bis(3-dimethylaminophenyl)disulfide | 705964-31-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis(3-dimethylaminophenyl)disulfide
• 英文别名: 3-[[3-(dimethylamino)phenyl]disulfanyl]-N,N-dimethylaniline
• CAS: 705964-31-4
• 化学式: C₁₆H₂₀N₂S₂
• 分子量: 304.48
• InChiKey: HDOXFXSOACZJSR-UHFFFAOYSA-N

物化性质

• 沸点：
  162-166 °C(Press: 16 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(3-dimethylaminophenyl)disulfide 在 盐酸 、 甲酸 、 硫化氢 作用下， 生成 2-amino-5-dimethylamino-phenyl mercaptan
  参考文献：
  名称：

  Zincke; Mueller, Chemische Berichte, 1913, vol. 46, p. 783

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 bis(3-dimethylaminophenyl)disulfide
  参考文献：
  名称：

  Zincke; Mueller, Chemische Berichte, 1913, vol. 46, p. 783

  摘要：

  DOI：

文献信息

• Novel chalcogenoxanthylium dyes for purging blood pathogens and for photodynamic therapy
  申请人：Detty R. Michael

  公开号：US20060040908A1

  公开（公告）日：2006-02-23

  Provided are chalcogenoxanthylium compounds which can effectively be used as sensitizers in photodynamic therapy, virucides in photodynamic antimicrobial chemotherapy and reversal agents of Pgp function in cancer cells. Further provided is a general method for the preparation of chalcogenoxanthylium compounds.

  提供了硫、硒和碲氧杂芴阳离子化合物，可有效用作光动力疗法的增敏剂、光动力抗微生物化疗的病毒灭活剂以及癌细胞Pgp功能的逆转剂。还提供了一种制备硫、硒和碲氧杂芴阳离子化合物的通用方法。
• A Microwave-Assisted Synthesis of Julolidine-9-carboxamide Derivatives and Their Conversion to Chalcogenoxanthones via Directed Metalation
  作者：Jason J. Holt、Brandon D. Calitree、Josiah Vincek、Michael K. Gannon、Michael R. Detty

  DOI：10.1021/jo070086f

  日期：2007.3.1

  7-tetramethyljulolidine gave the corresponding N-piperidine tetramethyljulolidine-9-thioamide. The thioamides were converted to the corresponding carboxamides with trifluoroacetic anhydride. The amide group directed ortho-metalation in the julolidine system, but not in the tetramethyljulolidine system. The resulting anion was captured by dichalcogenide electrophiles. The resulting products were converted to chalcogenoxanthones

  通过微波辅助的Willgerodt-Kindler反应将9-甲酰基甲氧萘啶氧化为N-哌啶或N-吗啉朱螺啶-9-硫酰胺。9-甲酰基-1,1,7,7-四甲基甲氧萘啶得到相应的N-哌啶四甲基甲氧吡啶-9-硫酰胺。用三氟乙酸酐将硫代酰胺转化为相应的羧酰胺。酰胺基团在聚ul啶体系中定向原位金属化，但不在四甲基聚ul啶体系中。生成的阴离子被二卤化原电子亲电试剂捕获。用三氯氧磷和三乙胺（POCl 3 / Et 3 N）将所得产物转化为硫属黄嘌呤。
• Synthesis, properties, and photodynamic properties in vitro of heavy-chalcogen analogues of tetramethylrosamine
  作者：Michael R Detty、Paras N Prasad、David J Donnelly、Tymish Ohulchanskyy、Scott L Gibson、Russell Hilf

  DOI：10.1016/j.bmc.2004.03.029

  日期：2004.5

  Thio and seleno analogues of tetramethylrosamine were prepared by the directed-metalation/cyclization of the corresponding N,N-diethyl 2-(3-dimethylaminophenylchalcogeno)-4-dimethylaminobenzamide to the 2,7-bis-(N,N-dimethylaniiiio)-9H-chalcoaenoxanthen-9-one followed by the addition of phenylmagnesium bromide, dehydration, and ion exchange to the chloride salt. The thio and seleno tetramethylrosamines had longer wavelengths of absorption and higher quantum yields for the generation of singlet oxygen than tetramethylrosamine. Both the thio and selenoanalogues of tetramethylrosamine were efficient photosensitizers against R3230AC rat mammary adenocarcinoma cells in vitro. (C) 2004 Elsevier Ltd. All rights reserved.
• Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)
  作者：Alexandra Orchard、Gregory A. Schamerhorn、Brandon D. Calitree、Geri A. Sawada、Tip W. Loo、M. Claire Bartlett、David M. Clarke、Michael R. Detty

  DOI：10.1016/j.bmc.2012.05.075

  日期：2012.7

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.
• Longer-Wavelength-Absorbing, Extended Chalcogenorhodamine Dyes
  作者：Mark W. Kryman、Theresa M. McCormick、Michael R. Detty

  DOI：10.1021/acs.organomet.6b00255

  日期：2016.6.13

  Extended rhodamines were prepared by inserting an additional fused benzene ring into the rhodamine xanthylium core. The synthesis of "bent" dyes 4-E (E = S, Se, Te) began with regioselective lithiation of the 1-position of N,N-diisopropyl 6-dimethylamino-2-naphthamide (11b) with n-BuLi/TMEDA (>= 25:1 1- vs 3-lithiation) followed by addition of a dichalcogenide electrophile. The synthesis of "linear" dyes 5-E (E = S, Se, Te) began with regioselective lithiation of the 3-position of N,N-diethyl 6-dimethylamino-2-naphthamide (11a) with lithium tetramethylpiperidide (>= 50:1 3- vs 1-lithiation) followed by addition of a dichalcogenide electrophile. Dyes 4-E and 5-E have absorption maxima in the 633-700 nm range. Dyes 4-E generate singlet oxygen upon irradiation while dyes 4-S and 5-S are highly fluorescent, with quantum yields for fluorescence of 0.47 and 0.18, respectively. DFT calculations were performed on the 4-E and 5-E chromophores. For the dyes 4-E, the lowest energy excitation is due solely to the HOMO-LUMO transition. For dyes 5-E, the lowest energy excitation is a combination of two excitations, both having contributions from the HOMO to LUMO and HOMO-1 to LUMO.