(E)-tributyl(1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)stannane | 1421712-13-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-tributyl(1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)stannane
• CAS: 1421712-13-1
• 化学式: C₃₂H₄₉BO₂Sn
• 分子量: 595.261
• InChiKey: KFMZQMZWBLQEIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三正丁基甲氧基锡 、 二苯基乙炔 、 联硼酸频那醇酯 在 copper diacetate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以87%的产率得到(E)-tributyl(1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)stannane
  参考文献：
  名称：

  Copper-Catalyzed Three-Component Borylstannylation of Alkynes

  摘要：

  AbstractRegio‐ and stereoselective installation of boryl and stannyl moieties into a carbon–carbon triple bond of various alkynes has been achieved based on a three‐component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate–tricyclohexylphosphine complex, giving diverse vic‐borylstannylalkenes in a straightforward manner. Carbon–tin and carbon–boron bonds of the resulting borylstannylation product are successively transformed into carbon–carbon bonds by a Migita–Kosugi–Stille and a Suzuki–Miyaura coupling, leading to the formation of (Z)‐tamoxifen with anti‐breast cancer activity.

  DOI：

  10.1002/chem.201202435

文献信息

• Copper-Catalyzed Borylstannylation of Alkynes with Tin Fluorides
  作者：Hiroto Yoshida、Miki Kimura、Itaru Osaka、Ken Takaki

  DOI：10.1021/acs.organomet.7b00058

  日期：2017.4.10

  Tin fluorides were found to be suitable electrophiles for the copper-catalyzed borylstannylation of terminal alkynes with bis(pinacolato)diboron to afford cis-vic-boryl(stannyl)alkenes straightforwardly. A fluorine atom proved to play a pivotal role in generating a key catalytic intermediate, a borylcopper species, both in the induction period and in the sigma-bond metathesis step.
• Copper-Catalyzed Three-Component Borylstannylation of Alkynes
  作者：Yuki Takemoto、Hiroto Yoshida、Ken Takaki

  DOI：10.1002/chem.201202435

  日期：2012.11.12

  AbstractRegio‐ and stereoselective installation of boryl and stannyl moieties into a carbon–carbon triple bond of various alkynes has been achieved based on a three‐component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate–tricyclohexylphosphine complex, giving diverse vic‐borylstannylalkenes in a straightforward manner. Carbon–tin and carbon–boron bonds of the resulting borylstannylation product are successively transformed into carbon–carbon bonds by a Migita–Kosugi–Stille and a Suzuki–Miyaura coupling, leading to the formation of (Z)‐tamoxifen with anti‐breast cancer activity.