N-Benzyl-2-morpholin-4-yl-2-thioxo-acetamide | 219776-56-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Benzyl-2-morpholin-4-yl-2-thioxo-acetamide
• 英文别名: N-benzyl-2-morpholin-4-yl-2-sulfanylideneacetamide
• CAS: 219776-56-4
• 化学式: C₁₃H₁₆N₂O₂S
• 分子量: 264.348
• InChiKey: LEZKCCLIKCHXHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Benzyl-2-morpholin-4-yl-2-thioxo-acetamide 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-Benzyl-5-(bromomethyl)-4,5-dihydro-1,3-thiazole-2-carboxamide hydrobromide
  参考文献：
  名称：

  Synthesis of thiiranylmethylamides from N(S)-allylthiooxamides

  摘要：

  The first representative of N-1-substituted N-2-thiiranylmethylethaneamides has been synthesized from N-1-substituted N-2-allylethaneamides. The formation of thiiranylmethylamides passes through bromine-induced cyclization of N-allylthioamide moiety followed by hydrolysis of 5-bromomethyl-1,3-thiazoline ring.

  DOI：

  10.1080/10426507.2018.1564753
• 作为产物：
  描述：

  benzyl 2,2,2-trichloroacetamide 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,4-双(对甲苯基硫代)-1,3-二硫杂-2,4-二磷杂环丁烷-2,4-二硫化物 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 3.0h， 生成 N-Benzyl-2-morpholin-4-yl-2-thioxo-acetamide
  参考文献：
  名称：

  Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

  摘要：

  The preparation of several N-monosubstituted trichlorothioacetamides by thionation of the corresponding acetamides, with the use of Heimgartner's reagent is described. In contrast to the corresponding amides which umdergo base-induced beta-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02080-2

文献信息

• Novel steroidal 1,3,4-thiadiazines: Synthesis and biological evaluation in androgen receptor-positive prostate cancer 22Rv1 cells
  作者：Anna S. Komendantova、Alexander M. Scherbakov、Alexander V. Komkov、Viktoriya V. Chertkova、Alexey O. Gudovanniy、Elena I. Chernoburova、Danila V. Sorokin、Yaraslau U. Dzichenka、Valerii Z. Shirinian、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1016/j.bioorg.2019.103142

  日期：2019.10

  A flexible approach to previously unknown spirofused and linked 1,3,4-thiadiazine derivatives of steroids with selective control of heterocyclization patterns is disclosed. (N-Arylcarbamoyl)spiroandrostene-17,6′ [1,3,4]thiadiazines and (N-arylcarbamoyl)17-[1′,3′,4′]thiadiazine-substituted androstenes, novel types of heterosteroids, were prepared from 16β,17β-epoxypregnenolone and 21-bromopregna-5,16-dien-20-one

  公开了一种对甾体的以前未知的螺合的和连接的1,3,4-噻二嗪衍生物具有选择性控制杂环化模式的灵活方法。（N-芳基氨基甲酰基）螺雄甾烯17,6'[1,3,4]噻二嗪和（N-芳基氨基甲酰基）17- [1'，3'，4']噻二嗪取代的雄烯酮是由新型杂类固醇制备的16 β，17 β -epoxypregnenolone和21 bromopregna -5,16-二烯-20-酮在良好至高产率通过用草氨酸硫代酰肼的治疗。筛选合成的化合物对人雄激素受体阳性前列腺癌细胞系22Rv1的抗增殖活性。大部分（N-芳基氨基甲酰基）17- [1'，3'，4']噻二嗪取代的雄烯酮显示出 比抗雄激素比卡鲁胺更好的抗增殖能力（IC 50 = 2.1–6.6 µM）。 在研究的系列中，IC 50 = 3.0μM的化合物7d和IC 50  = 2.1μM的化合物7j被证明是活性最高的。铅合成的化合物7j下调22Rv1细胞中AR
• A Straightforward Approach toward Multifunctionalized Pyridazines via Imination/Electrocyclization
  作者：Alexander V. Komkov、Anna S. Komendantova、Leonid G. Menchikov、Elena I. Chernoburova、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1021/acs.orglett.5b01718

  日期：2015.8.7

  A facile synthesis of functionalized 3-carbamide pyridazines starting from readily available chlorovinyl aldehydes and oxamic acid thiohydrazides via cascade imination/electrocyclization is reported. In the presence of p-toluenesulfuric acid, various ketones have been efficiently incorporated into the pyridazine derivatives through a two-step sequence involving a VilsmeierHaack reaction and imination. The synthetic value of this method has been demonstrated by efficient synthesis of steroidal pyridazines.
• Synthesis of carbamoylamidoximes
  作者：V. N. Yarovenko、S. A. Kosarev、I. V. Zavarzin、M. M. Krayushkin

  DOI：10.1007/bf02494503

  日期：1998.10

  A convenient procedure was developed for the synthesis of carbamoylamidoximes by the reaction of N(S)-substituted monothiooxamides with hydroxylamine hydrochloride in pyridine.
• Reactions of monothiooxamides with O-methylhydroxylamine
  作者：I. V. Zavarzin、V. N. Yarovenko、E. I. Chernoburova、M. A. Shchetinina、M. M. Krayushkin

  DOI：10.1023/b:rucb.0000030829.75754.a2

  日期：2004.2

  The reactions of monothiooxamides with O-methylhydroxylamine were studied. Depending on the substituents in monothiooxamides, the reactions result in the formation of hydroxamic C acid derivatives or various N-methoxy derivatives of amidoximes.
• Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides
  作者：Samuel Braverman、Marina Cherkinsky、Ludmila Kedrova

  DOI：10.1016/s0040-4039(98)02080-2

  日期：1998.12

  The preparation of several N-monosubstituted trichlorothioacetamides by thionation of the corresponding acetamides, with the use of Heimgartner's reagent is described. In contrast to the corresponding amides which umdergo base-induced beta-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.