ethyl phenyl[(E)-1-octen-2-yl]phosphinate

• 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: ethyl phenyl[(E)-1-octen-2-yl]phosphinate
• 英文别名: [Ethoxy(oct-1-en-2-yl)phosphoryl]benzene
• 化学式: C₁₆H₂₅O₂P
• 分子量: 280.347
• InChiKey: VQOXKBMPYVEOLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-辛炔 、 ethyl Phenylphosphinate 在 palladium(II)(diphenylphosphinic acid(-2H)) 、 1,3-双(二苯基膦)丙烷 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以97%的产率得到ethyl phenyl[(E)-1-octen-2-yl]phosphinate
  参考文献：
  名称：

  A new oxapalladacycle generated via ortho C–H activation of phenylphosphinic acid: an efficient catalyst for Markovnikov-type additions of E–H bonds to alkynes

  摘要：

  一种新的氧钯环3可以通过将二苯膦酸与乙酸钯直接进行邻位钯化便捷地制备。由3衍生的催化剂能够高效催化E–H键（P(O)–H、S–H和spC–H）向炔烃的马克尼科夫型加成反应，且具有独特的催化循环。

  DOI：

  10.1039/c0cc03436c

文献信息

• Efficient and Selective Nickel-Catalyzed Addition of H−P(O) and H−S Bonds to Alkynes
  作者：Li-Biao Han、Chen Zhang、Hideaki Yazawa、Shigeru Shimada

  DOI：10.1021/ja0494297

  日期：2004.4.28

  metal catalysts in the catalytic additions of a variety of P(O)-H bonds and an S-H bond to alkynes, affording regio- and stereoselectively both the Markovnikov and the anti-Markovnikov adducts, respectively, in high yields. A related five-coordinate hydrido nickel complex in the catalysis is successfully isolated, which can react readily with an alkyne to give the addition products.

  廉价的镍催化剂在催化加成各种 P(O)-H 键和 SH 键到炔烃时比相应的贵金属催化剂更具反应性，提供区域和立体选择性的马尔科夫尼科夫和反马尔科夫尼科夫加合物，分别以高产。催化剂中相关的五配位氢化镍配合物被成功分离，它可以很容易地与炔烃反应生成加成产物。
• A new oxapalladacycle generated via ortho C–H activation of phenylphosphinic acid: an efficient catalyst for Markovnikov-type additions of E–H bonds to alkynes
  作者：Qing Xu、Ruwei Shen、Yutaka Ono、Ritsuko Nagahata、Shigeru Shimada、Midori Goto、Li-Biao Han

  DOI：10.1039/c0cc03436c

  日期：——

  A new oxapalladacycle 3 can be conveniently prepared via direct ortho palladation of diphenylphosphinic acid with palladium acetate. Catalysts derived from 3 can efficiently catalyze Markovnikov-type additions of E–H bonds (P(O)–H, S–H and spC–H) to alkynesvia a unique catalytic cycle.

  一种新的氧钯环3可以通过将二苯膦酸与乙酸钯直接进行邻位钯化便捷地制备。由3衍生的催化剂能够高效催化E–H键（P(O)–H、S–H和spC–H）向炔烃的马克尼科夫型加成反应，且具有独特的催化循环。
• Palladium-catalysed regioselective addition reaction of ethyl phenylphosphinate with terminal acetylenes: ligand- and solvent-dependent regioselectivity
  作者：Satish Kumar Nune、Masato Tanaka

  DOI：10.1039/b703165c

  日期：——

  Palladium-1,2-bis(diphenylphosphino)ethane complex catalyses regioselective Markovnikov addition of ethyl phenylphosphinate to terminal alkynes in toluene, while the use of tri-tert-butylphosphine as the ligand or ethanol as the solvent leads to regioselectivity reversal.

  1,2,2-双（二苯基膦基）乙烷钯配合物催化苯基次膦酸乙酯向甲苯中的末端炔烃的区域选择性马尔科夫尼科夫加成反应，而使用三叔丁基膦作为配体或乙醇作为溶剂会导致区域选择性的逆转。
• Process for preparation of alkenylphosphine oxides or alkenylphosphinic esters
  申请人：——

  公开号：US20040059146A1

  公开（公告）日：2004-03-25

  A novel process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters provided by which the objective compounds can be easily, safely and efficiently synthesized and easily separated and purified with little formation of by-products. Specifically, a process of conducting the addition reaction of an easily available secondary phosphine oxide or hydrogen phosphinic acid ester with an acetylene compound with a catalyst containing a Group 9 or 10 metal of the periodic table to thereby obtain the corresponding alkenylphosphine oxide or alkenylphosphinic acid ester.

  一种制备烯基膦氧化物或烯基膦酸酯的新型工艺，通过该工艺可以轻松、安全、高效地合成目标化合物，并且很容易分离和纯化，副产物生成量很少。具体来说，该工艺是将易得的二次膦氧化物或氢膦酸酯与乙炔化合物在含有周期表第9或第10族金属的催化剂的作用下进行加成反应，从而获得相应的烯基膦氧化物或烯基膦酸酯。
• PROCESS FOR PREPARATION OF ALKENYLPHOSPHINE OXIDES OR ALKENYLPHOSPHINIC ACID ESTERS
  申请人：Japan Science and Technology Agency

  公开号：EP1369422B1

  公开（公告）日：2008-07-23