N-[chloro(1,4-diphenylbut-3-ynoxy)boranyl]-N-propan-2-ylpropan-2-amine | 871114-38-4

• 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: N-[chloro(1,4-diphenylbut-3-ynoxy)boranyl]-N-propan-2-ylpropan-2-amine
• CAS: 871114-38-4
• 化学式: C₂₂H₂₇BClNO
• 分子量: 367.726
• InChiKey: YUUMYWSWEADRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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(1,4-diphenylbut-3-ynoxy)boranyl]-N-propan-2-ylpropan-2-amine 在 吡啶 、 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.0h， 生成 (Z)-1-acetoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,4,6-triphenylhex-3-en-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：

  二氯(二异丙基氨基)硼烷 、 1,4-diphenylbut-3-yn-1-ol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 N-[chloro(1,4-diphenylbut-3-ynoxy)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