cyclohex-2-en-1-yltriphenylstannane | 14540-08-0

• 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: cyclohex-2-en-1-yltriphenylstannane
• 英文别名: 1-Triphenylstannyl-cyclohexen-(2)；cyclohex-2-enyltriphenylstannane；[(1R)-cyclohex-2-en-1-yl]-triphenylstannane
• CAS: 14540-08-0
• 化学式: C₂₄H₂₄Sn
• 分子量: 431.165
• InChiKey: UWTODOFVTZWURF-UHFFFAOYSA-N

物化性质

• 熔点：
  81.5-83 °C(Solv: ethanol (64-17-5); benzene (71-43-2))
• 沸点：
  473.5±48.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  二氧化硫 、 cyclohex-2-en-1-yltriphenylstannane 以 氯仿 为溶剂， 生成 triphenylstannyl cyclohex-2-enylsulfinate
  参考文献：
  名称：

  Young, David; Kitching, William, Organometallics, 1988, vol. 7, # 5, p. 1196 - 1201

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴环己烯 生成 cyclohex-2-en-1-yltriphenylstannane
  参考文献：
  名称：

  FISH R. H.; BROLINE B. M., J. ORGANOMETAL. CHEM., 1978, 159, NO 3, 255-278

  摘要：

  DOI：

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。
• 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.4, 1.2.1.1.7.4.2, page 73 - 77
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.15.5, page 396 - 401
  作者：

  DOI：——

  日期：——
• Cai, Jiaqiang; Davies, Alwyn G., Journal of the Chemical Society. Perkin transactions II, 1992, # 10, p. 1743 - 1746
  作者：Cai, Jiaqiang、Davies, Alwyn G.

  DOI：——

  日期：——