2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide | 683749-05-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide
• 英文别名: 6,10,19,23-Tetratert-butyl-14-oxa-15lambda6-thiaheptacyclo[15.7.1.14,8.02,16.03,13.021,25.012,26]hexacosa-1(25),2(16),3(13),4(26),5,7,9,11,17,19,21,23-dodecaene 15,15-dioxide；6,10,19,23-tetratert-butyl-14-oxa-15λ6-thiaheptacyclo[15.7.1.14,8.02,16.03,13.021,25.012,26]hexacosa-1(25),2(16),3(13),4(26),5,7,9,11,17,19,21,23-dodecaene 15,15-dioxide
• CAS: 683749-05-5
• 化学式: C₄₀H₄₄O₃S
• 分子量: 604.854
• InChiKey: OMXPSMZDEOSMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide 以 硝基苯 为溶剂， 反应 20.0h， 以22%的产率得到4,5-bis[3,6-di(tert-butyl)-8-carboxynaphthyl]-2,7,10,13-tetra(tert-butyl)-acenaphtho[1,2-j]fluoranthene cyclic anhydride
  参考文献：
  名称：

  Unexpected conversion of a polycyclic thiophene to a macrocyclic anhydride

  摘要：

  Oxygenation of 2,5,9,12-tetra(tert-butyl)diacenaphtho[1,2-b: 1,2'-d]-thiophene (1, C40H44S) by peracids gave the cyclic sulfonic ester 4 (2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide, C40H44O3S) which, when heated in nitrobenzene, is converted into a complex, macrocyclic anhydride 3 (C80H88O3), which is derived from two molecules of 4. Further investigation found a likely intermediate in this reaction, 4,4,7,7'-tetra(tert-butyl)-1,1'-biacenaphthylenylidene-2,2'-dione (5, C40H44O2), apparently formed from 4 by additional oxidation. Anhydride 3 plausibly arises by Diels-Alder reaction of 4 and 5 followed by several ring fragmentations. The structures of 3, 4, and 5 were unambiguously established by X-ray crystallography. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2003.12.050
• 作为产物：
  描述：

  2,5,9,12-tetra(t-butyl)diacenaphtho[1,2-b:1',2'-d]thiophene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以20%的产率得到2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide
  参考文献：
  名称：

  Unexpected conversion of a polycyclic thiophene to a macrocyclic anhydride

  摘要：

  Oxygenation of 2,5,9,12-tetra(tert-butyl)diacenaphtho[1,2-b: 1,2'-d]-thiophene (1, C40H44S) by peracids gave the cyclic sulfonic ester 4 (2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide, C40H44O3S) which, when heated in nitrobenzene, is converted into a complex, macrocyclic anhydride 3 (C80H88O3), which is derived from two molecules of 4. Further investigation found a likely intermediate in this reaction, 4,4,7,7'-tetra(tert-butyl)-1,1'-biacenaphthylenylidene-2,2'-dione (5, C40H44O2), apparently formed from 4 by additional oxidation. Anhydride 3 plausibly arises by Diels-Alder reaction of 4 and 5 followed by several ring fragmentations. The structures of 3, 4, and 5 were unambiguously established by X-ray crystallography. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2003.12.050

文献信息

• Unexpected conversion of a polycyclic thiophene to a macrocyclic anhydride
  作者：Kathleen V Kilway、Keith A Lindgren、Joseph W Vincent、James A Watson、Robert G Clevenger、Robert D Ingalls、Douglas M Ho、Robert A Pascal

  DOI：10.1016/j.tet.2003.12.050

  日期：2004.3

  Oxygenation of 2,5,9,12-tetra(tert-butyl)diacenaphtho[1,2-b: 1,2'-d]-thiophene (1, C40H44S) by peracids gave the cyclic sulfonic ester 4 (2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1',2'-e]oxathiin 5,5-dioxide, C40H44O3S) which, when heated in nitrobenzene, is converted into a complex, macrocyclic anhydride 3 (C80H88O3), which is derived from two molecules of 4. Further investigation found a likely intermediate in this reaction, 4,4,7,7'-tetra(tert-butyl)-1,1'-biacenaphthylenylidene-2,2'-dione (5, C40H44O2), apparently formed from 4 by additional oxidation. Anhydride 3 plausibly arises by Diels-Alder reaction of 4 and 5 followed by several ring fragmentations. The structures of 3, 4, and 5 were unambiguously established by X-ray crystallography. (C) 2004 Published by Elsevier Ltd.