(E)-tributyl(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)stannane | 1421712-24-4

• 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: (E)-tributyl(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)stannane
• CAS: 1421712-24-4
• 化学式: C₂₈H₄₉BO₂Sn
• 分子量: 547.217
• InChiKey: LLVVHCQSMXIZSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-tributyl(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)stannane 在 copper(l) iodide 、 三叔丁基膦 、 三苯基膦 、 lithium chloride 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 他莫昔芬
  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
• 作为产物：
  描述：

  1-苯基-1-丁炔 、 三正丁基甲氧基锡 、 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 15.0h， 以82%的产率得到(E)-tributyl(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)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 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.