顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 | 333380-86-2

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷
• 英文名称: cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane
• 英文别名: Tedicyp；cis,cis,cis-1,2,3,4-Tetrakis[(diphenylphosphino)methyl]cyclopentane；diphenyl-[[(1R,2R,3S,4S)-2,3,4-tris(diphenylphosphanylmethyl)cyclopentyl]methyl]phosphane
• CAS: 333380-86-2
• 化学式: C₅₇H₅₄P₄
• 分子量: 862.951
• InChiKey: HYAJCBCVJRLTRN-BWULIGGSSA-N

物化性质

• 熔点：
  79℃

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以0.76 g的产率得到(1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphinoyl)methyl)cyclopentane
  参考文献：
  名称：

  A New Tetratertiary Phosphine Ligand and Its Use in Pd-Catalyzed Allylic Substitution

  摘要：

  A new tetraphosphine, the cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane(Tedicyp) 1 has been synthesized, characterized, and used in Pd-catalyzed allylic substitutions. The Tedicyp was easily prepared in seven steps from the commercially available himic anhydride. The structure of the complex Tedicyp-borane was determined by X-ray analysis. The tetraphosphine in combination with [Pd(eta (3)-C3H5)Cl](2) affords a very efficient catalyst for allylic substitution of several allylic acetates. Under mild conditions, very high turnover numbers and turnover frequencies have been obtained.

  DOI：

  10.1021/jo001146j
• 作为产物：
  描述：

  (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis(hydroxymethyl)cyclopentane 在 吡啶 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷
  参考文献：
  名称：

  A New Tetratertiary Phosphine Ligand and Its Use in Pd-Catalyzed Allylic Substitution

  摘要：

  A new tetraphosphine, the cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane(Tedicyp) 1 has been synthesized, characterized, and used in Pd-catalyzed allylic substitutions. The Tedicyp was easily prepared in seven steps from the commercially available himic anhydride. The structure of the complex Tedicyp-borane was determined by X-ray analysis. The tetraphosphine in combination with [Pd(eta (3)-C3H5)Cl](2) affords a very efficient catalyst for allylic substitution of several allylic acetates. Under mild conditions, very high turnover numbers and turnover frequencies have been obtained.

  DOI：

  10.1021/jo001146j
• 作为试剂：
  描述：

  4-溴苯酚 、 4-氟苯硼酸 在 bis(η3-allyl-μ-chloropalladium(II)) potassium carbonate 、 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 作用下， 以 xylene 为溶剂， 反应 24.0h， 以95%的产率得到4-氟-4'-羟基联苯
  参考文献：
  名称：

  钯-四膦催化芳基溴化物与芳基硼酸的交叉偶联：配体性质的显着影响

  摘要：

  cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane –[PdCl(C3H5)]2 体系催化芳基溴化物与芳基硼酸的交叉偶联，具有非常高的底物-催化剂比率和良好的收率；在该催化剂存在下，4-溴二苯甲酮与苯硼酸的加成反应可以得到 28000000 的转化次数。

  DOI：

  10.1039/b009520f

文献信息

• A New Tetratertiary Phosphine Ligand and Its Use in Pd-Catalyzed Allylic Substitution
  作者：Dorothée Laurenti、Marie Feuerstein、Gérard Pèpe、Henri Doucet、Maurice Santelli

  DOI：10.1021/jo001146j

  日期：2001.3.1

  A new tetraphosphine, the cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane(Tedicyp) 1 has been synthesized, characterized, and used in Pd-catalyzed allylic substitutions. The Tedicyp was easily prepared in seven steps from the commercially available himic anhydride. The structure of the complex Tedicyp-borane was determined by X-ray analysis. The tetraphosphine in combination with [Pd(eta (3)-C3H5)Cl](2) affords a very efficient catalyst for allylic substitution of several allylic acetates. Under mild conditions, very high turnover numbers and turnover frequencies have been obtained.