2,3-di(((4-norborn-2-en-5-yl)methoxy)benzylthio)maleonitrile | 858284-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3-di(((4-norborn-2-en-5-yl)methoxy)benzylthio)maleonitrile
• 英文别名: (Z)-2,3-bis[[4-(2-bicyclo[2.2.1]hept-5-enylmethoxy)phenyl]methylsulfanyl]but-2-enedinitrile
• CAS: 858284-47-6
• 化学式: C₃₄H₃₄N₂O₂S₂
• 分子量: 566.788
• InChiKey: AXIXXTIPBZMLSA-YHZPTAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-2,3-dipropylmaleonitrile 、 2,3-di(((4-norborn-2-en-5-yl)methoxy)benzylthio)maleonitrile 在 magnesium di-n-butanolate 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 生成 2,3,7,8,12,13,17,18-octakis(propyl)-porphyrazinato magnesium(II) 、 magnesium;14,15-bis[[4-(2-bicyclo[2.2.1]hept-5-enylmethoxy)phenyl]methylsulfanyl]-4,5,9,10,19,20-hexapropyl-2,7,12,17,21,22-hexaza-23,24-diazanidapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaene
  参考文献：
  名称：

  ROM Polymerization−Capture−Release:  Application to the Synthesis of Unsymmetrical Porphyrazinedithiols and Peripherally Metalated Derivatives

  摘要：

  Crossover Linstead macrocyclization of a doubly norbornenyl-functionalized dimercaptornaleonitrile with dipropylmaleonitrile gave a crude mixture of porphyrazines containing the hexapropylpor-phyrazinedithiol magnesium complex. The mixture was subjected to ring-opening metathesis polymerization to yield the insoluble porphyrazinedithiol-functionalized polymers. Cleavage from the polymer backbone using mercury(II) acetate followed by reaction with electrophiles gave access to a range of thioporphyrazinedithiol derivatives including solitaire porphyrazines. Studies into the possible uses of hexapropyl-2,3-di-(carboxymethylthio)porphyrazine in sensing metal cations in solution are described.

  DOI：

  10.1021/jo050369c
• 作为产物：
  描述：

  5-(4-(hydroxymethyl)phenoxymethyl)bicyclo[2.2.1]hept-2-ene 在 氯化亚砜 、 三乙胺 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 18.5h， 生成 2,3-di(((4-norborn-2-en-5-yl)methoxy)benzylthio)maleonitrile
  参考文献：
  名称：

  ROM Polymerization−Capture−Release:  Application to the Synthesis of Unsymmetrical Porphyrazinedithiols and Peripherally Metalated Derivatives

  摘要：

  Crossover Linstead macrocyclization of a doubly norbornenyl-functionalized dimercaptornaleonitrile with dipropylmaleonitrile gave a crude mixture of porphyrazines containing the hexapropylpor-phyrazinedithiol magnesium complex. The mixture was subjected to ring-opening metathesis polymerization to yield the insoluble porphyrazinedithiol-functionalized polymers. Cleavage from the polymer backbone using mercury(II) acetate followed by reaction with electrophiles gave access to a range of thioporphyrazinedithiol derivatives including solitaire porphyrazines. Studies into the possible uses of hexapropyl-2,3-di-(carboxymethylthio)porphyrazine in sensing metal cations in solution are described.

  DOI：

  10.1021/jo050369c

文献信息

• ROM Polymerization−Capture−Release:  Application to the Synthesis of Unsymmetrical Porphyrazinedithiols and Peripherally Metalated Derivatives
  作者：Matthew J. Fuchter、Brian M. Hoffman、Anthony G. M. Barrett

  DOI：10.1021/jo050369c

  日期：2005.6.1

  Crossover Linstead macrocyclization of a doubly norbornenyl-functionalized dimercaptornaleonitrile with dipropylmaleonitrile gave a crude mixture of porphyrazines containing the hexapropylpor-phyrazinedithiol magnesium complex. The mixture was subjected to ring-opening metathesis polymerization to yield the insoluble porphyrazinedithiol-functionalized polymers. Cleavage from the polymer backbone using mercury(II) acetate followed by reaction with electrophiles gave access to a range of thioporphyrazinedithiol derivatives including solitaire porphyrazines. Studies into the possible uses of hexapropyl-2,3-di-(carboxymethylthio)porphyrazine in sensing metal cations in solution are described.