trimethyl((Z)-1,2-diphenylvinyl)stannane | 91574-96-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trimethyl((Z)-1,2-diphenylvinyl)stannane
• 英文别名: (Z)-(trimethylstannyl)stilbene；1-Trimethylstannyl-1,2-diphenylethene；1,2-diphenylethenyl(trimethyl)stannane
• CAS: 91574-96-8
• 化学式: C₁₇H₂₀Sn
• 分子量: 343.056
• InChiKey: RMACQYUIZZMFCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trimethyl((Z)-1,2-diphenylvinyl)stannane 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以80%的产率得到反式-1,2-二苯乙烯
  参考文献：
  名称：

  Stereospecific stille-coupling reaction of (Z)-1,2-bis(trimethylstannyll)ethenes with hypervalent iodonium salts

  摘要：

  The Stille coupling of (Z)-1,2-bis(trimethylstannyl)ethenes with hypervalent iodonium salts (1 equiv) proceeded stereospecifically in the presence of PdCl2 (5 mol %) in DMF at room temperature to afford partially substituted (Z)-vinylstannanes under mild conditions. Alternatively, the use of 2 equivalents of hypervalent iodonium salts afforded tri-substituted alkenes. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00575-4
• 作为产物：
  描述：

  三甲基锡 、 二苯基乙炔 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到trimethyl((Z)-1,2-diphenylvinyl)stannane
  参考文献：
  名称：

  苯基取代的乙烯基锡烷：亲电取代反应中的合成和反应性。

  摘要：

  Seven phenyl-substituted vinylstannanes have been prepared. (Z)-beta-(trimethylstannyl)styrene, alpha-(trimethylstannyl)styrene, and 1,1-diphenyl-2-(trimethylstannyl)ethene were prepared by Grignard coupling between the appropriate phenyl-substituted vinyl bromide and chlorotrimethylstannane. (E)-beta-(Trimethylstannyl)styrene and (Z)-(trimethylstannyl)stilbene were prepared by AIBN catalyzed hydrostannation of the appropriate phenyl-substituted acetylene. (E)-(Trimethylstannyl)stilbene and methyl (E)-2-(trimethylstannyl)cinnamate were prepared by palladium(0) catalyzed hydrostannation of diphenylacetylene and methyl phenylpropiolate, respectively. Each compound was characterized by H-1, C-13, and Sn-119 NMR. Reactivity of each compound to protodestannylation was determined by spectrophotometric or H-1 NMR measurement of second order rate constants. The relative reactivity is interpreted on the basis of the electronic and steric effects of the phenyl substituents. The stereochemistry of destannylation resulted in retention of configuration for four of the compounds, consistent with an S(E)2 mechanism. However, methyl (E)-2-(trimethylstannyl)cinnamate gave an E/Z product ratio of essentially. This result is consistent with an allenol mechanism for protodestannylation of this compound.

  DOI：

  10.1021/om00015a031

文献信息

• Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes
  作者：H. Yoshida、A. Shinke、Y. Kawano、K. Takaki

  DOI：10.1039/c5cc02720a

  日期：——

  A universal system for highly α-selective hydrostannylation of terminal alkynes has been developed by use of a distannane or a silylstannane as a stannylating reagent under copper catalysis.

  已经开发出一种通用系统，通过在铜催化下使用二锡烷或硅基锡烷作为锡化试剂，实现对末端炔烃的高度α选择性氢基锡化。
• Photochemical properties of cis- and trans-1,2-diphenylethenyl-trimethyltin(IV) and cis-1,2-diphenylpropenyltrimethyltin(IV) : organometallic derivatives of stilbene
  作者：John M. Kelly、Raymond J. Trautman

  DOI：10.1039/dt9840000909

  日期：——

  Upon direct u.v. irradiation in cyclohexane, benzene, alcohol, or chloroform solution, [Sn(CPhCHPh)Me3](1) undergoes cis-trans isomerization about the olefin double bond as the only efficient reaction. No evidence has been found for either homolytic or heterolytic photocleavage of the Sn–C bond as a primary process. Unusually for stilbenes the photostationary state reached on irradiation (313 nm) is

  在环己烷，苯，醇或氯仿溶液中直接紫外线照射后，[Sn（CPh CHPh）Me 3 ]（1）绕烯烃双键进行顺-反异构化是唯一有效的反应。没有证据表明Sn–C键的均相或异相光解是一个主要过程。通常，对于斯蒂芬苯胺，在辐射（313 nm）处达到的光平稳状态富含反式异构体（在环己烷中，顺式：反式的比例为27：73），因为顺式的吸收系数更高在该波长下的异构体。来自有机敏化剂的能量转移后，也可能引起异构化。对于[Sn（CPh CMePh）Me 3 ]（2）也观察到了相似的结果。
• Cis-Trans stereoselectivity in the Stannylmetallation of Diphenylacetylene
  作者：Clark H. Cummins、Eva J. Gordon

  DOI：10.1016/0040-4039(94)88263-0

  日期：1994.10

  Stereospecific cis- or trans- stannylcupration of diphenylacetylene can be obtained by temperature control during vinylcuprate hydrolysis.

  可以通过在乙烯基铜酸盐水解过程中进行温度控制来获得二苯基乙炔的立体特异性顺式或反式苯乙烯基转移。
• Sequential Reactions of Trimethylstannyl Anions with Vinyl Chlorides and Dichlorides by the S_RN1 Mechanism Followed by Palladium-Catalyzed Cross-Coupling Processes
  作者：Eduardo F. Córsico、Roberto A. Rossi

  DOI：10.1021/jo049287z

  日期：2004.9.1

  good yields of vinylstannanes. Some of them react in the dark, and others need light stimulation to react. The fact that these reactions are inhibited by radical and radical anion traps shows that they occur by the SRN1 mechanism. When the reaction takes place with 1,1-dichloro-1-alkenes, monosubstitution reduced products are formed in an E/Z mixture. The efficient synthesis of triarylolefins by Pd(0)-catalyzed

  三甲基甲锡离子（Me中反应3的Sn - ）与在液氨氯乙烯得到乙烯基锡烷的良好产率。它们中的一些在黑暗中反应，而另一些则需要光刺激来反应。这些反应受到自由基和自由基阴离子阱的抑制，这一事实表明它们是通过S RN 1机理发生的。当与1,1-二氯-1-烯烃进行反应时，在E / Z混合物中形成单取代的还原产物。报道了通过乙烯基锡与多种碘代芳烃的Pd（0）催化的交叉偶联反应有效合成三芳基烯烃。在一锅式反应中获得了相似的产率。
• Phenyl-Substituted Vinylstannanes: Synthesis and Reactivity in Electrophilic Substitution Reactions
  作者：John C. Cochran、Harmony K. Phillips、Samson Tom、Alexander R. Hurd、Brian S. Bronk

  DOI：10.1021/om00015a031

  日期：1994.3

  Seven phenyl-substituted vinylstannanes have been prepared. (Z)-beta-(trimethylstannyl)styrene, alpha-(trimethylstannyl)styrene, and 1,1-diphenyl-2-(trimethylstannyl)ethene were prepared by Grignard coupling between the appropriate phenyl-substituted vinyl bromide and chlorotrimethylstannane. (E)-beta-(Trimethylstannyl)styrene and (Z)-(trimethylstannyl)stilbene were prepared by AIBN catalyzed hydrostannation of the appropriate phenyl-substituted acetylene. (E)-(Trimethylstannyl)stilbene and methyl (E)-2-(trimethylstannyl)cinnamate were prepared by palladium(0) catalyzed hydrostannation of diphenylacetylene and methyl phenylpropiolate, respectively. Each compound was characterized by H-1, C-13, and Sn-119 NMR. Reactivity of each compound to protodestannylation was determined by spectrophotometric or H-1 NMR measurement of second order rate constants. The relative reactivity is interpreted on the basis of the electronic and steric effects of the phenyl substituents. The stereochemistry of destannylation resulted in retention of configuration for four of the compounds, consistent with an S(E)2 mechanism. However, methyl (E)-2-(trimethylstannyl)cinnamate gave an E/Z product ratio of essentially. This result is consistent with an allenol mechanism for protodestannylation of this compound.