1-tri-n-butylstannyl-1-phenylthio-butane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-tri-n-butylstannyl-1-phenylthio-butane
• 化学式: C₂₂H₄₀SSn
• 分子量: 455.336
• InChiKey: NANJECBCHAWFPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2-环己烯-1-酮 、 1-tri-n-butylstannyl-1-phenylthio-butane 在 三甲基氯硅烷 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到3-((1-Phenylthio)butyl)-cyclohexanone
  参考文献：
  名称：

  Conjugate Addition of α-Sulfur-substituted Alkylstannanes to α,β-Unsaturated Ketones Mediated by a Copper(II) Triflate and Chlorotrimethylsilane Combination

  摘要：

  铜(II)三氟甲磺酸盐和氯三甲基硅烷的组合被发现对α-硫取代的烷基锡与α,β-不饱和酮的共轭加成有效。因此，相应的γ-硫取代酮以良好的产率获得。

  DOI：

  10.1246/cl.130284

文献信息

• Configurational stability of chiral organolithium compounds on the time scale of their addition to aldehydes
  作者：Reinhard W. Hofmann、Manfred Julius、Fabrice Chemla、Thomas Ruhland、Gerlinde Frenzen

  DOI：10.1016/s0040-4020(01)90457-0

  日期：1994.1

  A test based on kinetic resolution has been applied to the α-bromo-, α-phenylseleno- and α-phenylthio-alkyl-lithium compounds 1, which shows that addition of these species to the chiral aldehyde 6 occurs faster than enantiomer equilibration of the organolithium compounds.

  已对α-溴-，α-苯基硒代-和α-苯硫基-烷基-锂化合物1进行了基于动力学拆分的测试，结果表明，将这些物质添加到手性醛6中比对映体的对映体平衡要快。有机锂化合物。
• Copper(II) Triflate-mediated Addition Reaction of α-Sulfurated Alkylstannanes to Imines: Facile Synthesis of Vicinal-amino Sulfides
  作者：Hirotaka Kagoshima、Naoshi Takahashi

  DOI：10.1246/cl.2004.962

  日期：2004.8

  In the presence of copper(II) triflate, the addition reaction of α-sulfurated alkylstannanes to imines proceeded smoothly to give the corresponding vicinal-amino sulfides in good yields.

  在三氟甲磺酸铜 (II) 存在下，α-硫化烷基锡烷与亚胺的加成反应顺利进行，以良好的收率得到相应的邻氨基硫化物。
• A Convenient, Catalyst-free Cross-coupling Reaction of α-Sulfur-substituted Alkylstannanes with Acid Chlorides Leading to α-Sulfur-substituted Ketones
  作者：Hirotaka Kagoshima、Naoshi Takahashi

  DOI：10.1246/cl.2007.14

  日期：2007.1

  A thermal cross-coupling reaction of α-sulfur-substituted alkylstannanes with acid chlorides is described. A range of substrates can be used for the present reaction and the reaction proceeds by just mixing two components under reflux in mesitylene to give the corresponding α-sulfur-substituted ketones in good yields.

  描述了 α-硫代烷基锡烷与酸性氯化物的热交叉偶联反应。本反应可使用一系列底物，只需在甲苯甲醚回流条件下将两个组分混合，就能以良好的收率得到相应的α-硫代酮。
• Copper-catalyzed cross-coupling reaction of α-sulfur-substituted alkylstannanes with acid chlorides
  作者：Hirotaka Kagoshima、Naoshi Takahashi

  DOI：10.1016/j.tetlet.2013.06.088

  日期：2013.8

  Copper compounds were found to catalyze the cross-coupling reaction of a-sulfur-substituted alkylstannanes with acid chlorides. Under the optimized conditions (CuF2 (1 mol %), 1,4-dioxane, 102 degrees C), various substrates coupled to afford the corresponding a-sulfur-substituted ketones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Conjugate Addition of α-Sulfur-substituted Alkylstannanes to α,β-Unsaturated Ketones Mediated by a Copper(II) Triflate and Chlorotrimethylsilane Combination
  作者：Hirotaka Kagoshima、Takeshi Yahagi

  DOI：10.1246/cl.130284

  日期：2013.8.5

  The copper(II) triflate and chlorotrimethylsilane combination was found to be effective for the conjugate addition of α-sulfur-substituted alkylstannanes to α,β-unsaturated ketones. Thus, the corresponding γ-sulfur-substituted ketones were obtained in good yields.

  铜(II)三氟甲磺酸盐和氯三甲基硅烷的组合被发现对α-硫取代的烷基锡与α,β-不饱和酮的共轭加成有效。因此，相应的γ-硫取代酮以良好的产率获得。