(1SR,2SR,1'RS,2'RS)-2'-(2-cyanopropan-2-yl)-1,2,1',2'-tetrahydro[1,1']biacenaphthylen-2-yl dithiobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1SR,2SR,1'RS,2'RS)-2'-(2-cyanopropan-2-yl)-1,2,1',2'-tetrahydro[1,1']biacenaphthylen-2-yl dithiobenzoate
• 英文别名: [(1S,2R)-2-[(1S,2R)-2-(2-cyanopropan-2-yl)-1,2-dihydroacenaphthylen-1-yl]-1,2-dihydroacenaphthylen-1-yl] benzenecarbodithioate
• 化学式: C₃₅H₂₇NS₂
• 分子量: 525.738
• InChiKey: XSDMUULSLKGSCI-JDIHBLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1SR,2SR,1'RS,2'RS)-2'-(2-cyanopropan-2-yl)-1,2,1',2'-tetrahydro[1,1']biacenaphthylen-2-yl dithiobenzoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 氯苯 为溶剂， 反应 4.0h， 以84%的产率得到(1RS,2RS,1'RS)-2-methyl-2-(1,2,1',2'-tetrahydro[1,1']biacenaphthylen-2-yl)propionitrile
  参考文献：
  名称：

  Synthesis and Fluorescence of a Series of Multichromophoric Acenaphthenyl Compounds

  摘要：

  [GRAPHICS]A novel free radical trapping reaction based on a stepwise radical reversible addition-fragmentation mechanism has been utilized to synthesize a series of acenaphthenyl dimers and trimers. The synthetic procedure involves the reaction of acenaphthylene with dithiobenzoate compounds (S=C(Ph)-SR) in the presence of a free radical initiator followed by reduction of the dithiobenzoyl end group with tributyltin hydride. Stereoisomers of the compounds have been isolated and their structures determined by proton NMR and X-ray crystallography. The solution fluorescence of the compounds has been characterized to reveal the requirements for intramolecular excimer (excited-state dimer) formation. Only in compounds containing identical stereochemical arrangements of adjacent acenaphthenyl groups is excimer fluorescence observed following photoexcitation.

  DOI：

  10.1021/jo047899d
• 作为产物：
  描述：

  (1RS,2RS)-2-(2-cyanopropan-2-yl)acenaphthen-1-yl dithiobenzoate 、 苊烯 在 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以10%的产率得到(1SR,2SR,1'RS,2'RS)-2'-(2-cyanopropan-2-yl)-1,2,1',2'-tetrahydro[1,1']biacenaphthylen-2-yl dithiobenzoate
  参考文献：
  名称：

  Synthesis and Fluorescence of a Series of Multichromophoric Acenaphthenyl Compounds

  摘要：

  [GRAPHICS]A novel free radical trapping reaction based on a stepwise radical reversible addition-fragmentation mechanism has been utilized to synthesize a series of acenaphthenyl dimers and trimers. The synthetic procedure involves the reaction of acenaphthylene with dithiobenzoate compounds (S=C(Ph)-SR) in the presence of a free radical initiator followed by reduction of the dithiobenzoyl end group with tributyltin hydride. Stereoisomers of the compounds have been isolated and their structures determined by proton NMR and X-ray crystallography. The solution fluorescence of the compounds has been characterized to reveal the requirements for intramolecular excimer (excited-state dimer) formation. Only in compounds containing identical stereochemical arrangements of adjacent acenaphthenyl groups is excimer fluorescence observed following photoexcitation.

  DOI：

  10.1021/jo047899d