4,4'-(((2s,4s)-1,3-di-tert-butyl-2,4-disulfido-1,3,2,4-diazadiphosphetidine-2,4-diyl)bis(oxy))dibenzaldehyde | 137918-44-6

• 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: 4,4'-(((2s,4s)-1,3-di-tert-butyl-2,4-disulfido-1,3,2,4-diazadiphosphetidine-2,4-diyl)bis(oxy))dibenzaldehyde
• CAS: 137918-44-6
• 化学式: C₂₂H₂₈N₂O₄P₂S₂
• 分子量: 510.555
• InChiKey: BZFRVWRZGLSKSB-RNPORBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenylthiophosphodi(methylhydrazide) 、 4,4'-(((2s,4s)-1,3-di-tert-butyl-2,4-disulfido-1,3,2,4-diazadiphosphetidine-2,4-diyl)bis(oxy))dibenzaldehyde 以 四氢呋喃 为溶剂， 反应 20.0h， 以60%的产率得到
  参考文献：
  名称：

  Design of new tools for macrocyclic synthesis. Applications to the preparation of polyphosphorus macrocycles

  摘要：

  New diphosphorus m,m' or p,p' dialdehydes 2-7 were prepared by treatment of 1,3-di-tert-butyldiaza-2,4-dichlorodiphosphetidine, 1, with 3- or 4-hydroxybenzaldehyde, and in the case of 4-7 in the presence of S8. These initial compounds when reacted with phosphodihydrazides RP(X) (NCH3NH2)2 9 and 10 allowed the preparation, via [2 + 2] cyclocondensation reactions, of macrocycles 11-13, 15, and 16 possessing six phosphorus atoms in the skeleton, different coordination modes (tri- or tetracoordinate) and both N-P-N and O-P-N linkages. Reaction of the tetraphosphorus dihydrazide 20 with 1,2-benzenedicarboxaldehyde gave macrocycle 22 with a total annular size of 29 ring atoms. Macrocycles 23 or 24 were obtained by reacting 20 with 2,6-pyridinedicarboxaldehyde or 1,3-benzenedicarboxaldehyde. Asymmetry can also be introduced via [1 + 1] cyclocondensation of tetraphosphorus dihydrazides 18 or 19 with diphosphorus dialdehydes 3 or 2; these reactions led to the 38-membered cyclic product 25. Two macrocycles 27, 28 incorporating five phosphorus atoms with three different types of phosphorus environments (C-P-C,N-P-N, and O-P-N) were obtained when tetraphosphorus dihydrazides 18 or 20 were reacted with the phosphorus dialdehyde 26. All the reactions were found stereospecific.

  DOI：

  10.1021/jo00029a034
• 作为产物：
  描述：

  在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 为溶剂， 反应 240.0h， 以84%的产率得到4,4'-(((2s,4s)-1,3-di-tert-butyl-2,4-disulfido-1,3,2,4-diazadiphosphetidine-2,4-diyl)bis(oxy))dibenzaldehyde
  参考文献：
  名称：

  Design of new tools for macrocyclic synthesis. Applications to the preparation of polyphosphorus macrocycles

  摘要：

  New diphosphorus m,m' or p,p' dialdehydes 2-7 were prepared by treatment of 1,3-di-tert-butyldiaza-2,4-dichlorodiphosphetidine, 1, with 3- or 4-hydroxybenzaldehyde, and in the case of 4-7 in the presence of S8. These initial compounds when reacted with phosphodihydrazides RP(X) (NCH3NH2)2 9 and 10 allowed the preparation, via [2 + 2] cyclocondensation reactions, of macrocycles 11-13, 15, and 16 possessing six phosphorus atoms in the skeleton, different coordination modes (tri- or tetracoordinate) and both N-P-N and O-P-N linkages. Reaction of the tetraphosphorus dihydrazide 20 with 1,2-benzenedicarboxaldehyde gave macrocycle 22 with a total annular size of 29 ring atoms. Macrocycles 23 or 24 were obtained by reacting 20 with 2,6-pyridinedicarboxaldehyde or 1,3-benzenedicarboxaldehyde. Asymmetry can also be introduced via [1 + 1] cyclocondensation of tetraphosphorus dihydrazides 18 or 19 with diphosphorus dialdehydes 3 or 2; these reactions led to the 38-membered cyclic product 25. Two macrocycles 27, 28 incorporating five phosphorus atoms with three different types of phosphorus environments (C-P-C,N-P-N, and O-P-N) were obtained when tetraphosphorus dihydrazides 18 or 20 were reacted with the phosphorus dialdehyde 26. All the reactions were found stereospecific.

  DOI：

  10.1021/jo00029a034