(triethylgermyl)tributylstannane | 181476-24-4

• 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: (triethylgermyl)tributylstannane
• 英文别名: tributyl(triethylgermyl)stannane
• CAS: 181476-24-4
• 化学式: C₁₈H₄₂GeSn
• 分子量: 449.831
• InChiKey: XGKUQOUKSYCUEV-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (triethylgermyl)tributylstannane 、 3-氯苯乙炔 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三羟甲基丙烷亚磷酸酯 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(Z)-1-(tributylstannyl)-1-(m-chlorophenyl)-2-(triethylgermyl)ethene
  参考文献：
  名称：

  Synthesis of (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes and the related ethenes, precursors to stereodefined germylethenes, via Pd(dba)2–P(OCH2)3CEt-catalyzed germastannation of acetylenes in THF

  摘要：

  (Z)-1-Aryl-2-(germyl)-1-(stannyl)ethenes are synthesized in high yields by the addition of tributyl(triethylgermyl)stannane to arylacetylenes catalyzed by a specific combination catalyst, Pd(dba)(2) and 4-ethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, in tetrahydrofuran. Ethynylthiophene and 2-methyl-3-butyn-2-ol are also subject to the germastannation to afford the respective adducts in high yields. In addition, the J(Sn-H) and C-13-NMR data for their adducts are presented. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00652-0

文献信息

• Methods for Forming Protected Organoboronic Acids
  申请人：Burke Martin D.

  公开号：US20110201806A1

  公开（公告）日：2011-08-18

  Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.

  描述了形成受保护硼酸的方法，以一种简单、可扩展和具有成本效益的方式提供各种建筑模块，例如包含复杂和/或药用重要结构的建筑模块，并/或提供简单或复杂的受保护有机硼酸建筑模块。第一种方法包括将亚胺二羧酸与有机硼酸盐反应。第二种方法包括将N-取代吗啉二酮与有机硼酸反应。
• Palladium complex-catalyzed germylation of allylic halides using (germyl)stannanes
  作者：Taichi Nakano、Kazuyoshi Ono、Yoshiya Senda、Toshihiko Migita

  DOI：10.1016/s0022-328x(00)00620-3

  日期：2001.1

  (Triethylgermyl)tributylstannane reacts metal-selectively with allylic halides at room temperature (r.t.) in the presence of tris(dibenzylideneacetone)dipalladium, Pd2(dba)3CHCl3, to provide an alternative route to allylgermanes. (Dimethylphenylgermyl)tributylstannane regio- and stereoselectively reacts more readily with allylic halides than (triethylgermyl)tributylstannane affording the corresponding allylgermanes

  （三乙基锗基）三丁基锡烷在室温（rt）下在三（二亚苄基丙酮）二钯，Pd 2（dba）3 CHCl 3的存在下与金属烯丙基卤化物发生金属选择性反应，从而提供了另一种制备烯丙基锗烷的途径。与（三乙基锗基）三丁基锡烷相比，（二甲基苯基锗基）三丁基锡烷与烯丙基卤化物的区域和立体选择性反应更容易，以定量收率得到相应的烯丙基锗烷。
• A Simple and General Platform for Generating Stereochemically Complex Polyene Frameworks by Iterative Cross-Coupling
  作者：Suk Joong Lee、Thomas M. Anderson、Martin D. Burke

  DOI：10.1002/anie.201004911

  日期：2010.11.15

  Not so complex: A novel iterative cross‐coupling strategy provides access to useful building blocks that enable the simple preparation of complex polyene natural‐product motifs in all possible stereoisomeric forms. The method was used to synthesize the polyene core of vacidin A (see structure).

  不那么复杂：一种新颖的迭代交叉偶联策略提供了有用的构建模块，能够以所有可能的立体异构形式简单地制备复杂的多烯天然产物基序。该方法用于合成 vacidin A 的多烯核（见结构）。
• Alternative Synthesis of (<i>Z</i>)-1-Aryl-1-(tributylstannyl)-2-(triethylgermyl)ethenes and the Unprecedented Germyl 1,2-Migration during the Destannylation of the Adducts
  作者：Taichi Nakano、Yoshiya Senda、Takashi Miyamoto

  DOI：10.1246/cl.2000.1408

  日期：2000.12

  A specific combination catalyst, Pd(dba)2 and 4-ethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, effectively catalyzed the addition of tributyl(triethylgermyl)stannane to arylacetylenes in tetrahydrofuran to give (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes in high yields. The (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes were subject to the unprecedented germyl 1,2-migration during the destannylation using HI / TBAI in toluene to produce 1-aryl-1-(germyl)ethenes in high yields.

  Pd(dba)2 和 4-乙基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷是一种特定的组合催化剂，可有效催化三丁基（三乙基锗基）锡与芳基乙炔在四氢呋喃中的加成反应，从而高产率地得到 (Z)-1- 芳基-2-（胚芽基）-1-（锡基）乙烯。在甲苯中使用 HI / TBAI 进行去烷基化时，(Z)-1-芳基-2-(胚芽基)-1-(锡基)乙烯会发生前所未有的胚芽基 1,2 迁移，从而以高产率生成 1-芳基-1-(胚芽基)乙烯。
• Synthesis of (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes and the related ethenes, precursors to stereodefined germylethenes, via Pd(dba)2–P(OCH2)3CEt-catalyzed germastannation of acetylenes in THF
  作者：Yoshiya Senda、Yoh-ichi Oguchi、Michihiro Terayama、Taijyu Asai、Taichi Nakano、Toshihiko Migita

  DOI：10.1016/s0022-328x(01)00652-0

  日期：2001.3

  (Z)-1-Aryl-2-(germyl)-1-(stannyl)ethenes are synthesized in high yields by the addition of tributyl(triethylgermyl)stannane to arylacetylenes catalyzed by a specific combination catalyst, Pd(dba)(2) and 4-ethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, in tetrahydrofuran. Ethynylthiophene and 2-methyl-3-butyn-2-ol are also subject to the germastannation to afford the respective adducts in high yields. In addition, the J(Sn-H) and C-13-NMR data for their adducts are presented. (C) 2001 Elsevier Science B.V. All rights reserved.