(Z)-4-phenyl-1-(tributylstannyl)butene | 138034-96-5

• 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: (Z)-4-phenyl-1-(tributylstannyl)butene
• 英文别名: tributyl(4-phenylbut-1-en-1-yl)stannane
• CAS: 138034-96-5
• 化学式: C₂₂H₃₈Sn
• 分子量: 421.254
• InChiKey: SJYXDHJKERLKLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  1-iodo-3-(tetrahydropyran-2-yloxy)propane 、 (Z)-4-phenyl-1-(tributylstannyl)butene 在 bis(η3-allyl-μ-chloropalladium(II)) PCy(1-pyrrolidinyl)2 、 3 A molecular sieve 、 四甲基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2-[(Z)-7-phenylhept-4-enoxy]oxane
  参考文献：
  名称：

  钯催化烷基卤化物交叉偶联的配体：烷基二氨基膦的使用扩大了Stille反应的范围。

  摘要：

  DOI：

  10.1002/anie.200352668
• 作为产物：
  描述：

  1-(溴乙炔基)-4-氟苯 、 三正丁基氢锡 在 tris(dibenzylideneacetone)dipalladium (0) 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(Z)-4-phenyl-1-(tributylstannyl)butene
  参考文献：
  名称：

  Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes

  摘要：

  重点介绍了一种包含多种氧和氮官能团的(E)-1-锡烷基-1-烯的实用合成方法，涉及1-溴炔的氢锡化反应，随后通过钯催化的碳-溴键断裂反应。

  DOI：

  10.1039/p19960002417

文献信息

• Room-Temperature Stille Cross-Couplings of Alkenyltin Reagents and Functionalized Alkyl Bromides that Possess β Hydrogens
  作者：Karsten Menzel、Gregory C. Fu

  DOI：10.1021/ja0344563

  日期：2003.4.1

  communication describes a significant expansion in the scope of Stille reactions of Csp3-X electrophiles, specifically, that Pd/P(t-Bu)2Me catalyzes the room-temperature cross-coupling of a variety of functionalized, beta-hydrogen-containing alkyl bromides with an array of alkenyltin reagents. The structure of the phosphine (P(t-Bu)2Me) is well suited for facilitating oxidative addition and avoiding beta-hydride

  这篇通讯描述了 Csp3-X 亲电试剂的 Stille 反应范围的显着扩展，特别是 Pd/P(t-Bu)2Me 催化了各种功能化的、含​​ β-氢的烷基的室温交叉偶联溴化物与一系列烯基锡试剂。膦 (P(t-Bu)2Me) 的结构非常适合促进氧化加成和避免β-氢化物消除，而氟化物用于激活锡试剂以实现有效的金属转移。
• Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (<i>Z</i>)-Alkenyl Compounds
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu、Jiro Tsuji

  DOI：10.1021/jo9812781

  日期：1998.11.1

  The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl-conjugated 1,l-dibromo-l-alkenes 7a-h and 2,2-disubstituted I,1-dibromo-1-alkenes 9a-f. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,l-dibromo-l-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.
• Illuminating Stannylation
  作者：Kyoka Sakamoto、Yuki Nagashima、Chao Wang、Kazunori Miyamoto、Ken Tanaka、Masanobu Uchiyama

  DOI：10.1021/jacs.1c00887

  日期：2021.4.21