4,4'-biphenanthro<4,3-e;3',4'-g>-1,4-dithiocine

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4,4'-biphenanthro<4,3-e;3',4'-g>-1,4-dithiocine
• 英文别名: 4,4'-biphenanthro[4,3-e;3',4'-g]-1,4-dithiocine
• 化学式: C₃₀H₁₈S₂
• 分子量: 442.605
• InChiKey: ATNPYSWJBNEMMX-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.85
• 重原子数：
  32.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4'-biphenanthro<4,3-e;3',4'-g>-1,4-dithiocine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以80%的产率得到4,4'-biphenanthro<4,3-e;3',4-g>-1,4-dithiocine 1,1,4,4-tetraoxide
  参考文献：
  名称：

  New axially chiral sulfur compounds: Synthesis and conformational stability of enantiopure 4,4′-biphenanthrene-3,3′-dithiol and related atropisomeric derivatives

  摘要：

  Enantiopure (R)- and (S)-4,4'-biphenanthrene-3,3'-dithiol la has been prepared for the first time through a synthetic procedure involving in the key step a stereoconservative Newman-Kwart thermorearrangement of the bis-N,N-dimethylthiocarbamoyl ester of(R)- and (S)-biphenanthrol 2b, respectively. The atropisomeric conformations of la are not interconverted even at temperatures as high as 285 degrees C, whereas the related biphenanthrothiophene 3 is completely racemized in a few minutes at 250 degrees C. The axially chiral backbone of la has been incorporated in a set of novel C-2 symmetry sulfur reagents suitable for a variety of stereoselective reactions.

  DOI：

  10.1016/0957-4166(95)00074-y
• 作为产物：
  描述：

  顺-1,2-二氯乙烯 、 2-(4-丁一氧代丁氧基)乙醇 在 sodium 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以90%的产率得到4,4'-biphenanthro<4,3-e;3',4'-g>-1,4-dithiocine
  参考文献：
  名称：

  New axially chiral sulfur compounds: Synthesis and conformational stability of enantiopure 4,4′-biphenanthrene-3,3′-dithiol and related atropisomeric derivatives

  摘要：

  Enantiopure (R)- and (S)-4,4'-biphenanthrene-3,3'-dithiol la has been prepared for the first time through a synthetic procedure involving in the key step a stereoconservative Newman-Kwart thermorearrangement of the bis-N,N-dimethylthiocarbamoyl ester of(R)- and (S)-biphenanthrol 2b, respectively. The atropisomeric conformations of la are not interconverted even at temperatures as high as 285 degrees C, whereas the related biphenanthrothiophene 3 is completely racemized in a few minutes at 250 degrees C. The axially chiral backbone of la has been incorporated in a set of novel C-2 symmetry sulfur reagents suitable for a variety of stereoselective reactions.

  DOI：

  10.1016/0957-4166(95)00074-y

文献信息

• New axially chiral sulfur compounds: Synthesis and conformational stability of enantiopure 4,4′-biphenanthrene-3,3′-dithiol and related atropisomeric derivatives
  作者：Antonio Dore、Davide Fabbri、Serafino Gladiali、Giovanni Valle

  DOI：10.1016/0957-4166(95)00074-y

  日期：1995.3

  Enantiopure (R)- and (S)-4,4'-biphenanthrene-3,3'-dithiol la has been prepared for the first time through a synthetic procedure involving in the key step a stereoconservative Newman-Kwart thermorearrangement of the bis-N,N-dimethylthiocarbamoyl ester of(R)- and (S)-biphenanthrol 2b, respectively. The atropisomeric conformations of la are not interconverted even at temperatures as high as 285 degrees C, whereas the related biphenanthrothiophene 3 is completely racemized in a few minutes at 250 degrees C. The axially chiral backbone of la has been incorporated in a set of novel C-2 symmetry sulfur reagents suitable for a variety of stereoselective reactions.