1-苯基丙-2-烯基(三苯基)锡烷 | 19752-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基丙-2-烯基(三苯基)锡烷
• 英文名称: cinnamyltriphenylstannane
• CAS: 19752-28-4
• 化学式: C₂₇H₂₄Sn
• 分子量: 467.198
• InChiKey: IZPKSSXMBMDDOP-UHFFFAOYSA-N

物化性质

• 沸点：
  530.3±53.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-苯基丙-2-烯基(三苯基)锡烷 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 三苯基氢氧化锡
  参考文献：
  名称：

  IVA元素的烯丙基衍生物的碱催化裂解。一世

  摘要：

  用分光光度法研究了硅，锗和锡的3-酚烯丙基衍生物在水介质中的碱性裂解机理，溶剂同位素和伯盐效应均与S N 2随驱逐作用对金属或准金属原子的腐蚀速率有关。碳负离子。反应产物是β-甲基苯乙烯，表明质子对碳负离子的攻击发生在3位。该反应似乎受到很大的空间作用。

  DOI：

  10.1016/s0022-328x(00)90900-8
• 作为产物：
  描述：

  (E)-肉桂基(三苯基)锡烷 在 氧气 作用下， 以 氯仿 为溶剂， 以51%的产率得到1-苯基丙-2-烯基(三苯基)锡烷
  参考文献：
  名称：

  Photochemical 1,3-stannyl rearrangement of allylic stannanes

  摘要：

  对烯丙基锡烷的光化学1,3-锡重排进行了研究。在无氧条件下，(E)-肉桂基(三苯基)锡烷在苯中未观察到光重排现象，而在有氧条件下或有有机卤化物或自由基捕获剂存在时，在同一溶剂中发生光诱导的1,3-锡迁移，形成肉桂基锡烷及其支链区域异构体、1-苯基丙-2-烯基(三苯基)锡烷的光平衡混合物，后者占主导地位。肉桂基(三烷基)锡烷及其类似物在类似的光化学条件下也得到相应的支链烯丙基锡烷。这些1,3-锡迁移通过肉桂基π-π*激发的分子内过程进行，与均裂的(肉桂基)C–Sn键断裂竞争。相比之下，巴豆基和烯丙基(三丁基)锡烷的1,3-锡迁移效率不高，但其三苯基或二丁基苯基衍生物通过锡原子上的苯基团激发发生1,3-重排，得到起始线性锡化合物和支链锡化合物的区域异构体混合物，前者占主导地位。

  DOI：

  10.1039/a707609f

文献信息

• The Stannum–Ene Reactions of Benzyne and Cyclohexyne with Superb Chemoselectivity for Cyclohexyne
  作者：Lianggui Li、Chunhui Shan、Jiarong Shi、Wensheng Li、Yu Lan、Yang Li

  DOI：10.1002/anie.202117351

  日期：2022.4.19

  The stannum–ene reactions of both benzyne and cyclohexyne were realized, which is particularly suitable for cyclohexyne with a broad substrate scope and excellent chemoselectivity.

  实现了苯炔和环己炔的锡-烯反应，特别适用于环己炔，具有广泛的底物范围和优异的化学选择性。
• Contrasting Regiochemistry in Thermal and Photochemical Allylstannations of 1,2-Naphthoquinone
  作者：Yutaka Nishigaichi、Naofumi Yoshida、Mikiya Matsuura、Akio Takuwa

  DOI：10.1246/cl.1999.803

  日期：1999.8

  1,2-Naphthoquinone with γ-substituted allyltin reagents undergoes both thermal and photochemical reactions, which show the opposite regioselectivities to each other. The both reactions are supposed to proceed via the initial 1,2-addition, which occurs at the γ-position of the allyltin in the thermal reaction and at the less hindered α-position in the photoreaction, followed by the [3,3] allylic migration.

  1,2-萘醌与γ-取代的烯丙基锡试剂会发生热反应和光化学反应，这两种反应的区域选择性正好相反。这两种反应都是通过最初的 1,2-加成反应进行的，在热反应中，加成反应发生在烯丙基锡的γ 位，而在光反应中，加成反应发生在受阻较小的α 位，随后发生[3,3] 烯丙基迁移。
• Reactions of trans-cinnamyltriethyl- and trans-cinnamyltriphenyltin with tribromoborane, preferential transfer of the cinnamyl group from tin to boron
  作者：Yoshio Tanigawa、Ichiro Moritani、Shinya Nishida

  DOI：10.1016/s0022-328x(00)81576-4

  日期：1971.4
• Wurtz-Type Reductive Coupling Reaction of Allyl Bromides and Haloorganotins in Cosolvent/H2O(NH4Cl)/Zn Media as a Route to Allylstannanes and Hexaaryldistannanes
  作者：Friederike von Gyldenfeldt、Daniele Marton、Giuseppe Tagliavini

  DOI：10.1021/om00015a025

  日期：1994.3

  Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (BU2SnCl)20 in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = alpha-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (alpha-isomer), and (ii) the subsequent isomerization of the alpha-isomer furnishing mixtures of (alpha, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the alpha-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br.-Zn.+ radical ion which is trapped by the R3SnCl reactant to form the alpha-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl.-Zn.+ radical ions with R3SnCl molecules.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.15.4, page 386 - 396
  作者：

  DOI：——

  日期：——