rac-(1R,4S,4aR,18aS)-1-methoxy-1,4,4a,18a-tetrahydro-1,4-epoxybenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocine 5,5,18,18-tetraoxide | 120546-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: rac-(1R,4S,4aR,18aS)-1-methoxy-1,4,4a,18a-tetrahydro-1,4-epoxybenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocine 5,5,18,18-tetraoxide
• CAS: 120546-23-8；132436-77-2
• 化学式: C₂₇H₂₀O₆S₂
• 分子量: 504.584
• InChiKey: XAJHLUZVQCKTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  35.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  Dinaphtho<2,1-d:1',2'-g><1,4>dithiocine 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.5h， 生成 rac-(1R,4S,4aR,18aS)-1-methoxy-1,4,4a,18a-tetrahydro-1,4-epoxybenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocine 5,5,18,18-tetraoxide
  参考文献：
  名称：

  Diels-Alder reactions of 1,2-(1,1'-binaphthalene-2,2'-diyldisulfonyl)ethylene with symmetrical and unsymmetrical dienes

  摘要：

  The C2-symmetrical chiral reagent 1,2-(1,1'-binaphthalene-2,2'-diyldisulfonyl)ethylene (1) is a reactive dienophile and forms Diels-Alder adducts with symmetrical and unsymmetrical dienes. In the case of unsymmetrical dienes the reaction affords, in most cases, a single diastereomeric adduct whose stereochemistry has been determined by NMR spectroscopy and confirmed by X-ray structure determination of selected adducts. The arylsulfonyl groups can be removed with formation of a double bond, making 1 a chiral synthetic equivalent of acetylene in [4 + 2]-cycloaddition reactions. The binaphthyl auxiliary can be recovered and recycled.

  DOI：

  10.1021/jo00005a041