dinaphtho<2,1-e:1',2'-g><1,4>dithiocine 1,1,4,4-tetraoxide | 120546-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dinaphtho<2,1-e:1',2'-g><1,4>dithiocine 1,1,4,4-tetraoxide
• 英文别名: (13Z)-12lambda6,15lambda6-dithiapentacyclo[14.8.0.02,11.03,8.019,24]tetracosa-1(16),2(11),3,5,7,9,13,17,19,21,23-undecaene 12,12,15,15-tetraoxide；(13Z)-12λ6,15λ6-dithiapentacyclo[14.8.0.02,11.03,8.019,24]tetracosa-1(16),2(11),3,5,7,9,13,17,19,21,23-undecaene 12,12,15,15-tetraoxide
• CAS: 120546-24-9
• 化学式: C₂₂H₁₄O₄S₂
• 分子量: 406.483
• InChiKey: BVTJAVNOGFHDIO-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dinaphtho<2,1-e:1',2'-g><1,4>dithiocine 1,1,4,4-tetraoxide 在 对苯二酚 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 64.0h， 生成 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：

  Dinaphtho<2,1-d:1',2'-g><1,4>dithiocine 在 oxydat, reagent 作用下， 生成 dinaphtho<2,1-e:1',2'-g><1,4>dithiocine 1,1,4,4-tetraoxide
  参考文献：
  名称：

  Cossu, Sergio; Delogu, Giovanna; Lucchi, Ottorino De, Angewandte Chemie, 1989, vol. 101, # 6, p. 767 - 768

  摘要：

  DOI：

文献信息

• Cycloadditions of vinylindoles with chiral carbodienophiles: the first asymmetric Diels-Alder reactions in the vinylhetarane series
  作者：Ulf Pindur、Gundula Lutz、Gudrun Fischer、Dieter Schollmeyer、Werner Massa、Ludger Schröder

  DOI：10.1016/s0040-4020(01)80385-9

  日期：1993.4

  The first asymmetric Diels-Alder reactions of some 3- and 2-vinylindoles with (N-propenoyl)bomane-10,2-sultam are described. With one exception, the experimental results are indicative of a high pi-facial diastereoselectivity. Following a related procedure, 3-vinylindoles were also allowed to react with a racemic bis(naphthylsulfonyl)-dienophile to furnish tetrahydrocarbazoles with endo-diastereoselectivity.
• Diels-Alder reactions of 1,2-(1,1'-binaphthalene-2,2'-diyldisulfonyl)ethylene with symmetrical and unsymmetrical dienes
  作者：Ottorino De Lucchi、Davide Fabbri、Sergio Cossu、Giovanni Valle

  DOI：10.1021/jo00005a041

  日期：1991.3

  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.
• Cossu, Sergio; Delogu, Giovanna; Lucchi, Ottorino De, Angewandte Chemie, 1989, vol. 101, # 6, p. 767 - 768
  作者：Cossu, Sergio、Delogu, Giovanna、Lucchi, Ottorino De、Fabbri, Davide、Licini, Giulia

  DOI：——

  日期：——