allyltrichlorostannane | 65317-09-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 烯丙基金属
• 英文名称: allyltrichlorostannane
• 英文别名: Trichloro(prop-2-en-1-yl)stannane；trichloro(prop-2-enyl)stannane
• CAS: 65317-09-1
• 化学式: C₃H₅Cl₃Sn
• 分子量: 266.142
• InChiKey: RCLQTMSHKBQDLK-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  allyltrichlorostannane 、 (S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone
  参考文献：
  名称：

  Asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-β-lactams via novel, highly stereoselective Baylis-Hillman and allylation reactions of enantiopure 3-oxo-2-azetidinones

  摘要：

  New asymmetric routes based on both Baylis-Hillman and allylation reactions of enantiopure 3-oxo-2-azetidinones are used for the highly stereoselective, efficient preparation of densely functionalized 3-substituted 3-hydroxy-beta-lactams. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01527-0
• 作为产物：
  描述：

  烯丙基三丁基锡 、 四氯化锡 以 neat (no solvent) 为溶剂， 以67%的产率得到allyltrichlorostannane
  参考文献：
  名称：

  Structures of Vinylstannane (Ethenylstannane) and Allylstannane (2-Propenylstannane) Determined by Gas-Phase Electron Diffraction and Quantum Chemical Calculations

  摘要：

  Vinylstannane (H2C=CHSnH3) and allylstannane (H2C=CHCH2SnH3) have been synthesized, and their structures and conformational properties have been determined by A initio and density functional theory calculations and gas electron diffraction. There is only one stable conformation of vinylstannane, where one of the Sn-H bonds is synperiplanar to the double bond. The most important structural parameter is the C(sp(2))-Sn(IV) bond length, which is r(a) = 215.1(6) pm (r(c) = 214.1(6) pm). The CCSn bond angle is 121.6(4)degrees. Uncertainties are estimated errors equal to 2.5 times the least-squares standard deviation and include uncertainty in the electron wavelength. Theoretical calculations indicate that there are two stable rotameric forms of allystannane. The C=C-C-Sn chain of atoms is synperiplanar (dihedral angle = 0 degrees) in the less stable form and anticlinal (dihedral angle approximate to 106 degrees from synperiplanar) in the more stable rotamer. Theoretical calculations predict an energy difference between the two conformations of about 10 kJ mol(-1). There is no indication of the presence of the synperiplanar conformation in the gas phase at room temperature. The final analysis was therefore carried out assuming that only the anticlinal conformer was present. The C=C-C-Sn dihedral angle was found to be 102.9(19)degrees from the synperiplanar conformer, which is the smallest value found for this angle in the C=C-C-X (X = C, Si, Ge, Sn) series of compounds. The C(sp(3)) -Sn(IV) bond length is r(a) = 218.9(8) pm (r(e) = 217.6(8) pm), and the CCSn bond angle is 110.9(6)degrees. The B3LYP calculations using the cc-pVTZ basis set for C and H and the cc-pVTZ-PP basis set for Sri reproduce the experimental r(e)(C-Sn) bond distances very well, while the MP2(FC) calculations underestimate the r(e)(C-Sn) bond distances by 3-4 pm.

  DOI：

  10.1021/om0601549

文献信息

• Efficient Preparation of Functionalized Hybrid Organic/Inorganic Wells−Dawson-type Polyoxotungstates
  作者：Sébastian Bareyt、Stergios Piligkos、Bernold Hasenknopf、Pierre Gouzerh、Emmanuel Lacôte、Serge Thorimbert、Max Malacria

  DOI：10.1021/ja050397c

  日期：2005.5.1

  Hybrid organic/inorganic Wells-Dawson polyoxotungstates have been prepared through addition of functionalized tricholorostannanes to lacunary alpha(2)- and alpha(1)-[P(2)W(17)O(61)](10-). Coupling of amines and alcohols to polyoxotungstate platforms led to new structures in good yields. Coupling of chiral amines to the previously unknown organotin-substituted alpha(1) derivatives allowed the isolation

  混合有机/无机 Wells-Dawson 聚氧钨酸盐已通过将功能化的三氯锡烷添加到缺孔 alpha(2)-和 alpha(1)-[P(2)W(17)O(61)](10-) 中制备。胺和醇与聚氧钨酸盐平台的偶联以良好的收率产生了新的结构。手性胺与以前未知的有机锡取代的 alpha(1) 衍生物的偶联允许分离非对映异构体，在某些情况下，其特征是分裂 (1) H、(13) C 和 (31) P NMR 光谱。这是 alpha(1)-Wells-Dawson 系列中一对非对映异构体的 NMR 观察的第一个例子。它为那些手性多氧钨酸盐的潜在分辨率开辟了道路。
• Disproportionation reactions within the series of coordinated monoorganostannanes
  作者：D.V. Airapetyan、V.S. Petrosyan、S.V. Gruener、K.V. Zaitsev、D.E. Arkhipov、A.A. Korlyukov

  DOI：10.1016/j.jorganchem.2013.07.005

  日期：2013.12

  organotin complexes (2a–j). These organotin complexes disproportionate into diorganostannanes and inorganic coordination compounds containing two O,O-chelated ligands (3a–c). All the complexes were characterized by multinuclear NMR spectroscopy in solution and X-ray diffraction in crystalline state (2a, 2b, 2j, 3b, 3c). It was found that disproportionation reaction proceeded only for very well dissolved

  单有机锡三氯化物（RSnCl 3，R = Ph，Vin，All，Bn和c -Pr）与2-羟基羧酸的O -TMS-酰胺的相互作用提供了许多单核和双核有机锡复合物（2a - j）。这些有机锡配合物不成比例地分解成双有机锡烷和含有两个O，O螯合的配体（3a - c）的配位无机化合物。所有配合物的特征在于溶液中的多核NMR光谱和结晶态（2a，2b，2j，3b，3c的X射线衍射）。）。已经发现歧化反应仅在加热时对浓溶液中溶解得很好的物质进行。用于歧化的倾向取决于取代基的性质和如下降低：Vin的≈烯丙基> BN>博士≈  Ç -Pr >> ALK据信，歧化反应的机理的关键步骤是一个配体交换，其中。仅在双核络合物充当中间化合物的情况下才有可能。
• Formation of an allyltin bond in η3-allyl(trichlorostannyl)palladium(II) complexes
  作者：Kazuyoshi Hirako、Yuki Miyamoto、Kiyomi Kakiuchi、Hideo Kurosawa

  DOI：10.1016/0020-1693(94)03890-2

  日期：1994.7

  Abstract Attempts were made to find conditions under which formation of the allyl-tin bond takes place efficiently starting from η 3 -allylpalladium(II) complexes containing the PdSnCl 3 bond. Addition of SnCl 2 or allylic chloride was effective in this marter, while PPh 3 and maleic anhydride, which had been known before to be good accelerators of couplings between the η 3 -allyl ligand and carbon

  摘要试图寻找条件，从含有PdSnCl3键的η3-烯丙基钯（II）络合物开始有效地形成烯丙基-锡键。SnCl 2或烯丙基氯化物的添加对这种化合物有效，而PPh 3和马来酸酐（以前被认为是η3-烯丙基配体与Pd上的碳阴离子之间偶联的良好促进剂）对烯丙基完全无效。 -SnCl 3偶联。Pd（η3 -CH 2 CMeCH 2）（苯乙烯）（SnCl 3）系列配合物中取代苯乙烯的相对配位能力表明Pd中心高度缺乏电子。鉴于上述发现，讨论了钯催化由SnCl 2和烯丙基氯形成三氯化烯丙基锡（IV）的可能反应方案。
• Remote asymmetric induction in reactions between 4- and 5-benzyloxypent-2-enyl(tributyl)stannanes and chiral imines prepared from butyl glyoxylate
  作者：David J. Hallett、Eric J. Thomas

  DOI：10.1039/c39950000657

  日期：——

  Transmetallation of 4- and 5-benzyloxypent-2-enyl(tributyl)stannanes 13 and 18 with tin(IV) chloride generates intermediate allyltin trichlorides which react with imines 9 and ent-9, prepared from butyl glyoxylate and either (R)- or (S)-1-phenylethylamine, with effective 1,5-asymmetric induction.

  4- 和 5-苄氧基戊-2-烯基（三丁基）锡 13 和 18 与氯化锡（IV）发生反金属反应，生成中间体烯丙基三氯化锡，与乙醛酸丁酯和 (R)- 或 (S)-1- 苯乙胺制备的亚胺 9 和 ent-9 发生反应，产生有效的 1,5- 不对称诱导。
• New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method
  作者：Iwao Ojima、Hong Wang、Tao Wang、Edward W. Ng

  DOI：10.1016/s0040-4039(97)10677-3

  日期：1998.2

  New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.

  通过由N -t-Boc-β-内酰胺4衍生的肟基6和甲酰恶唑啉13，已经开发出具有高对映体纯度的二肽等排体（例如，羟乙烯，二羟乙烯和羟乙胺等排体）的新型有效合成途径。