N-{Phenyl-[(E)-p-tolylimino]-methyl}-piperidine-1-carboximidothioic acid methyl ester | 128652-32-4

• 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: N-{Phenyl-[(E)-p-tolylimino]-methyl}-piperidine-1-carboximidothioic acid methyl ester
• CAS: 128652-32-4
• 化学式: C₂₁H₂₅N₃S
• 分子量: 351.516
• InChiKey: BNGLWDXYGWKPON-JKZRTEGISA-N

物化性质

• 沸点：
  500.1±43.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-{Phenyl-[(E)-p-tolylimino]-methyl}-piperidine-1-carboximidothioic acid methyl ester 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2,3-diphenyl-9-thia-1,4a-diazafluoren-4-one
  参考文献：
  名称：

  新型杂环稠合的1,3-二氮杂丁-1,3-二烯的合成及其在与烯酮的环加成反应中的重排：杂环稠合的嘧啶酮衍生物的合成

  摘要：

  1,3- diazabuta-1,3-二烯反应1与2-氨基苯硫酚已经显示出导致优异的产率ñ -苯并噻唑-2-基- Ñ ' -芳基苯甲脒2。他们的区域选择性与各种烯酮的[4 + 2]环加成反应显示出新型的苯并噻唑并嘧啶酮4。描述了合成双硫代取代的1,3-二氮杂丁-1,3-二烯8和9的相似且方便的方案，以及伴随其[4 + 2]环加成与许多烯酮的有趣重排。

  DOI：

  10.1016/j.tet.2004.02.023
• 作为产物：
  描述：

  苯并-p-甲苯胺 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 生成 N-{Phenyl-[(E)-p-tolylimino]-methyl}-piperidine-1-carboximidothioic acid methyl ester
  参考文献：
  名称：

  Amidine derived 1,3-diazabuta-1,3-dienes as potential antibacterial and antifungal agents

  摘要：

  Several 1-aryl-2-phenyl-4-piperidino-4-thioalkyl-1,3-diazabuta-1,3-dienes were prepared by the treatment of N-arylimino isothiocyanate with piperidine followed by S-alkylation with alkyl iodides in the presence of dry acetone and potassium hydroxide. The constitution of the products was supported by IR, PMR and mass spectral study. The compounds synthesized were tested in in vitro against E coli, S. aureus, P. aeruginosa, B. cereus and B. subtilis and fungal stains, Candida albicans and Aspergillus niger. Standard drugs were also tested under identical conditions for comparing the results. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.104

文献信息

• Reactions of 1,3-diaza-1,3-butadienes with haloketenes - rearrangements accompanying [4+2] cycloaddition reactions.
  作者：Sujit N. Mazumdar、Sucharita Mukherjee、Arun K. Sharma、Devashish Sengupta、Mohinder P. Mahajan

  DOI：10.1016/s0040-4020(01)90485-5

  日期：——

  1-Aryl-2-phenyl-4-thioalkyl-4-secondaryamino-1,3-diaza-1, 3-butadienes 8 yielded interesting pyrimidones 10, 22 and 7 with chloroketenes 2, 11 and 12 through their episulfonium intermediates, whereas 1-aryl-2-phenyl-(methylthio) -4-dimethylamino-1,3-diaza-1,3-butadienes 1 give different pyrimidones with different haloketenes (chloro, bromo and iodo).

  1-芳基-2-苯基-4-硫代-4- secondaryamino -1,3-二氮杂-1,3-丁二烯8名产生了有趣的嘧啶酮10，22和7与chloroketenes 2，11和12通过它们的episulfonium中间体，而1 -芳基-2-苯基-（甲硫基）-4-二甲基氨基-1,3-二氮杂-1,3-丁二烯1生成具有不同卤代烯（氯代，溴代和碘代）的不同嘧啶酮。
• Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: synthesis of pyrimidinone derivatives
  作者：Arun K. Sharma、S. Jayakumar、Maninder S. Hundal、Mohinder P. Mahajan

  DOI：10.1039/b109922c

  日期：2002.3.8

  The reactions of 4-dialkylamino substituted 1,3-diazabuta-1,3-dienes 1 with butadienylketene 2, are shown to undergo [4 + 2] cycloadditions to yield 5-(buta-1′,3′-dienyl)pyrimidinone 4 and tandem [1,5]H and [1,5]SCH3 shifts are shown to accompany the [4 + 2] cycloaddition reactions of 4-dialkylamino-4-methylthio substituted 1,3-diazabuta-1,3-dienes 5 with 2. The regioselective reactions of N-arylamino-1,3-diazabuta-1,3-dienes 11 and 14 with butadienylketene 2 are reported to yield 5-(buta-1′,3′-dienyl)-2-dialkylaminopyrimidin-4(3H)-one 13 and a mixture of 5-(buta-1′,3′-dienyl)-2-methylthiopyrimidin-4(3H)-one 17, 2-methylthio-5-[1′-(N-phenylamino)but-2′-enyl]pyrimidin-4(3H)-one 19 and 2-methylthio-5-[3′-(N-phenylamino)but-1′-enyl]pyrimidin-4(3H)-one 20, respectively. Tandem [1,5]H, [1,3]NHPh and [1,5]NHPh shifts are involved in the formation of pyrimidinones 19 and 20. The Diels–Alder reactions of the 5-dienylpyrimidinones with dimethyl acetylenedicarboxylate (DMAD) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) yielded corresponding cycloadducts.

  4- 二烷基氨基取代的 1,3-二氮杂吲哚-1,3-二烯 1 与丁二烯酮 2 发生[4 + 2]环加成反应，生成 5-(丁-1′、3′-二烯基）嘧啶酮 4，并显示 4-二烷基氨基-4-甲硫基取代的 1,3-二氮杂-1,3-二烯 5 与 2 的[4 + 2]环加成反应伴随着串联[1,5]H 和[1,5]SCH3 迁移。据报道，N-芳基氨基-1,3-二氮杂吲哚-1,3-二烯 11 和 14 与丁二烯基酮 2 发生了区域选择性反应，生成了 5-(丁-1′,3′-二烯基)-2-二烷基氨基嘧啶-4(3H)-酮 13 和 5-(丁-1′,3′-二烯基)-2-二烷基氨基嘧啶-4(3H)-酮的混合物、3′-二烯基）-2-甲硫基嘧啶-4(3H)-酮 17、2-甲硫基-5-[1′-(N-苯基氨基)丁-2′-烯基]嘧啶-4(3H)-酮 19 和 2-甲硫基-5-[3′-(N-苯基氨基)丁-1′-烯基]嘧啶-4(3H)-酮 20 的混合物。[1,5]H、[1,3]NHPh 和 [1,5]NHPh 串联转变参与了嘧啶酮 19 和 20 的形成。5-二烯基嘧啶酮与乙炔二甲酸二甲酯（DMAD）和 4-苯基-1,2,4-三唑啉-3,5-二酮（PTAD）的 Diels-Alder 反应生成了相应的环加载产物。
• [4+2] cycloaddition reactions of various 1,3-diaza-1.3-Butadienes with ketenes
  作者：Sujit N. Mazumdar、Mohinder P. Mahajan

  DOI：10.1016/s0040-4020(01)86423-1

  日期：1991.1

  [4+2] cycloaddition reactions of 1-aryl-4-dimethylainino-1,3-diaza-1, 3-butadienes (), 1 -aryl-4-dimethylamino-2-methylthio-1, 3-diaza-1, 3-butadienes (), 1-aryl-4-methylthio-2-phenyl-4-sec. amino-1, 3-diaza-1, 3-butadienes () and 4, 4-bis(sec.amino)-1,2-diphenyl-1, 3-diaza-1, 3-butadienes () with monophenyiketene and similar cycloaddition reactions of , and with monochloroketene are described.

  1-芳基-4-二甲基氨基ino-1,3-diaza-1、3-丁二烯（），1-芳基-4-二甲基氨基-2-甲硫基-1、3-diaza-1，[4 + 2]的环加成反应3-丁二烯（），1-芳基-4-甲硫基-2-苯基-4-秒。氨基-1，3-二氮杂-1，3-丁二烯（）和4，4-双（仲氨基）-1,2-二苯基-1，3-二氮杂-1，3-丁二烯（）与单苯乙酮和类似物的环加成反应，和与monochloroketene中描述。
• Unusual methylene transfer in reactions of Simmons–Smith reagent with 1,3-diazabuta-1,3-dienes: synthesis of functionalised imidazole derivatives
  作者：S Jayakumar、Mohinder P Mahajan

  DOI：10.1016/s0040-4020(02)00127-8

  日期：2002.4

  The reactions of Simmons–Smith reagent with 1-aryl-2-phenyl-4-methylthio-4-secondary amino 1,3-diazabuta-1,3-dienes 1 underwent an unusual 1,4-methylene transfer resulting in the formation of 1-aryl-2-phenyl-4-secondary amino imidazoles 4. Whereas, its reactions with 1-aryl-2-phenyl-4-secondary amino-1,3-diazabuta-1,3-dienes 8 underwent an initial 1,2-methylene transfer leading to an aziridine intermediate

  Simmons–Smith试剂与1-芳基-2-苯基-4-甲硫基-4-仲氨基1,3-二氮杂丁-1,3-二烯1的反应经历了异常的1,4-亚甲基转移，导致形成1-芳基-2-苯基-4-仲氨基咪唑4。然而，其与1-芳基-2-苯基-4-仲氨基-1,3-二氮杂丁-1,3-二烯8的反应进行了初始的1,2-亚甲基转移，导致氮丙啶中间体重新排列为1-芳基-4-苯基咪唑11。
• 1,4-Addition of reformatsky reagent to 1,3-diaza-1,3-butadienes
  作者：Sujit N. Mazumdar、Mohinder P. Mahejan

  DOI：10.1016/s0040-4039(00)97585-3

  日期：1990.1

  The 1,4-conjugated addition of the Reformatsky reagent from ethyl bromoacetate to 1-aryl-4-methylthio-4-sec.amino-2-phenyl-1, 3-dieza-1,3-butadienes gives 1-aryl-2-phenyl-4-sec.amino-1,6-dihydropyrimidin-6-ones.

  将Reformatsky试剂从溴乙酸乙酯中加入1,4-共轭物到1-芳基-4-甲硫基-4-仲氨基-2-苯基-1，3-二氮杂-1,3-丁二烯中，得到1-芳基-2 -苯基-4-仲氨基-1,6-二氢嘧啶-6-。