1,4-bis(diphenylphosphino)-1,2,3,4-tetraphenyl-1,3-butadiene | 348582-86-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,4-bis(diphenylphosphino)-1,2,3,4-tetraphenyl-1,3-butadiene
• 英文别名: (1,2,3,4-Tetraphenylbuta-1,3-diene-1,4-diyl)bis(diphenylphosphane)；(4-diphenylphosphanyl-1,2,3,4-tetraphenylbuta-1,3-dienyl)-diphenylphosphane
• CAS: 348582-86-5
• 化学式: C₅₂H₄₀P₂
• 分子量: 726.837
• InChiKey: HTCHLXAATFQBFG-UHFFFAOYSA-N

物化性质

• 沸点：
  816.2±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-bis(diphenylphosphino)-1,2,3,4-tetraphenyl-1,3-butadiene 在 sodium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 δ-[(1,4-bis(diphenylphosphino)-1,2,3,4-tetraphenyl-1,3-butadiene)Pt((S)-BINOL)]
  参考文献：
  名称：

  Comparative Study of Diastereoisomer Interconversion in Chiral BINOL-ate and Diamine Platinum Complexes of Conformationally Flexible NUPHOS Diphosphines

  摘要：

  A thorough and detailed study of diastereointerconversion in the chiral platinum complexes [(NUPHOS)Pt{(S)-BINOL}] (3a-e) has been undertaken and compared with the results of a similar study with [(BIPHEP)Pt{(S)-BINOL}]. Rate data revealed that this process obeys first-order relaxation kinetics, and rate constants for conversion of the minor to the major diastereoisomer have been obtained. Eyring analysis of the data gave DeltaH(double dagger) and DeltaS(double dagger) values of 22-25 kcal mol(-1) and -1 to -16 eu, respectively. In combination with computational analysis, these studies indicate that atropinversion most likely occurs via an on-metal pathway involving a planar seven-membered transition state. Substitution of (S)-BINOL for (S,S)-DPEN results in a marked reduction in the barrier to atropinversion; a DeltaH(double dagger) value of 17 kcal mol(-1) has been determined for the conversion of delta-[(Ph-4-NUPHOS)Pt{(S,S)-DPEN}]Cl-2 to lambda-[(Ph-4-NUPHOS)Pt{(S,S)-DPEN}]Cl-2, which could indicate that an alternative mechanism operates.

  DOI：

  10.1021/om034289f
• 作为试剂：
  描述：

  溴苯 、 仲丁基氯化镁 在 1,4-bis(diphenylphosphino)-1,2,3,4-tetraphenyl-1,3-butadiene 、 palladium dichloride 作用下， 以 乙醚 、 癸烷 为溶剂， 反应 0.08h， 生成 仲丁基苯
  参考文献：
  名称：

  锆介导的新型1,4-双（二苯基膦基）-1,3-丁二烯桥联二膦，NUPHOS：用于钯介导的交叉偶联的高效催化剂。

  摘要：

  DOI：

  10.1021/ja010090n

文献信息

• [EN] METHOD FOR PRODUCING AMIDINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS D'AMIDINE
  申请人：BIOCRYST PHARM INC

  公开号：WO2016029216A2

  公开（公告）日：2016-02-25

  The invention provides methods and intermediates useful in the synthesis of a compound of formula (I): or a pharmaceutically acceptable salt, solvate, ester or prodrug thereof; wherein the variables are as defined herein.

  本发明提供了用于合成式(I)化合物的方法和中间体，或其药学上可接受的盐、溶剂和前药酯；其中变量如本文所定义。
• Zirconium-Mediated Synthesis of a New Class of 1,4-Bis(diphenylphosphino)-1,3-butadiene-Bridged Diphosphine, NUPHOS:  Highly Efficient Catalysts for Palladium-Mediated Cross Couplings
  作者：Simon Doherty、Julian G. Knight、Edward G. Robins、Tom H. Scanlan、Paul A. Champkin、William Clegg

  DOI：10.1021/ja010090n

  日期：2001.5.1
• Comparative Study of Diastereoisomer Interconversion in Chiral BINOL-ate and Diamine Platinum Complexes of Conformationally Flexible NUPHOS Diphosphines
  作者：Simon Doherty、Colin R. Newman、Rakesh K. Rath、Jan-Albert van den Berg、Christopher Hardacre、Mark Nieuwenhuyzen、Julian G. Knight

  DOI：10.1021/om034289f

  日期：2004.3.1

  A thorough and detailed study of diastereointerconversion in the chiral platinum complexes [(NUPHOS)Pt(S)-BINOL}] (3a-e) has been undertaken and compared with the results of a similar study with [(BIPHEP)Pt(S)-BINOL}]. Rate data revealed that this process obeys first-order relaxation kinetics, and rate constants for conversion of the minor to the major diastereoisomer have been obtained. Eyring analysis of the data gave DeltaH(double dagger) and DeltaS(double dagger) values of 22-25 kcal mol(-1) and -1 to -16 eu, respectively. In combination with computational analysis, these studies indicate that atropinversion most likely occurs via an on-metal pathway involving a planar seven-membered transition state. Substitution of (S)-BINOL for (S,S)-DPEN results in a marked reduction in the barrier to atropinversion; a DeltaH(double dagger) value of 17 kcal mol(-1) has been determined for the conversion of delta-[(Ph-4-NUPHOS)Pt(S,S)-DPEN}]Cl-2 to lambda-[(Ph-4-NUPHOS)Pt(S,S)-DPEN}]Cl-2, which could indicate that an alternative mechanism operates.