2-(1,2-bis(diphenylphosphanyl)ethyl)pyridine | 1387578-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(1,2-bis(diphenylphosphanyl)ethyl)pyridine
• 英文别名: 1,1'-[1-(2-pyridyl)-1,2-ethanediyl]bis(1,1-diphenylphosphine)；(2-Diphenylphosphanyl-1-pyridin-2-ylethyl)-diphenylphosphane；(2-diphenylphosphanyl-1-pyridin-2-ylethyl)-diphenylphosphane
• CAS: 1387578-81-5
• 化学式: C₃₁H₂₇NP₂
• 分子量: 475.51
• InChiKey: CDNWXJRNEHOOKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1,2-bis(diphenylphosphanyl)ethyl)pyridine 在 双氧水 作用下， 反应 1.0h， 生成 (1-(pyridin-2-yl)ethane-1,2-diyl)bis(diphenylphosphine oxide)
  参考文献：
  名称：

  在炔烃上依次向膦中添加膦，以在催化下选择性合成1,2-二膦基乙烷。定义明确的NHC铜磷酸盐与原位CuCl2 / NHC催化剂

  摘要：

  The well-defined NHC-copper phosphides [(NHC)CuPPh2](3) (1, NHC = 1,3-diisopropy1-4,5-dimethyli- midazol-2-ylidene (I'Pr); 2, NHC = N,N-di-tert-butylimidazol-2-ylidene ((IBu)-Bu-t)) have been prepared by the reaction of simple copper halides with HPPh2 in the presence of N-heterocyclic carbenes (NHCs). Complexes 1 and 2 enabled catalytic double hydrophosphination of alkyl and aryl terminal alkynes to yield 1,2-diphosphinoethanes selectively in good yields. On the basis of these results, the most efficient and pratical in situ CuCl2/NHC catalyst has been developed. It catalyzes the selective double hydrophosphination of the alkynes with high efficiency and a wide substrate scope and exhibits even better performance than the well-defined NHC-Cu phosphides. The mechanistic studies disclosed that the formation of a copper acetylide in the catalytic cycle played an important role in the acceleration of the catalytic process.

  DOI：

  10.1021/acs.organomet.6b00854
• 作为产物：
  描述：

  2-乙炔基吡啶 、 二苯基膦 在 cyclopentadienyl iron(II) dicarbonyl dimer 作用下， 以 neat (no solvent) 为溶剂， 反应 16.0h， 以86%的产率得到2-(1,2-bis(diphenylphosphanyl)ethyl)pyridine
  参考文献：
  名称：

  使用市售铁化合物对末端炔烃进行可见光和热驱动的双氢磷酸化反应

  摘要：

  市售的铁化合物，[CpFe的量（CO）2 ] 2（1）（CP =η 5 -C 5 H ^ 5），是用于与二苯基膦可见光照射或热的条件下末端芳炔烃组成的双hydrophosphination一个有效的催化剂与文献报道相比，某些底物的反应时间缩短了两个数量级。在这些反应中产生的1,2-双（二苯基膦基）乙烷产物很容易以高收率分离。

  DOI：

  10.1039/c8cc00847g

文献信息

• Regioselective Double Hydrophosphination of Terminal Arylacetylenes Catalyzed by an Iron Complex
  作者：Masahiro Kamitani、Masumi Itazaki、Chihiro Tamiya、Hiroshi Nakazawa

  DOI：10.1021/ja304818c

  日期：2012.7.25

  The first catalytic double hydrophosphination of alkynes was achieved by reaction with diarylphosphines in the presence of an iron catalyst. The double hydrophosphination proceeded regioselectively and effectively for various secondary arylphosphines and terminal alkynes to give 1,2-bisphosphinoethane derivatives.

  炔烃的第一次催化双氢膦化反应是通过在铁催化剂存在下与二芳基膦反应实现的。双氢膦化反应对各种仲芳基膦和末端炔烃进行区域选择性和有效的反应，得到 1,2-双膦基乙烷衍生物。
• Double hydrophosphination of alkynes promoted by rhodium: the key role of an N-heterocyclic carbene ligand
  作者：Andrea Di Giuseppe、Roberto De Luca、Ricardo Castarlenas、Jesús J. Pérez-Torrente、Marcello Crucianelli、Luis A. Oro

  DOI：10.1039/c5cc09156j

  日期：——

  The stereoelectronic properties of the NHC ligand make possible the rhodium-catalysed double hydrophosphination of alkynes avoiding the catalyst deactivation by the diphosphine product.

  NHC配体的立体电子性质使铑催化炔烃的双氢磷酸化避免了二膦产物使催化剂失活。
• Visible-light and thermal driven double hydrophosphination of terminal alkynes using a commercially available iron compound
  作者：Brandon J. Ackley、Justin K. Pagano、Rory Waterman

  DOI：10.1039/c8cc00847g

  日期：——

  A commercially available iron compound, [CpFe(CO)2]2 (1) (Cp = η5-C5H5), is an efficient catalyst for the double hydrophosphination of terminal aryl alkynes with diphenylphosphine under visible light irradiation or thermal conditions with a reduction of reaction times of up to two orders of magnitude for some substrates over literature reports. The 1,2-bis(diphenylphosphino)ethane products generated

  市售的铁化合物，[CpFe的量（CO）2 ] 2（1）（CP =η 5 -C 5 H ^ 5），是用于与二苯基膦可见光照射或热的条件下末端芳炔烃组成的双hydrophosphination一个有效的催化剂与文献报道相比，某些底物的反应时间缩短了两个数量级。在这些反应中产生的1,2-双（二苯基膦基）乙烷产物很容易以高收率分离。
• Sequential Addition of Phosphine to Alkynes for the Selective Synthesis of 1,2-Diphosphinoethanes under Catalysis. Well-Defined NHC-Copper Phosphides vs in Situ CuCl₂/NHC Catalyst
  作者：Jia Yuan、Lizhao Zhu、Jianying Zhang、Jianfeng Li、Chunming Cui

  DOI：10.1021/acs.organomet.6b00854

  日期：2017.1.23

  The well-defined NHC-copper phosphides [(NHC)CuPPh2](3) (1, NHC = 1,3-diisopropy1-4,5-dimethyli- midazol-2-ylidene (I'Pr); 2, NHC = N,N-di-tert-butylimidazol-2-ylidene ((IBu)-Bu-t)) have been prepared by the reaction of simple copper halides with HPPh2 in the presence of N-heterocyclic carbenes (NHCs). Complexes 1 and 2 enabled catalytic double hydrophosphination of alkyl and aryl terminal alkynes to yield 1,2-diphosphinoethanes selectively in good yields. On the basis of these results, the most efficient and pratical in situ CuCl2/NHC catalyst has been developed. It catalyzes the selective double hydrophosphination of the alkynes with high efficiency and a wide substrate scope and exhibits even better performance than the well-defined NHC-Cu phosphides. The mechanistic studies disclosed that the formation of a copper acetylide in the catalytic cycle played an important role in the acceleration of the catalytic process.