(C4NH4)O2OC(O)(CH2)2C(O)NH(C6H3)(CH2PPh2)2 | 631898-28-7

• 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: (C4NH4)O2OC(O)(CH2)2C(O)NH(C6H3)(CH2PPh2)2
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 4-[3,5-bis(diphenylphosphanylmethyl)anilino]-4-oxobutanoate
• CAS: 631898-28-7
• 化学式: C₄₀H₃₆N₂O₅P₂
• 分子量: 686.684
• InChiKey: ROONBRVKFDYXPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  palladium(II) trifluoroacetate 、 (C4NH4)O2OC(O)(CH2)2C(O)NH(C6H3)(CH2PPh2)2 以 四氢呋喃 为溶剂， 生成 ((C4NH4)O2OC(O)(CH2)2C(O)NH(C6H2)(CH2PPh2)2)Pd(trifluoroacetate)
  参考文献：
  名称：

  The first synthesis of stable palladium(II) PCP-type catalysts supported on silica—application to the Heck reaction

  摘要：

  An efficient method for the formation of a silica-immobilized tridentate diphosphinoaryl ligand (PCP-type) palladium(II) complex (11) is described and successfully used as a catalyst for the Heck reaction. Commercially available 5-amino-isophthalic acid dimethyl ester was converted to N-acetyl-3,5-bis(chloromethyl)aniline (4) in three steps, by reduction, acetylation, and chlorination (Scheme 1). Arbuzov reaction of 4 led to the diphosphine oxide (5). Deprotection and functional group manipulations allowed the transformation of 5 into N-[3,5-bis-(diphenyl-phosphinoylmethyl)-phenyl]-succinamic acid (7). Subsequent reduction of 7 with HSiCl3 afforded the diphosphine (8) attached to silica by transforming compound 8 to N-{3,5-bis[(diphenyl-phosphanyl)methyl]-phenyl}-succinamic acid 2,5-dioxo-pyrrolidin-1-yl ester (9). Palladium(II) trifluoroacetate was used to form the PCP-type palladium(II) complex. This complex shows high catalytic activity in the Heck reaction for aryl iodides, and it is also active with aryl bromides. The catalyst is thermally stable and it is also stable towards oxygen and moisture. In addition, it can be recycled by simple filtration in air and reused with moderate loss of activity. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1381-1169(03)00158-4
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-[3,5-bis(diphenylphosphanyl-methyl)phenyl]succinamic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (C4NH4)O2OC(O)(CH2)2C(O)NH(C6H3)(CH2PPh2)2
  参考文献：
  名称：

  硅胶上负载的可回收三齿稳定钯（II）PCP型催化剂用于内酯的选择性合成

  摘要：

  使用固定在二氧化硅（A）和二氧化硅上的三齿二膦基芳基配体（PCP型）钯（II）催化剂，通过2-烯丙基苯酚的环羰基化反应，以良好的选择性和高收率合成了五元​​或七元环内酯。支持的树枝状聚合物（B，C和D）。这些固定化的催化剂具有很高的活性，可以通过在空气中简单过滤而再循环，并且仅在中等程度的活性损失的情况下重复使用，结合了非均相催化剂和均相催化剂的优势。这些配合物对氧气和湿气也很稳定。

  DOI：

  10.1002/adsc.200404109