N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide

• 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-[(4-diphenylphosphinophenyl)methyl] D-gluconamide
• 英文别名: N-(4-Diphenyl-phosphino)phenylmethyl gluconamide；N-(4-diphenylphosphinophenyl)methyl gluconamide；(2R,3S,4R,5R)-N-[(4-diphenylphosphanylphenyl)methyl]-2,3,4,5,6-pentahydroxyhexanamide
• 化学式: C₂₅H₂₈NO₆P
• 分子量: 469.474
• InChiKey: NMNOKKGJPKHDQU-JLLPCOHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(diphenylphosphino)benzonitrile 在 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.5h， 生成 N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide
  参考文献：
  名称：

  Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands

  摘要：

  Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2'-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2'-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)(2) and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)(3) (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)(2) (0.001 mol%) and 10 (0.002 mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00576-8
• 作为试剂：
  描述：

  4-溴代联苯 、 4-甲苯硼酸 在 PdCl₂(GLCAphos)2 potassium phosphate 、 N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide 作用下， 以 水 为溶剂， 反应 16.0h， 以99%的产率得到1-甲基-4-(4-苯基苯基)苯
  参考文献：
  名称：

  Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands

  摘要：

  Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2'-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2'-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)(2) and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)(3) (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)(2) (0.001 mol%) and 10 (0.002 mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00576-8

文献信息

• Triphenylphosphine derivative, production process therefor, palladium complex thereof, and process for producing biaryl derivative
  申请人：——

  公开号：US20030065208A1

  公开（公告）日：2003-04-03

  Provided are a novel triphenyl phosphine derivative synthesized from a triphenylphosphine and a hydroxy-containing lactone; a palladium and a nickel complexes comprising the derivative as a ligand; and a process for preparing a biaryl derivative using the complex as a catalyst. A product can be easily separated from a catalyst or a phosphorus compound, and biaryl derivative can be synthesized in a higher yield, by using the complex of the present invention as a catalyst.

  提供了一种新型的三苯基膦衍生物，通过三苯基膦和含羟基的内酯合成；一种以该衍生物为配体的钯和镍配合物；以及一种利用该配合物作为催化剂制备联苯衍生物的方法。通过使用本发明的复合物作为催化剂，产品可以很容易地与催化剂或磷化合物分离，联苯衍生物可以以更高的产率合成。
• TRIPHENYLPHOSPHINE DERIVATIVE, PRODUCTION PROCESS THEREFOR, PALLADIUM COMPLEX THEREOF, AND PROCESS FOR PRODUCING BIARYL DERIVATIVE
  申请人：Mitsubishi Rayon Co., Ltd.

  公开号：EP1270582A1

  公开（公告）日：2003-01-02

  Provided are a novel triphenyl phosphine derivative synthesized from a triphenylphosphine and a hydroxy-containing lactone; a palladium and a nickel complexes comprising the derivative as a ligand; and a process for preparing a biaryl derivative using the complex as a catalyst. A product can be easily separated from a catalyst or a phosphorus compound, and biaryl derivative can be synthesized in a higher yield, by using the complex of the present invention as a catalyst.

  本发明提供了一种由三苯基膦和含羟基内酯合成的新型三苯基膦衍生物；一种以该衍生物为配体的钯和镍配合物；以及一种以该配合物为催化剂制备双芳基衍生物的工艺。使用本发明的配合物作为催化剂，产物可以很容易地从催化剂或磷化合物中分离出来，并且可以以更高的产率合成双芳基衍生物。
• Ueda, Masato; Nishimura, Masato; Miyaura, Norio, Synlett, 2000, # 6, p. 856 - 858
  作者：Ueda, Masato、Nishimura, Masato、Miyaura, Norio

  DOI：——

  日期：——
• TRIPHENYLPHOSPHINE DERIVATIVES, PALLADIUM OR NICKEL COMPLEXES THEREOF, AND PROCESS FOR PREPARING BIARYL DERIVATIVES
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP1270582B1

  公开（公告）日：2006-08-30
• US6693210B2
  申请人：——

  公开号：US6693210B2

  公开（公告）日：2004-02-17