2,5-Bis-dodecyloxy-dibenzo[c,g]phenanthrene-7,10,11,14-tetraone | 142743-49-5

• 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: 2,5-Bis-dodecyloxy-dibenzo[c,g]phenanthrene-7,10,11,14-tetraone
• 英文别名: 2,5-Bis(dodecyloxy)dibenzo[c,g]phenanthrene-7,10,11,14-tetrone；10,15-didodecoxypentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(22),2,5,8,10,12,14,16,19-nonaene-4,7,18,21-tetrone
• CAS: 142743-49-5
• 化学式: C₄₆H₅₈O₆
• 分子量: 706.963
• InChiKey: YYSQBGJKQOPJAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  52
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-Bis-dodecyloxy-dibenzo[c,g]phenanthrene-7,10,11,14-tetraone 在 吡啶 、 氯化亚砜 、 氨基甲酸甲酯 作用下， 以 苯 为溶剂， 反应 12.0h， 以53%的产率得到2,5-Bis(dodecyloxy)[1,2,5]thiadiazolo[3'',4'':6',7']naphtho[1',2':5,6]phenanthro[2,3-c][1,2,5]thiadiazole-7,11,12,16-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：

  对苯二甲酸 在 aluminum oxide 、 titanocene dichloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 、 苯 为溶剂， 反应 164.0h， 生成 2,5-Bis-dodecyloxy-dibenzo[c,g]phenanthrene-7,10,11,14-tetraone
  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：——
• An Efficient Synthesis of Functionalized Helicenes
  作者：Thomas J. Katz、Longbin Liu、Nikolaos D. Willmore、Joseph M. Fox、Arnold L. Rheingold、Shuhao Shi、Colin Nuckolls、Barry H. Rickman

  DOI：10.1021/ja9721327

  日期：1997.10.1

  aromatic rings, give the corresponding helicenes in only low yields and low purities. [6]Helicenebisquinone 11c is resolved into its enantiomers. An X-ray diffraction analysis of the adduct of one of these enantiomers and l-prolinol shows the absolute stereochemistry of 11c and the regiochemistry with which the amine adds to the quinone.

  [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。
• Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them
  作者：Shuhao Shi、Thomas J. Katz、Bingwei V. Yang、Longbin Liu

  DOI：10.1021/jo00110a036

  日期：1995.3

  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.