005-0292-6

  日期：2005.3

  The first example of palladium-catalyzed stereoselective addition of diphenyl disulfide and diphenyl diselenide to the triple bond of terminal alkynes under microwave irradiation conditions is described. It was found that both the element—element (E-E) and carbon—element bonds can be activated in the catalytic system studied. The products of both reactions were isolated in quantitative yields. According

  描述了在微波辐射条件下钯催化的二苯基二硫醚和二苯基二硒化物立体选择性加成到末端炔烃的三键的第一个例子。发现元素-元素（EE）和碳-元素键都可以在所研究的催化体系中被激活。两种反应的产物均以定量产率分离。根据量子化学计算，反应机制涉及 EE 键与 Pd0 的氧化加成。根据微波功率和反应条件，下一阶段是与炔烃的反应或碳元素键活化。Ph2Se2与Pd0氧化加成的产物，即双核络合物[Pd2(SePh)4(PPh32]，
• 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.
• Solvent-free palladium-catalyzed addition of diaryl dichalcogenides to alkynes
  作者：V. P. Ananikov、I. P. Beletskaya

  DOI：10.1023/b:rucb.0000035637.57608.51

  日期：2004.3

  Solvent-free palladium-catalyzed addition of diaryl disulfides and diselenides to terminal alkynes makes it possible to achieve high stereoselectivity and almost 100% yields in approximate to10 min using only 0.1 mol.% catalyst. Both Pd(PPh3)(4) and easily available Pd(OAc)(2) and PdCl2 can be used in the reaction with an excess of triphenylphosphine. The catalyst and triphenylphosphine are readily recycled for repeated use. The study of the mechanism of the solvent-free catalytic reaction indicates that the process involves binuclear palladium complexes.