2-chloro-3-diphenylphosphanylquinoxaline | 1422239-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-chloro-3-diphenylphosphanylquinoxaline
• CAS: 1422239-77-7
• 化学式: C₂₀H₁₄ClN₂P
• 分子量: 348.771
• InChiKey: QKHUPXMGKPOKKK-UHFFFAOYSA-N

物化性质

• 沸点：
  467.3±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-chloro-3-diphenylphosphanylquinoxaline 、 (S)-tert-butylmethylphosphine-borane 在 四甲基乙二胺 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以720 mg的产率得到(R)-2-[(tert-butyl)(methyl)phosphino]-3-diphenylphosphinoquinoxaline
  参考文献：
  名称：

  OPTICALLY ACTIVE 2,3-BISPHOSPHINOPYRAZINE DERIVATIVE, METHOD FOR PRODUCING SAME, TRANSITION METAL COMPLEX, AND METHOD FOR PRODUCING ORGANIC BORON COMPOUND

  摘要：

  以下是一种光学活性的2,3-双膦吡嗪衍生物，由下列通式（1）所表示： 其中，R1代表从具有3个或更多碳原子的分支烷基，金刚烷基，可选取代的环烷基和可选取代的芳基中选择的基团；R2代表从具有3个或更多碳原子的分支烷基，金刚烷基和可选取代的环烷基中选择的基团，但当R1为叔丁基时，R1和R2不相同；R3代表一价取代基；n代表0到4之间的整数；*代表磷原子上的不对称中心。

  公开号：

  US20200377536A1
• 作为产物：
  描述：

  2,3-二氯喹喔啉 、 二苯基膦 在 palladium diacetate 作用下， 以 甲醇 、 氘代甲醇 为溶剂， 反应 2.0h， 生成 2-chloro-3-diphenylphosphanylquinoxaline 、 (3-chloroquinoxalin-2-yl)diphenylphosphine oxide
  参考文献：
  名称：

  Comparison of the reactivity of 2-amino-3-chloro- and 2,3-dichloroquinoxalines towards Ph2PH and Ph2PLi and of the properties of diphenylphosphanyl-quinoxaline P,N and P,P ligands

  摘要：

  The synthesis of quinoxaline P,N ligands by monoamination of 2,3-dichloroquinoxaline (1) to 2-amino-3-chloroquinoxalines 2a,b and the subsequent substitution of chlorine by a diphenylphosphanyl group was studied. Whereas the reaction of 2a,b with Ph2PH in the presence (or absence) of catalytic amounts of palladium acetate furnished only minor amounts of the expected ligands in favor of tetraphenyldiphosphane and dechlorinated quinoxalines, the coupling with Ph2PLi in ether provided the novel NH-functional P,N hybrid ligands 3a,b with a quinoxaline scaffold in moderate to good yields. 3a is slightly and 3b somewhat more sensitive to air oxidation, leading to the P-oxides 4a,b. The more reactive 1 forms with Ph2PH only a small amount of 2-chloro-3-diphenylphosphanylquinoxaline 5 and traces of the quinoxaline-bis(phosphane) 6. The main products are 2,2'-bis(quinoxaline) and Ph2PCl, which converts residual Ph2PH into tetraphenyldiphosphane. The coupling with Ph2PLi in diethyl ether, however, gave in a fast reaction high yields of 6, exceeding those of 3a,b, with interfering NH functions. Semi-empirical quantum chemical calculations (PM6) illuminate the background of the air sensitivity of 3a,b, whereas the recently reported 6 is air stable. Preliminary studies for use of the ligands in catalysis with the air-stable 6, showed moderate to good yields in the Pd-catalyzed C-N cross coupling of 2-bromopyridine with mesityl amine. Complex formation was confirmed by isolation of the Pd complex 7. The structure elucidation of the new compounds is based on conclusive NMR data and crystal structure analyses for 2b, 3a, 4a and 4b. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.089