Diisopropyl-{3-[3-methyl-1-phenylethynyl-but-2-en-(Z)-ylidene]-[1,2]oxaborolan-2-yl}-amine | 871114-44-2

• 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: Diisopropyl-{3-[3-methyl-1-phenylethynyl-but-2-en-(Z)-ylidene]-[1,2]oxaborolan-2-yl}-amine
• 英文别名: (3Z)-3-(5-methyl-1-phenylhex-4-en-1-yn-3-ylidene)-N,N-di(propan-2-yl)oxaborolan-2-amine
• CAS: 871114-44-2
• 化学式: C₂₂H₃₀BNO
• 分子量: 335.297
• InChiKey: ZNOIHPVOTNLQSF-DQRAZIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Diisopropyl-{3-[3-methyl-1-phenylethynyl-but-2-en-(Z)-ylidene]-[1,2]oxaborolan-2-yl}-amine 、 频哪醇 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (Z)-1-acetoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-4-(2-phenyl-1-ethyn-1-yl)-6-methylhept-3,5-diene
  参考文献：
  名称：

  Nickel-Catalyzed trans-Alkynylboration of Alkynes via Activation of a Boron−Chlorine Bond

  摘要：

  Reaction of (diisopropylamino)chloroboryl ethers of alkynols with alkynylstannanes in the presence of nickel catalysts afforded formal trans-alkynylboration products in good yields. The products were isolated as pinacol boronates after treatment of the crude reaction mixture with acetic anhydride and pinacol in the presence of a base. The trans-alkynylboration products underwent Suzuki-Miyaura coupling reaction with organic halides. A 2-borylalkenylnickel(II) complex, in which the boryl and nickel groups are located in a trans fashion, was isolated in a reaction of the chloroboryl ether with a single equivalent of a nickel(0)-phosphine complex.

  DOI：

  10.1021/ja055396z
• 作为产物：
  描述：

  bis(diisopropylamino)chloroborane 在 bis(1,5-cyclooctadiene)nickel (0) 、 三氯化硼-甲硫醚 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 Diisopropyl-{3-[3-methyl-1-phenylethynyl-but-2-en-(Z)-ylidene]-[1,2]oxaborolan-2-yl}-amine
  参考文献：
  名称：

  Nickel-Catalyzed trans-Alkynylboration of Alkynes via Activation of a Boron−Chlorine Bond

  摘要：

  Reaction of (diisopropylamino)chloroboryl ethers of alkynols with alkynylstannanes in the presence of nickel catalysts afforded formal trans-alkynylboration products in good yields. The products were isolated as pinacol boronates after treatment of the crude reaction mixture with acetic anhydride and pinacol in the presence of a base. The trans-alkynylboration products underwent Suzuki-Miyaura coupling reaction with organic halides. A 2-borylalkenylnickel(II) complex, in which the boryl and nickel groups are located in a trans fashion, was isolated in a reaction of the chloroboryl ether with a single equivalent of a nickel(0)-phosphine complex.

  DOI：

  10.1021/ja055396z