(E)-N,N-dimethyl-2-(4-(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)phenoxy)ethanamine | 1421712-14-2

• 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)-N,N-dimethyl-2-(4-(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)phenoxy)ethanamine
• 英文别名: N,N-dimethyl-2-[4-[(E)-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-enyl]phenoxy]ethanamine
• CAS: 1421712-14-2
• 化学式: C₂₆H₃₆BNO₃
• 分子量: 421.388
• InChiKey: XAVOHPZBBUGZQO-VHXPQNKSSA-N

物化性质

• 沸点：
  491.0±55.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碘苯 、 (E)-N,N-dimethyl-2-(4-(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)phenoxy)ethanamine 在 三叔丁基膦 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以93%的产率得到他莫昔芬
  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：

  联硼酸频那醇酯 在 copper(l) iodide 、 copper diacetate 、 三苯基膦 、 lithium chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 (E)-N,N-dimethyl-2-(4-(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)phenoxy)ethanamine
  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 Cross-Coupling of Boronic Esters with Aryl Iodides and Application to the Carboboration of Alkynes and Allenes
  作者：Yiqing Zhou、Wei You、Kevin B. Smith、M. Kevin Brown

  DOI：10.1002/anie.201310275

  日期：2014.3.24

  Copper‐catalyzed Suzuki–Miyaura‐type cross‐coupling and carboboration processes are reported. The cross‐couplings function well with a variety of substituted aryl iodides and aryl boronic esters and allows for orthogonal reactivity compared to palladium‐catalyzed processes. The carboboration method includes both alkynes and allenes and provides access to highly substituted and stereodefined vinyl boronic

  据报道，铜催化的铃木-宫浦型交叉偶联和碳硼化过程。与各种取代的芳基碘化物和芳基硼​​酸酯的交叉偶联作用很好，并且与钯催化的方法相比，具有正交的反应性。碳硼化方法包括炔烃和丙二烯，并提供了高度取代的和立体定义的乙烯基硼酸酯的途径。简单的一锅合成他莫昔芬强调了炔烃的碳硼化方法。
• 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.