2-(1-Phenyl-1-hydroxymethyl)dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide | 135696-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-Phenyl-1-hydroxymethyl)dinaphtho<2,1-d:1',2'-f><1,3>dithiepine S,S-dioxide
• 英文别名: (S)-[(13S)-12,12-dioxo-12lambda6,14-dithiapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl]-phenylmethanol；(S)-[(13S)-12,12-dioxo-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-decaen-13-yl]-phenylmethanol
• CAS: 135696-97-8；135759-76-1；135759-77-2；135759-78-3
• 化学式: C₂₈H₂₀O₃S₂
• 分子量: 468.597
• InChiKey: WDKSIEQKLMEJBA-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Dinaphtho<2,1-d:1',2'-f><1,3>dithiepine 在 potassium permanganate 、 lithium aluminium tetrahydride 、 正丁基锂 、 magnesium sulfate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 7.75h， 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

文献信息

• 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.