crotyltri-n-butylstannane | 24850-32-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: crotyltri-n-butylstannane
• 英文别名: -triethyl-zinn；1-Triaethylstannyl-butan-(2)；Triethylstannyl-but-2-en
• CAS: 24850-32-6
• 化学式: C₁₀H₂₂Sn
• 分子量: 260.995
• InChiKey: WHCOUJYEONPNOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  三甲基锡 、 crotyltri-n-butylstannane 生成 crotyltrimethyltin
  参考文献：
  名称：

  Matarasso-Tchiroukhine, E.; Cadiot, P., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1973, vol. 276, p. 1637 - 1640

  摘要：

  DOI：
• 作为产物：
  描述：

  triethylvinylstannane 在 CHCl₃ 作用下， 以 乙醚 为溶剂， 生成 crotyltri-n-butylstannane
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.2.4, page 181 - 192

  摘要：

  DOI：

文献信息

• Anomalous threo-diastereoselectivity in allylic silane- or stannane–aldehyde condensation reactions: new interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations
  作者：Koichi Mikami、Kazuya Kawamoto、Teck-Peng Loh、Takeshi Nakai

  DOI：10.1039/c39900001161

  日期：——

  Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.

  在螯合条件下，β-取代的巴豆基硅烷或锡烷与2-苄氧基丙醛的分子间反应中观察到了不寻常的苏-非对映选择性，这表明对苯二酚的偏爱于反平面的过渡态。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.4, 1.2.1.1.2.4.2, page 22 - 31
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.1.8, page 69 - 93
  作者：

  DOI：——

  日期：——
• Albert, H. J.; Neumann, W. P.; Ritter, H. P., Liebigs Annalen der Chemie, 1970, vol. 737, p. 152 - 157
  作者：Albert, H. J.、Neumann, W. P.、Ritter, H. P.

  DOI：——

  日期：——
• 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.