1-butenyltributylstannane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: 1-butenyltributylstannane
• 英文别名: (E)-but-2-enyltributylstannane；but-1-enyl-tri-n-butylstannane
• 化学式: C₁₆H₃₄Sn
• 分子量: 345.156
• InChiKey: IEAMEXAZVVYIPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  2-bromo-3-methoxy-2-cyclohexenone 、 1-butenyltributylstannane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到2-[(E)-but-1-enyl]-3-methoxycyclohex-2-en-1-one
  参考文献：
  名称：

  An efficient synthesis of 2-aryl and 2-alkenyl-3-alkoxy-cyclohexenones by a modified Stille reaction

  摘要：

  A general, direct procedure for the synthesis of 2-aryl and 2-alkenyl-3-alkoxy-cyclohexenones using a modified Stille coupling is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02424-1
• 作为产物：
  描述：

  (4-Methylphenoxy)-(1-tributylstannylbutoxy)methanethione 以55%的产率得到
  参考文献：
  名称：

  DUBOUDIN, J. GEORGES;RATIER, MAX;TROUVE, BRUNO, J. ORGANOMET. CHEM., 331,(1987) N 2, 181-191

  摘要：

  DOI：

文献信息

• Total Synthesis of (+)-Gregatin B and E
  作者：Taichi Kusakabe、Yasuko Kawai、Keisuke Kato

  DOI：10.1021/ol402472q

  日期：2013.10.4

  The first total synthesis of (+)-gregatin E and a new total synthesis of (+)-gregatin B are described. Key features of our synthetic approach involve a palladium-catalyzed cyclization–methoxycarbonylation of optically active propargylic acetate and a Suzuki–Miyaura coupling or CuTC-mediated coupling reaction. The absolute configuration of (+)-gregatin E (5R,5′S) is proposed.

  描述了（+）-凝集素E的第一个全合成和（+）-凝集素B的新的全合成。我们的合成方法的关键特征包括光学活性的乙酸炔丙酯的钯催化环化-甲氧基羰基化和Suzuki-Miyaura偶联或CuTC介导的偶联反应。提出了（+）-聚集蛋白E（5 R，5 'S）的绝对构型。
• Asymmetric Hydrovinylation of Vinylindoles. A Facile Route to Cyclopenta[<i>g</i>]indole Natural Products (+)-<i>cis</i>-Trikentrin A and (+)-<i>cis</i>-Trikentrin B
  作者：Wang Liu、Hwan Jung Lim、T. V. RajanBabu

  DOI：10.1021/ja3004733

  日期：2012.3.28

  Vinylindoles undergo Ni(II)-catalyzed asymmetric hydrovinylation under very mild conditions (-78 °C, 1 atm ethylene, 4 mol % catalyst) to give the corresponding 2-but-3-enyl derivatives in excellent yields and enantioselectivities. Hydroboration of the alkene and oxidation to an acid, followed by Friedel-Crafts annulation, gives an indole-annulated cyclopentanone that is a suitable precursor for the

  乙烯基吲哚在非常温和的条件下（-78 °C，1 atm 乙烯，4 mol% 催化剂）进行 Ni(II) 催化的不对称加氢乙烯基化，以优异的产率和对映选择性得到相应的 2-but-3-enyl 衍生物。烯烃的硼氢化和氧化成酸，然后进行 Friedel-Crafts 环化，得到吲哚环化的环戊酮，它是合成顺式三链酮和所有已知的草药的合适前体。例如，来自 4-乙基-7-乙烯基吲哚的环戊酮通过四步（Wittig 反应、烯烃异构化、非对映选择性氢化和氮脱保护）转化为 (+)-cis-trikentin A。先前从 (S)-(-)-苹果酸合成该分子涉及 20 多个步骤和非对映异构中间体的制备型 HPLC 分离。
• First total synthesis of haplacutine C
  作者：Noriki Kutsumura、Keisuke Numata、Takao Saito

  DOI：10.1016/j.tetlet.2016.10.070

  日期：2016.12

  A total synthesis of haplacutine C has been achieved. The synthetic key features were the intramolecular aldol condensation for construction of the 4-quinolinone skeleton and the Stille coupling for elongation of the dienol side chain. In addition, the 4-O-protected-quinolines were also utilized as the synthetic equivalents of 4-quinolinone at the stage of side chain transformation.

  已经完成了pla庚啶C的全合成。合成的关键特征是用于构建4-喹啉酮骨架的分子内羟醛缩合和用于延长二烯醇侧链的Stille偶联。另外，在侧链转化阶段，还将4- O-保护的喹啉用作4-喹啉酮的合成等同物。
• Synthèse et thermolyse éclair d'esters α-tributylstanniques
  作者：J. Georges Duboudin、Max Ratier、Bruno Trouve

  DOI：10.1016/0022-328x(87)80020-7

  日期：1987.9
• Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling
  作者：Nalin Chandrasoma、Neil Brown、Allen Brassfield、Alok Nerurkar、Susana Suarez、Keith R. Buszek

  DOI：10.1016/j.tetlet.2012.11.125

  日期：2013.2

  An efficient total synthesis of the annulated indole natural product(+/-)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis. (C) 2012 Elsevier Ltd. All rights reserved.