(phenylthiomethyl)tributylstannane | 34694-32-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (phenylthiomethyl)tributylstannane
• CAS: 34694-32-1
• 化学式: C₁₉H₃₄SSn
• 分子量: 413.255
• InChiKey: YYWSMUMPMNVDNH-UHFFFAOYSA-N

物化性质

• 沸点：
  413.4±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴丁基-镁 、 (phenylthiomethyl)tributylstannane 以 四氢呋喃 、 乙醚 为溶剂， 生成 四丁基锡
  参考文献：
  名称：

  Tin–magnesium transmetallation reactions

  摘要：

  Sulfur-functionalized methyltin compounds nBu(3)SnCH(2)S(O)(i)R (i = 0, 1, 2; R = Me, Ph) underwent transmetallation with Grignard compounds MgR'X (R' = Me, nBu, Ph; X = Cl, Br, I) and diorganomagnesium compounds MgR'R" (R'/R" = Me/Me, nBu-sBu) to provide Sn(nBu)(3)R and Mg[CH2S(O)(i)R]X and Mg[CH2S(O)(i)R]R", respectively. Analogously, the reaction of nBu(3)SnCH(2)P(O)Ph-2 with Mg(nBu)Br afforded quantitatively Mg[CH2P(O)Ph-2]Br and Sn(nBu)(4). Transmetallations between it Bu3SnCH2YMe2 (Y = N, P) and MgMe2 proceeded only in the presence of catalytic amounts (10-20 mol%) of Lin Bu yielding Mg(CH2YMe2)Me and Sn(nBu)(3)Me/Sn(nBu)(4). (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01430-4
• 作为产物：
  描述：

  ethyl 2-(tributylstannyl)acetate 以 苯 为溶剂， 生成 (phenylthiomethyl)tributylstannane
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.5.2, page 276 - 305

  摘要：

  DOI：

文献信息

• Generation of<i>α</i>-Alkylthio Radicals by Photoinduced One-Electron Oxidation of<i>α</i>-Stannyl Sulfides and Their Use for Carbon-Carbon Bond Formation
  作者：Taketo Ikeno、Manabu Harada、Noriyoshi Arai、Koichi Narasaka

  DOI：10.1246/cl.1997.169

  日期：1997.2

  Cation radicals, generated from α-stannyl sulfides by the photoinduced single electron transfer, cleave into α-alkylthio radical intermediates with the elimination of the stannyl group. The α-alkylthio radicals thus formed are utilized for carbon-carbon bond forming reactions.

  通过光诱导的单电子转移，从α-锡基硫化物生成的阳离子自由基会裂解成α-烷硫基自由基中间体，同时消除锡基团。形成的α-烷硫基自由基可用于碳-碳键形成反应。
• gem-Heterosubstituted (stannyl)methylsilanes as synthetic equivalents of functionalized α-stannyl(methyl) anions
  作者：Damiano Tanini、Tiziano Nocentini、Antonella Capperucci

  DOI：10.24820/ark.5550190.p011.038

  日期：——

  Received mm-dd-yyyy Accepted mm-dd-yyyy Published on line mm-dd-yyyy Dates to be inserted by editorial office Abstract α-Heterosubstituted silyl derivatives, such as phenylthio-, phenylselenoand benzotriazolyl-stannyl silanes, react with aldehydes under TBAF catalysis, leading to α-substituted-β-hydroxy stannanes, able to behave as precursors of Zand E-olefins, generated by deoxystannylation. This

  收到 mm-dd-yyyy 接受 mm-dd-yyyy 在线发布 mm-dd-yyyy 编辑部插入的日期 摘要 α-杂取代的甲硅烷基衍生物，如苯硫基、苯基硒基和苯并三唑基-甲锡基硅烷，在 TBAF 下与醛反应催化，导致 α-取代-β-羟基锡烷，能够充当 Zand E-烯烃的前体，由脱氧锡烷基化产生。这种反应性表明这种杂取代的硅烷能够通过碳-硅键的温和官能化充当掩蔽的碳负离子。
• Electrooxidative coupling of α-heteroatom-substituted organostannanes and organosilanes
  作者：Jun-ichi Yoshida、Masanori Itoh、Sachihiko Isoe

  DOI：10.1039/c39930000547

  日期：——

  Anodic oxidation of α-heteroatom-substituted organostannanes in the presence of organosilanes such as allylsilanes and silyl enol ethers results in the facile cleavage of the carbon–tin bond and introduction of allyl and acyl groups onto the carbon, respectively.

  在存在如烯丙基硅烷和硅醇醚等有机硅化合物的情况下，对α-杂原子取代的有机锡化合物进行阳极氧化，会促进碳-锡键的轻松断裂，并分别将烯丙基和酰基引入碳上。
• Homologation of halostannanes with carbenoids: a convenient and straightforward one-step access to α-functionalized organotin reagents
  作者：Saad Touqeer、Laura Castoldi、Thierry Langer、Wolfgang Holzer、Vittorio Pace

  DOI：10.1039/c8cc04786c

  日期：——

  A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented. Critical for the success of the operation is the excellent nucleophilicity of carbenoid-like methyllithium reagents (LiCHXY, X, Y = halogen, OR, and CN): by simply individuating the reagents’ substitution pattern, the desired functionalized fragment is delivered to the

  文献记载了卤代烷烃直接，单一的合成同源性转化为单取代或二取代的甲基类似物。操作成功的关键是类胡萝卜素样甲基锂试剂（LiCHXY，X，Y =卤素，OR和CN）的优异亲核性：通过简单地区分试剂的取代方式，所需的官能化片段将被递送至亲电子试剂。在类似的卤代compounds化合物的情况下，也证明了该方案的广泛范围。还讨论了亲核试剂的串联同源猝灭和α-氯烯丙基锂的使用。
• Silyl-Substituted Dithioles as Candidates for New Electron Donors
  作者：Hongqi Li、Keiji Nishiwaki、Kenichiro Itami、Jun-ichi Yoshida

  DOI：10.1246/bcsj.74.1717

  日期：2001.9

  3-benzodithioles as candidates for new electron donors. The oxidation potential of monosilyl-substituted 1,3-benzodithiole was found to be significantly less positive than that of the parent 1,3-benzodithiole. The introduction of the second silyl group caused further decrease of the oxidation potential. Compounds composed of two 1,3-benzodithiole units linked by a silyl group were also synthesized. These

  分子轨道计算表明，在 1,3-二硫醇的 2-位引入甲硅烷基会导致电离电位显着降低，并且 2-甲硅烷基-1,3-二硫醇充当伪 π 电子系统。甲硅烷基还可用作连接 π 电子系统以实现人工堆叠的桥梁。这些概念引导我们设计和合成甲硅烷基取代的 1,3-苯二硫醇作为新电子供体的候选物。发现单甲硅烷基取代的 1,3-苯二硫醇的氧化电位明显低于母体 1,3-苯二硫醇的氧化电位。第二个甲硅烷基的引入导致氧化电位进一步降低。还合成了由两个由甲硅烷基连接的 1,3-苯并二硫醇单元组成的化合物。这些显示出与相应单体化合物相当的氧化电位。发现甲硅烷基取代对 1,3-二硫醇的 2-位的影响大于...