(S)-2-methyldinaphtho[2,1-d:1',2'-f]-[1,3]dithiepine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-methyldinaphtho[2,1-d:1',2'-f]-[1,3]dithiepine
• 英文别名: 13-Methyl-12,14-dithiapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
• 化学式: C₂₂H₁₆S₂
• 分子量: 344.501
• InChiKey: YHRLMALAWFHGSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯苯甲醛 、 (S)-2-methyldinaphtho[2,1-d:1',2'-f]-[1,3]dithiepine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (S_a,R)-2-methyl-2-{1-(4'-chlorophenyl)-1-hydroxymethyl}dinaphtho[2,1-d:1',2'-f]-[1,3]dithiepine 、 (S_a,S)-2-methyl-2-{1-(4'-chlorophenyl)-1-hydroxymethyl}dinaphtho[2,1-d:1',2'-f]-[1,3]dithiepine
  参考文献：
  名称：

  醛与光学活性二硫缩醛的不对称亲核加成反应及其在光学活性α-羟基酮合成中的应用

  摘要：

  通过缩醛与具有手性联萘骨架的二硫醇 (1) 反应制备光学活性二硫缩醛。各种醛与锂化二硫代缩醛的不对称加成反应顺利进行，以非对映体过量提供相应的手性醇 (4) 和 (5)。此外，通过去除4a的手性助剂制备光学纯的α-羟基酮是在没有消旋化的情况下实现的。

  DOI：

  10.3987/com-02-9516
• 作为产物：
  描述：

  2(1H)-喹喔啉酮,7-氟-3,4-二氢-3-甲基-(9CI) 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 (S)-2-methyldinaphtho[2,1-d:1',2'-f]-[1,3]dithiepine
  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

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：——