1-Phenyl-3-{phenyl-[(E)-p-tolylimino]-methyl}-thiourea | 94078-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Phenyl-3-{phenyl-[(E)-p-tolylimino]-methyl}-thiourea
• 英文别名: (1Z)-1-[(4-methylanilino)-phenylmethylidene]-3-phenylthiourea
• CAS: 94078-44-1
• 化学式: C₂₁H₁₉N₃S
• 分子量: 345.468
• InChiKey: NPYVUVPRNJDEHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Phenyl-3-{phenyl-[(E)-p-tolylimino]-methyl}-thiourea 在 吡啶 、 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以91%的产率得到Phenyl-[2-phenyl-3-p-tolyl-2H-[1,2,4]thiadiazol-(5E)-ylidene]-amine; hydrobromide
  参考文献：
  名称：

  Synthesis and Structure of Some 6,7-Dihydro-thiazolo[4,5- d ][1,3,2]diaza-λ 5 -phosphorines

  摘要：

  1,2,4-Thiadiazol-5(2H)-imines 1 react with malononitrile under ring cleavage cycloaddition and subsequent ring rearrangement. The products 2 incorporate the enaminonitrile fragment. Treatment of compounds 2 with phosphorus pentachloride results in thiazolo[4,5-d][1,3,2]diaza-lambda(5)-phosphorine derivatives 3 with a reactive chloro, substituent in position 2 and 4 which can be substituted by various nucleophiles. The structure of the trimethoxy derivative 7c was determined by an X-ray structure analysis.

  DOI：

  10.1080/713744577
• 作为产物：
  描述：

  N-(p-Tolyl)benzimidoylisothiocyanat 、 苯胺 以 丙酮 为溶剂， 反应 1.0h， 生成 1-Phenyl-3-{phenyl-[(E)-p-tolylimino]-methyl}-thiourea
  参考文献：
  名称：

  N-芳基氨基-1：3-二氮杂-1：3-丁二烯与乙烯酮的合成和区域选择性[4 + 2]环加成/亲核反应及伴随的重排

  摘要：

  N-Arylamino-1：3-diaza-1：3-butadienes 4与苯基和氯乙烯酮发生区域选择性反应，导致3-芳基-2-甲基硫代6-苯基-4（3H）-嘧啶酮7的高收率。经由叠氮鎓中间体12与溴和碘酮的类似反应，以高收率产生了3-芳基-S-（N-芳基氨基）-2-甲硫基-6-苯基4（3H）-嘧啶酮13，环加成反应的机理还报道了这些二氮杂丁二烯的​​半经验AM1计算结果。

  DOI：

  10.1016/0040-4020(95)00372-f

文献信息

• Unusual Reactivity of 2,3-diphenylcyclopropenone towards <i>N</i>-imidoylthioureas; Facile Synthesis of 3-aryl-2,5,6-triphenylpyrimidin-4(3<i>H</i>)-one (PART III)
  作者：Ashraf A. Aly、Ahmed M. NourEl-Din、Moshen A.-M. Gomaa、Alan B. Brown、Magda S. Fahmi

  DOI：10.3184/030823407x234563

  日期：2007.8

  2,3-Diphenylcyclopropenone (1) reacts with N-imidoylthioureas 2a–e to form the pyrimidin-4(3 H)-ones 5a–e. The reaction mechanism can be described as due to stepwise addition accompanied by elimination of phenyl isothiocyanate.

  2,3-Diphenylcyclopropenone (1) 与 N-imidoylthioureas 2a-e 反应生成嘧啶-4(3H)-酮 5a-e。反应机理可描述为逐步加成并伴随着异硫氰酸苯酯的消除。
• Facile Synthesis of 4-phenyl-6-[(Z)phenylimino]-3,6-dihydro-1,3,5-thiadiazine-2,2-dicarbonitriles
  作者：Ashraf A. Aly、Kamal M. El-Shaieb

  DOI：10.3184/030823407x207086

  日期：2007.4

  N-Imidoylthioureas 2a–e reacted with 1,1,2,2-tetracyanoethylene (1) to form the thiadiazines 3a–e. In the case of 1e, tricyanovinylation of a phenyl substituent accompanied formation of the thiadiazine ring.

  N-Imidoylthioureas 2a-e 与 1,1,2,2-四氰基乙烯（1）反应生成噻二嗪类化合物 3a-e。在 1e 的情况中，苯基取代基的三氰基乙炔化伴随着噻二嗪环的形成。
• Reaction of <i>N</i>-imidoylthioureas with Dimethyl Acetylenedicarboxylate: Synthesis of new 1,3,5-thiadiazepines
  作者：Ashraf A. Aly、Kamal M. El-Shaieb

  DOI：10.3184/030823407x255579

  日期：2007.10

  The reaction of N-imidoylthioureas 2a–e with dimethyl acetylenedicarboxylate (DMAD, 1) led unexpectedly to the 1,3,5-thiadiazepines 6a–e. The mechanism of the reaction is discussed.

  N-亚氨酰硫脲 2a-e 与乙炔二甲酸二甲酯 (DMAD, 1) 的反应出人意料地导致了 1,3,5-硫氮卓类 6a-e。讨论了反应机理。
• 2,3-Diaryl-5-anilino[1,2,4]thiadiazoles as melanocortin MC4 receptor agonists and their effects on feeding behavior in rats
  作者：Kevin Pan、Malcolm K Scott、Daniel H.S Lee、Louis J Fitzpatrick、Jeffery J Crooke、Ralph A Rivero、Daniel I Rosenthal、Anil H Vaidya、Boyu Zhao、Allen B Reitz

  DOI：10.1016/s0968-0896(02)00428-5

  日期：2003.1

  The melanocortin-4 receptor (MC4) modulates physiological functions such as feeding behavior, nerve regeneration, and drug addiction. Using a high throughput screen based on I-121-NDP-MSH binding to the human MC4 receptor, we discovered 2,3-diaryl-5-anilino[1,2,4]thiadiazoles 3 as potent and selective MC4 receptor agonists. Through SAR development on the three attached aryl rings, we improved the binding affinity from 174 nM to 4.4 nM IC50. When delivered intraperitoneally, compounds 3a, 3b, and 3c induced significant inhibition of food intake in a fasting-induced feeding model in rats. When delivered orally, these compounds lost activity, mainly due to rapid metabolism to inactive imidoylthiourea reduction products. (C) 2002 Elsevier Science Ltd. All rights reserved.
• One-Pot Synthesis of 2-Aryl-3-phenyl(benzyl)-5-phenylimino-Δ⁴-1,2,4-thiadiazolines using<i>N</i>-Chlorosuccinimide
  作者：J. P. Chetia、S. N. Mazumder、M. P. Mahajan

  DOI：10.1055/s-1985-31118

  日期：——