trimethyl-β-(phenylstyryl)stannane | 76557-96-5

• 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: trimethyl-β-(phenylstyryl)stannane
• 英文别名: trimethyl(2,2-diphenylvinyl)stannane；(2,2-diphenylethenyl)trimethyltin；2,2-Diphenylethenyl(trimethyl)stannane
• CAS: 76557-96-5
• 化学式: C₁₇H₂₀Sn
• 分子量: 343.056
• InChiKey: VCJHWKYCZAMZIU-UHFFFAOYSA-N

物化性质

• 沸点：
  116-118 °C(Press: 0.2 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 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-β-(phenylstyryl)stannane 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 1,1,4,4-甲苯基-1,3-丁二烯
  参考文献：
  名称：

  New syntheses for dilithiotrimethylenemethane: an ionic energy minimum

  摘要：

  DOI：

  10.1021/jo00303a022
• 作为产物：
  描述：

  (2-溴-1-苯基乙烯基)苯 、 三甲基氯化锡 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以62%的产率得到trimethyl-β-(phenylstyryl)stannane
  参考文献：
  名称：

  Moloney, Mark G.; Pinhey, John T.; Stoermer, Martin J., Journal of the Chemical Society. Perkin transactions I

  摘要：

  DOI：

文献信息

• α-Metallated vinyl carbanionoids
  作者：T.N. Mitchell、W. Reimann

  DOI：10.1016/0022-328x(87)85002-7

  日期：1987.3

  The influence of intramolecular coordination and solvent effects on the formation and stability of α-stannylvinyllithium reagents RR′CC(Li)SnMe3 (R′ = H, alkyl, aryl) has been investigated; intramolecular coordination via a 5-membered ring is particularly effective. Mechanisms for the isomerisation and thermal decomposition of RR′CC(Li)SnMe3 are discussed, and multinuclear NMR data (119Sn, 13C and

  研究了分子内配位和溶剂效应对α-锡烷基乙烯基锂试剂RR'CC（Li）SnMe 3（R'= H，烷基，芳基）的形成和稳定性的影响；通过五元环的分子内配位特别有效。讨论了RR'CC（Li）SnMe 3异构化和热分解的机理，并给出了这些物质的多核NMR数据（119 Sn，13 C和1 H）。
• 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.
• Formation and rearrangement of gem-dilithiodiphenylethene
  作者：Adalbert Maercker、Benno Bös、Mohammad Taghi Hajgholipour

  DOI：10.1016/s0022-328x(98)00568-3

  日期：1998.9

  1,1-Dilithio-2,2-diphenylethene (14) is accessible through double bromine lithium exchange reaction starting from 1,1-dibromo-2,2-diphenylethene (5) with lithium metal at -110 degrees C. 14 undergoes rearrangement into (E)-1-lithio-2-(2-lithiophenyl)-2-phenylethene (13) at temperatures above -100 degrees C. The (Z)-compound 15 was formed from the (E)-compound 13 at temperatures above -25 degrees C. (C) 1998 Elsevier Science S.A. All rights reserved.
• MOLONEY, MARK G.;PINHEY, JOHN T.;STOERMER, MARTIN J., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N0, C. 2645-2655
  作者：MOLONEY, MARK G.、PINHEY, JOHN T.、STOERMER, MARTIN J.

  DOI：——

  日期：——

表征谱图