Dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide | 123434-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide
• 英文别名: Dinaphtho[2,1-d:1,2-f][1,3]dithiepine 3,3-dioxide；12λ6,14-dithiapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 12,12-dioxide
• CAS: 123434-96-8；135759-74-9
• 化学式: C₂₁H₁₄O₂S₂
• 分子量: 362.473
• InChiKey: ADYOKLQZMXCGOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.75h， 生成 2-(1-Phenyl-1-hydroxymethyl)dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide
  参考文献：
  名称：

  Asymmetric reactions of thioacetals and their S-oxides derived from 1,1'-binaphthalene-2,2'-dithiol

  摘要：

  The chiral dithiepine 3 was selectively oxidized to all possible oxides: the sulfoxide 9, the sulfone 16, the sulfone-sulfoxide 20, the disulfoxide 21, and the disulfone 22. The sulfinyl oxygens of 9, 14, 20, and 21 are always in the pseudoaxial configuration, as shown by the X-ray structure determination of 11a. Reaction of the anions of 3, 9, and 16 with methyl iodide, benzaldehyde, or acetophenone occurs efficiently. The stereoselectivity of the processes is high and maximized in sulfoxide 9, where the contributions of the chiral binaphthyl residue and the sulfoxide appear to occur synergistically. The alcohols derived from reaction of the anions of 3, 9, and 16 with benzaldehyde and acetophenone were also prepared in high yield and stereoselectivity via reduction or methylation of the phenyl ketone 8 and of its oxidized homologues 14 and 19. Alcohol 6a, prepared in 8:2 ratio in the reaction of 3 with benzaldehyde, was obtained as a single diastereoisomer in the reduction of 8 with lithium aluminum hydride.

  DOI：

  10.1021/jo00014a027
• 作为产物：
  描述：

  Dinaphtho<2,1-d:1',2'-f><1,3>dithiepine 在 potassium permanganate 、 间氯过氧苯甲酸 作用下， 生成 Dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide
  参考文献：
  名称：

  有机合成中的阻转异构硫化合物：二萘并[2,1- d：1'，2'- f ] [1,3]二硫平及其氧化物的碳负离子的产生和反应

  摘要：

  对二萘并[2,1- d：1'，2'- f ] [1,3]二硫平（2）进行氧化可得到单一的非对映异构亚砜（1），它与亲电试剂非对映特异性地反应，与未氧化的底物（2）和提供产物的非对映异构体混合物的氧化物（4），（6）和（7）的其他组合。

  DOI：

  10.1039/c39890000411

文献信息

• Atropisomeric sulphur compounds in organic synthesis: generation and reactions of the carbanions of dinaphtho[2,1-d:1′,2′-f][1,3]dithiepine and its oxides
  作者：Giovanna Delogu、Ottorino De Lucchi、Giulia Licini

  DOI：10.1039/c39890000411

  日期：——

  Oxidation of dinaphtho[2,1-d:1′,2′-f][1,3]dithiepine (2) gives a single diastereoisomeric sulphoxide (1) which reacts diastereospecifically with electrophiles at variance with the unoxidized substrate (2) and other combinations of oxides (4),(6), and (7) which afford diastereoisomeric mixtures of products.

  对二萘并[2,1- d：1'，2'- f ] [1,3]二硫平（2）进行氧化可得到单一的非对映异构亚砜（1），它与亲电试剂非对映特异性地反应，与未氧化的底物（2）和提供产物的非对映异构体混合物的氧化物（4），（6）和（7）的其他组合。
• DELOGU, GIOVANNA;DE, LUCCHI OTTORINO;LICINI, GIULIA, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 411-412
  作者：DELOGU, GIOVANNA、DE, LUCCHI OTTORINO、LICINI, GIULIA

  DOI：——

  日期：——
• Asymmetric reactions of thioacetals and their S-oxides derived from 1,1'-binaphthalene-2,2'-dithiol
  作者：Giovanna Delogu、Ottorino De Lucchi、Paola Maglioli、Giovanni Valle

  DOI：10.1021/jo00014a027

  日期：1991.7

  The chiral dithiepine 3 was selectively oxidized to all possible oxides: the sulfoxide 9, the sulfone 16, the sulfone-sulfoxide 20, the disulfoxide 21, and the disulfone 22. The sulfinyl oxygens of 9, 14, 20, and 21 are always in the pseudoaxial configuration, as shown by the X-ray structure determination of 11a. Reaction of the anions of 3, 9, and 16 with methyl iodide, benzaldehyde, or acetophenone occurs efficiently. The stereoselectivity of the processes is high and maximized in sulfoxide 9, where the contributions of the chiral binaphthyl residue and the sulfoxide appear to occur synergistically. The alcohols derived from reaction of the anions of 3, 9, and 16 with benzaldehyde and acetophenone were also prepared in high yield and stereoselectivity via reduction or methylation of the phenyl ketone 8 and of its oxidized homologues 14 and 19. Alcohol 6a, prepared in 8:2 ratio in the reaction of 3 with benzaldehyde, was obtained as a single diastereoisomer in the reduction of 8 with lithium aluminum hydride.