rac-(4aR,18aS)-2-((trimethylsilyl)oxy)-1,4,4a,18a-tetrahydrobenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocine 5,5,18,18-tetraoxide | 120546-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: rac-(4aR,18aS)-2-((trimethylsilyl)oxy)-1,4,4a,18a-tetrahydrobenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocine 5,5,18,18-tetraoxide
• CAS: 120546-21-6；132436-75-0
• 化学式: C₂₉H₂₈O₅S₂Si
• 分子量: 548.756
• InChiKey: PQIUOGACFXYUNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  37.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  rac-(4aR,18aS)-2-((trimethylsilyl)oxy)-1,4,4a,18a-tetrahydrobenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocine 5,5,18,18-tetraoxide 以 氯仿 为溶剂， 反应 24.0h， 以95%的产率得到3,4,4a,18a-tetrahydrobenzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dithiocin-2(1H)-one 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
• 作为产物：
  描述：

  2(1H)-喹喔啉酮,7-氟-3,4-二氢-3-甲基-(9CI) 在 sodium 、 对苯二酚 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 69.0h， 生成 rac-(4aR,18aS)-2-((trimethylsilyl)oxy)-1,4,4a,18a-tetrahydrobenzo[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