1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-bis(2-butoxyethoxy)[6]helicene | 142719-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-bis(2-butoxyethoxy)[6]helicene
• 英文别名: 6,11-Bis(2-butoxyethoxy)hexahelicene-1,4,13,16-tetrone
• CAS: 142719-84-4
• 化学式: C₃₈H₃₆O₈
• 分子量: 620.699
• InChiKey: PMTPQAQZGUXLRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-bis(2-butoxyethoxy)[6]helicene 在 吡啶 、 氧氯化硒 、 氨基甲酸甲酯 作用下， 以 苯 为溶剂， 反应 20.0h， 以72%的产率得到13,21-Bis(2-butoxyethoxy)-7,27-diselena-6,8,26,28-tetrazaoctacyclo[15.15.0.02,14.03,11.05,9.020,32.023,31.025,29]dotriaconta-1(17),2,5,8,11,13,15,18,20,22,25,28,31-tridecaene-4,10,24,30-tetrone
  参考文献：
  名称：

  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them

  摘要：

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.

  DOI：

  10.1021/jo00110a036
• 作为产物：
  描述：

  2,7-diacetylnaphthalene 在 氢氧化钾 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 93.0h， 生成 1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-bis(2-butoxyethoxy)[6]helicene
  参考文献：
  名称：

  功能化螺旋的有效合成

  摘要：

  [5]-和[6]螺旋烯双醌可以通过将1,4-二乙酰苯或2,7-二乙酰萘的烯醇醚与对苯醌组合而容易且大量制备。类似的二乙烯基芳烃要么没有醚官能团，要么没有连接到双键上，而是连接到芳环上，只能以低产率和低纯度得到相应的螺旋。[6] Helicenebisquinone 11c 被拆分成它的对映异构体。这些对映异构体之一和 l-脯氨醇的加合物的 X 射线衍射分析显示了 11c 的绝对立体化学和胺与醌加成的区域化学。

  DOI：

  10.1021/ja9721327

文献信息

• Willmore, Nikolaos D.; Liu, Longbin; Katz, Thomas J., Angewandte Chemie, 1992, vol. 104, # 8, p. 1081 - 1082
  作者：Willmore, Nikolaos D.、Liu, Longbin、Katz, Thomas J.

  DOI：——

  日期：——
• Synthesis of Helical Conjugated Ladder Polymers
  作者：Yujia Dai、Thomas J. Katz

  DOI：10.1021/jo9622284

  日期：1997.3.1

  The synthesis is described of the first helical ladder polymers with unbroken pathways of conjugation that extend not only through each monomeric unit, but between them as well. The key step is the condensation of 1,2-phenylenediamine and a transition metal salt with a helicene having salicylaldehyde's functionality at both ends. This gives rise to ''metal salophen'' units that bind adjacent helicenes, provide conjugated links from one ring system to the next, and constrain the p-orbitals of the rings they unite to be nearly parallel. Because the helicene monomers are enantiopure, so too are the polymeric structures to which they give rise. One of the polymers (6) winds continuously in only one direction. Another (4a) winds in one direction through the helicene moieties and in the other direction through the metal-salophens. The circular dichroisms of the former at wavelengths near 600 nm are notably large. The corresponding circular dichroisms of the latter are much smaller. MALDI-TOF mass spectra provide particularly strong evidence for the structures assigned. The polymers are very soluble in a variety of organic solvents and seem to have number average molecular weights of ca. 7000.
• Dai, Yujia; Katz, Thomas J.; Nichols, David A., Angewandte Chemie, 1996, vol. 108, # 18, p. 2230 - 2232
  作者：Dai, Yujia、Katz, Thomas J.、Nichols, David A.

  DOI：——

  日期：——