(1RS,2RS)-2-(2-cyanopropan-2-yl)acenaphthen-1-yl dithiobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1RS,2RS)-2-(2-cyanopropan-2-yl)acenaphthen-1-yl dithiobenzoate
• 英文别名: [(1R,2R)-2-(2-cyanopropan-2-yl)-1,2-dihydroacenaphthylen-1-yl] benzenecarbodithioate
• 化学式: C₂₃H₁₉NS₂
• 分子量: 373.543
• InChiKey: VRXCPMDGYNETPJ-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (1RS,2RS)-2-(2-cyanopropan-2-yl)acenaphthen-1-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91%的产率得到2-acenaphthen-1-yl-2-methylpropionitrile
  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：

  苊烯 、 2-氰丙基-2-基苯并二硫 在 偶氮二异丁腈 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以83%的产率得到(1RS,2RS)-2-(2-cyanopropan-2-yl)acenaphthen-1-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

文献信息

• Synthesis and Fluorescence of a Series of Multichromophoric Acenaphthenyl Compounds
  作者：Ming Chen、Kenneth P. Ghiggino、San H. Thang、Jonathan White、Gerard J. Wilson

  DOI：10.1021/jo047899d

  日期：2005.3.1

  [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.