(E)-tributyl(2-(thiophen-3-yl)vinyl)stannane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-tributyl(2-(thiophen-3-yl)vinyl)stannane
• 英文别名: (E)-1-(3-thiophenyl)-2-tributylstannylethene；tributyl-[(E)-2-thiophen-3-ylethenyl]stannane
• 化学式: C₁₈H₃₂SSn
• 分子量: 399.228
• InChiKey: WTGNVXXLAGSGOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-tributyl(2-(thiophen-3-yl)vinyl)stannane 在 bis-triphenylphosphine-palladium(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 1,2-双(二苯基膦)乙烷 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 2.0h， 生成 4-ethoxycarbonyl-6-(3-thienyl)-1-(p-toluenesulfonyl)-1,6-dihydropyridin-2(3H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric 6-Endo Cyclization of Dienamides with Substituent-Driven Activation

  摘要：

  Chiral 2-piperidinone compounds with various C-6 substituents were successfully synthesized via a Pd-catalyzed asymmetric 6-endo cyclization of dienamides, which were evidently activated by both N-p-toluenesulfonyl and C-3 ester substituents.

  DOI：

  10.1021/ol300737t
• 作为产物：
  描述：

  3-乙炔基噻吩 、 叔丁基锡烷 在 potassium fluoride 、 18-冠醚-6 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以44%的产率得到(E)-tributyl(2-(thiophen-3-yl)vinyl)stannane
  参考文献：
  名称：

  Illuminating Stannylation

  摘要：

  DOI：

  10.1021/jacs.1c00887

文献信息

• Stereocontrolled Synthesis of Substituted Chiral Piperidines viaOne-Pot Asymmetric 6π-Azaelectrocyclization: Asymmetric Syntheses of(−)-Dendroprimine, (+)-7-Epidendroprimine, (+)-5-Epidendroprimine, and (+)-5,7-Epidendroprimine
  作者：Toyoharu Kobayashi、Futoshi Hasegawa、Yoshikatsu Hirose、Katsunori Tanaka、Hajime Mori、Shigeo Katsumura

  DOI：10.1021/jo202350z

  日期：2012.2.17

  presence of a Pd(0) catalyst stereoselectively produced the tetracyclic aminoacetal compounds, resulting from the four-bond formation accompanying by controlling the stereochemistry at the two asymmetric centers. The produced cyclic aminoacetals can be regarded as synthetic precursors of substituted chiral piperidines, and the syntheses of 2,4- and 2,4,6-substituted piperidines were realized from the obtained

  烯基乙烯基锡，乙基（Z）-2-碘-4-氧代丁烯酸酯和（-）-7-异丙基-顺式的不对称一锅法6π-氮杂电环化-氨基茚满醇在Pd（0）催化剂存在下立体选择性地产生四环氨基缩醛化合物，这是由于通过控制两个不对称中心的立体化学而伴随的四键形成。可以将产生的环状氨基缩醛视为取代的手性哌啶的合成前体，并且通过与C键合的双键的立体选择性氢化，从获得的氨基缩醛中合成2,4-和2,4,6-取代的哌啶。 -4酯基和氨基缩醛部分的烷基化。此外，吲哚并立生物碱，（-）-dendroprimine及其三种立体异构体（+）-7-乙二苯丙氨酸，（+）-5-乙二苯丙氨酸和（+）-5,7-乙二苯丙氨酸是立体选择性合成的。实现。
• [1,5]-H Shift of Aldehyde Hydrogen in Dienal Compounds to Produce Ketenes
  作者：Taku Sakaguchi、Yudai Okuno、Yohei Tsutsumi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1021/ol2016302

  日期：2011.8.19

  In 3-ethoxycarbonyl-2,4-dienal compounds, a thermal [1,5]-H shift of aldehyde hydrogen easily proceeded to produce the corresponding vinyl ketenes due to the remarkable substituent effect caused by the C3 ester group. The produced ketenes were captured by an alcohol and olefins to afford the corresponding esters and four-membered ring compounds, respectively.

  在3-乙氧基羰基-2,4-二烯化合物中，由于C3酯基团引起的显着取代作用，醛氢的热[1,5] -H转移很容易进行以生成相应的乙烯基烯酮。生成的乙烯酮被醇和烯烃捕获，分别得到相应的酯和四元环化合物。
• Library-directed Solution- and Solid-phase Synthesis of 2,4-Disubstituted Pyridines: One-pot Approach through 6 π-Azaelectrocyclization
  作者：Taku Sakaguchi、Toyoharu Kobayashi、Sho Hatano、Hiroshi Tsuchikawa、Koichi Fukase、Katsunori Tanaka、Shigeo Katsumura

  DOI：10.1002/asia.200900146

  日期：2009.10.5

  for the synthesis of 2,4‐disubstituted pyridines has been successfully established. The method proceeds through a 6π‐azaelectrocyclization‐aromatization sequence. Using this method, a wide variety of pyridine structures substituted at the 2‐position have been rapidly constructed from vinyl stannanes, vinyl iodide, sulfonamide, and a palladium catalyst. The method was further applied to the solid‐phase

  已经成功地建立了一种有效的一锅合成方法，用于合成2,4-二取代的吡啶。该方法通过6π-氮杂电环化-芳香化序列进行。使用这种方法，已经迅速从乙烯基锡烷，乙烯基碘，磺酰胺和钯催化剂构建了在2位取代的吡啶结构。该方法进一步应用于固相合成，其中使用“无痕”磺酰胺连接剂可以快速制备少量的高纯度吡啶类化合物，而无需进行色谱分离。
• Efficient synthesis of 2,4,5-trisubstituted 2,5-chiral tetrahydropyridines using a one-pot asymmetric azaelectrocyclization protocol
  作者：Toyoharu Kobayashi、Kenichi Takeuchi、Junichi Miwa、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1039/b900897g

  日期：——

  The stereocontrolled synthetic procedure for the preparation of 2,4,5-trisubstituted 2,5-chiral 1,2,5,6-tetrahydropyridines was established using a one-pot asymmetric azaelectrocyclization protocol; the generality of this protocol was demonstrated by synthesizing the title compounds with various aryl and alkenyl substituents at the C-2 position.

  使用一锅式不对称氮杂电环化方案建立了制备2,4,5-三取代的2,5-手性1,2,5,6-四氢吡啶的立体控制合成程序；通过合成在C-2位置带有各种芳基和烯基取代基的标题化合物，证明了该方案的普遍性。
• New type of azacyclization: thermal preparation of 4,6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect
  作者：Yuya Maekawa、Taku Sakaguchi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1016/j.tetlet.2011.12.014

  日期：2012.2

  The thermal 6-endo cyclization of N-sulfonyl-2,4-dienamide compounds to produce 4,6-disubstituted 2-piperidinone is described. The observed remarkable substituent effect due to the N-sulfonyl and C3 ethoxycarbonyl groups for acceleration of this 6-endo cyclization strongly suggests that the reaction would proceed via the 6 pi-azaelectrocyclization of the intermediary imidic acid. On the contrary, the corresponding 5-formyl and 5-acetyl derivatives rapidly cyclized at room temperature to produce the 5-exo cyclized products. (C) 2011 Elsevier Ltd. All rights reserved.