2,2-di-n-Butyl-4-phenyl-1,3,2-dioxastannole | 61235-70-9

• 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: 2,2-di-n-Butyl-4-phenyl-1,3,2-dioxastannole
• 英文别名: 4-phenyl-2,2-dibutyl-1,3,2-dioxastannolane；(+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan；4-phenyl-1,3-dioxa-2-stannolane-Bu2；Bu2SnPED
• CAS: 61235-70-9
• 化学式: C₁₆H₂₆O₂Sn
• 分子量: 369.091
• InChiKey: BGQGOSISNLANIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-di-n-Butyl-4-phenyl-1,3,2-dioxastannole 在 三氯化锑 作用下， 以 苯 为溶剂， 反应 4.0h， 以85%的产率得到2-Chloro-4-phenyl-1,3,2-dioxastibole
  参考文献：
  名称：

  Anchisi, Carlo; Corda, Luciana; Maccioni, Antonio, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 141 - 144

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基乙二醇 、 二正丁基氧化锡 以 甲苯 为溶剂， 以>99的产率得到2,2-di-n-Butyl-4-phenyl-1,3,2-dioxastannole
  参考文献：
  名称：

  IVA 族有机金属试剂。2. 无手性助剂的 1,2-二醇对映体纯度的 NMR 光谱测定

  摘要：

  Le propanediol-1,2 et l'ethanediol-1,2(phenyl-«1») sont convertis en dioxastannolanes-1,3,2 dibutyl-2,2 au moyen de reactifs non chiraux

  DOI：

  10.1021/ja00276a027

文献信息

• Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight
  作者：Michael J. Martinelli、Rajappa Vaidyanathan、Joseph M. Pawlak、Naresh K. Nayyar、Ulhas P. Dhokte、Christopher W. Doecke、Lisa M. H. Zollars、Eric D. Moher、Vien Van Khau、Berta Košmrlj

  DOI：10.1021/ja016031r

  日期：2002.4.1

  This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of Sn-119 NMR studies.
• Organotin-Mediated Monoacylation of Diols with Reversed Chemoselectivity. Mechanism and Selectivity¹
  作者：Stefano Roelens

  DOI：10.1021/jo960453f

  日期：1996.1.1

  The monoesterification of unsymmetrically substituted diols, which occurs at the most substituted hydroxyl when activation of the substrate is achieved through its dibutylstannylene acetal, has been investigated to ascertain the origin of the unusual reversal of chemoselectivity. A mechanism in which the dibutylstannylene acetal plays the double role of reagent and catalyst has been established, which accounts for the reactivity, selectivity, and product distribution of the reaction, The reaction pathway involves three subsequent steps, namely, (a) esterification, (b) intra- and intermolecular transesterification, and (c) quench; interplay between kinetic and thermodynamic control over the three steps is responsible for the observed product distribution. The knowledge of the reaction mechanism allows for adjustment of experimental conditions to achieve optimum selectivity, which can be >99% with the appropriate choice of reagents. The stannylation procedure converts hydroxyls into functional groups highly chemoselective toward acyl reagents, but inert toward sulfonyl halides and alkylating reagents. The reactivity of the Sn-O bond has been found to decrease with decreasing the electronegativity of ligands on tin, while halide ligands appear to be essential for reversal of chemoselectivity. A structure has been proposed for the catalytic species, in which complexation of the stannyl monoester intermediates with the starting dioxastannolane reagent activates the stannylated oxygen toward addition to the carbonyl and at the same time accounts for the steric hindrance that biases the intramolecular transesterification equilibrium toward the thermodynamically most stable monoester of the most substituted hydroxyl.
• Diol-tin ketal as effective catalyst in the tin mediated benzoylation of polyols
  作者：Ezio Fasoli、Antonio Caligiuri、Stefano Servi、Davide Tessaro

  DOI：10.1016/j.molcata.2005.08.042

  日期：2006.2

  The monobenzoylation of 1-phenyl-1,2-ethanediol in the presence of different tin reagent has been studied. The stannylene ketal of 1-phenyl-1,2-ethanediol has been prepared and used as a catalyst or generated in situ by exchange with other mixed tin ketals. In either case, the acylation occurs rapidly with 2 mol% of the catalyst with the known selectivity. These experiments clearly establish the catalytic nature of the acylation reaction. (c) 2005 Elsevier B.V. All rights reserved.
• Yano, Katsunori; Baba, Akio; Matsuda, Haruo, Chemische Berichte, 1991, vol. 124, # 8, p. 1881 - 1884
  作者：Yano, Katsunori、Baba, Akio、Matsuda, Haruo

  DOI：——

  日期：——
• MORDINI, ALESSANDRO;ROELENS, STEFANO, J. ORG. CHEM., 54,(1989) N1, C. 2643-2645
  作者：MORDINI, ALESSANDRO、ROELENS, STEFANO

  DOI：——

  日期：——