N-[chloro(hept-4-yn-2-yloxy)boranyl]-N-propan-2-ylpropan-2-amine | 871114-36-2

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: N-[chloro(hept-4-yn-2-yloxy)boranyl]-N-propan-2-ylpropan-2-amine
• CAS: 871114-36-2
• 化学式: C₁₃H₂₅BClNO
• 分子量: 257.612
• InChiKey: WUFZIPIYDCVRMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  N-[chloro(hept-4-yn-2-yloxy)boranyl]-N-propan-2-ylpropan-2-amine 在 bis(1,5-cyclooctadiene)nickel (0) 、 sodium hydroxide 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 48.0h， 生成 (1E,3E)-4-ethyl-1,6-diphenyl-3-(2-hydroxypropyl)hex-1,3-dien-5-yne
  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：

  4-庚炔-2-醇 、 二氯(二异丙基氨基)硼烷 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以87%的产率得到N-[chloro(hept-4-yn-2-yloxy)boranyl]-N-propan-2-ylpropan-2-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