N-(4-nitrophenyl)morpholine-4-carbothioamide | 364339-83-3

• 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-(4-nitrophenyl)morpholine-4-carbothioamide
• 英文别名: N-(4-nitrophenyl)-N’-morpholinothiourea；p-C6H4(NO2)NHC(S)N(CH2CH2)2O
• CAS: 364339-83-3
• 化学式: C₁₁H₁₃N₃O₃S
• mdl: MFCD01438445
• 分子量: 267.309
• InChiKey: NXRGFTFOOPUGKK-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)morpholine-4-carbothioamide 在 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以0.0766 g的产率得到N-(dimorpholinomethylene)-4-nitroaniline
  参考文献：
  名称：

  pH值3 P / I 2的介导的合成N，N- ' ，N “ -取代的胍和2- Iminoimidazolin -4-酮从芳基异硫氰酸酯

  摘要：

  描述了一种方便的一锅法，用于合成由Ph 3 P / I 2系统介导的无环和环状胍。芳基异硫氰酸酯与胺的顺序缩合，然后进行脱氢硫化和鸟苷化，可能同时导致对称和不对称的N，N ' ，N '' -取代的衍生物。通过串联的胍基化-环化反应，还可以从芳基异硫氰酸酯与氨基酸甲酯的反应中以高收率制备一系列2-iminoimidazolin-4-ones。

  DOI：

  10.1021/acs.joc.7b01794
• 作为产物：
  描述：

  吗啉 、 异硫代氰基4-硝基苯酯 以 乙醚 为溶剂， 生成 N-(4-nitrophenyl)morpholine-4-carbothioamide
  参考文献：
  名称：

  二取代和三取代的硫脲单阴离子和二阴离子镍（II）配合物

  摘要：

  摘要乙酸镍（II），1,2-双（二苯基膦基）乙烷（dppe）和二或三取代的硫脲R1NHC（S）R2R3（R3 = H或烷基）与三甲胺在热甲醇中的反应生成阳离子含有N，S螯合的硫脲单阴离子配体[Ni {SC（NR2R3）NR1}（dppe）] +的镍（II）配合物，可以很容易地将其BPh4-盐分离出来。报道了[Ni {SC（NMe2）NPh}（dppe）] + BPh4-的X射线晶体结构。

  DOI：

  10.1016/j.ica.2010.12.011

文献信息

• A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents
  作者：Vjekoslav Štrukil、Marina D. Igrc、László Fábián、Mirjana Eckert-Maksić、Scott L. Childs、David G. Reid、Melinda J. Duer、Ivan Halasz、Cristina Mottillo、Tomislav Friščić

  DOI：10.1039/c2gc35799b

  日期：——

  The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic–aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.

  异硫氰酸酯与胺的机械化学点击偶联反应已被用作模型反应，证明了无溶剂研究实验室的概念适用于小有机分子的合成，该概念消除了化学合成或结构表征中对大量溶剂的使用。虽然通过简单手动研磨反应物可以实现高产率的点击偶联，但使用电动、数字可控的实验室研磨机提供了一种快速、定量且普遍适用的方法，用于合成对称和非对称的芳香或芳香-脂肪族硫脲。与手工研钵合成相比，电动球磨技术（干磨或液体辅助研磨）在合成49种不同的硫脲衍生物中展示了其效率的提升。通过将机械化学产品的粉末X射线衍射数据与剑桥结构数据库（CSD）中的结构信息或通过单晶X射线衍射获得的信息进行比较，表明机械化学合成的硫脲衍生物在化学意义上是纯净的，同时在超分子意义上也可以是纯净的，即在所有结构探索的情况下，产品只包含一种多晶型物。作为我们之前关于无溶剂合成配位聚合物工作的延伸，现在证明了选定的硫脲衍生物的多晶型和化学纯度（后者通过定量反应产率得到证实）能够通过粉末X射线衍射辅助的固态核磁共振光谱直接进行无溶剂的结构表征。
• A Mild Synthesis of 2-Substituted Benzothiazoles via Nickel-Catalyzed Intramolecular Oxidative C–H Functionalization
  作者：Ming-Yuan Gao、Jing-Hang Li、Shi-Bo Zhang、Li-Jun Chen、Yue-Sheng Li、Zhi-Bing Dong

  DOI：10.1021/acs.joc.9b02543

  日期：2020.1.17

  A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C-H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short

  已经报道了从芳基硫脲开始制备2-氨基苯并噻唑的高效合成方法。通过使用镍催化剂，芳基硫脲进行分子内氧化CH键官能化，以良好至优异的产率得到所需的2-氨基苯并噻唑。该方案具有廉价的催化剂，催化剂用量低，反应条件温和，反应时间短，收率良好至优异的特点，并且可以轻松按比例放大至克级，而收率几乎没有下降。
• Nickel(II) complexes of di- and tri-substituted thiourea mono- and di-anions
  作者：Ho Ying Yuen、William Henderson、Allen G. Oliver

  DOI：10.1016/j.ica.2010.12.011

  日期：2011.3

  Abstract Reaction of nickel(II) acetate, 1,2-bis(diphenylphosphino)ethane (dppe), and a di- or tri-substituted thiourea R1NHC(S)R2R3 (R3 = H or alkyl) with trimethylamine in hot methanol gave cationic nickel(II) complexes containing N,S-chelated thiourea monoanion ligands [NiSC(NR2R3)NR1}(dppe)]+, which can be readily isolated as their BPh4− salts. The X-ray crystal structure of [NiSC(NMe2)NPh}(dppe)]+BPh4−

  摘要乙酸镍（II），1,2-双（二苯基膦基）乙烷（dppe）和二或三取代的硫脲R1NHC（S）R2R3（R3 = H或烷基）与三甲胺在热甲醇中的反应生成阳离子含有N，S螯合的硫脲单阴离子配体[Ni SC（NR2R3）NR1}（dppe）] +的镍（II）配合物，可以很容易地将其BPh4-盐分离出来。报道了[Ni SC（NMe2）NPh}（dppe）] + BPh4-的X射线晶体结构。
• Thiazolidinones, their production and use as pharmaceutical agents
  申请人：Siemeister Gerhard

  公开号：US20070037862A1

  公开（公告）日：2007-02-15

  Thiazolidinones of general formula I in which Q, A, B, X, R 1 and R 2 have the meanings that are indicated in the description, as well as those of general formula IA in which Q, A, B, X, R 1 and R 2a have the meanings that are indicated in the description, their production and use as inhibitors of the polo-like kinase (PLK) for treating various diseases as well as intermediate products for the production of thiazolidinones are described.

  通用公式I中的噻唑烷酮，其中Q、A、B、X、R1和R2具有描述中指示的含义，以及通用公式IA中的噻唑烷酮，其中Q、A、B、X、R1和R2ahave具有描述中指示的含义，描述了它们作为极化样激酶（PLK）抑制剂用于治疗各种疾病以及用于噻唑烷酮的生产和使用的中间体产品。
• One-Pot Synthesis of C 2 Symmetric and Asymmetric N,N′,N′′-Substituted Guanidines from Aryl Isothiocyanates and Amines
  作者：Wong Phakhodee、Sirilak Wangngae、Mookda Pattarawarapan

  DOI：10.1055/s-0035-1561201

  日期：——

  Highly substituted guanidines were conveniently prepared through a one-pot reaction between aryl isothiocyanates and amines mediated by the Ph3P–I2/Et3N system. The C 2-symmetric N,N′,N′′-substituted guanidines were readily accessed using a 1:2 molar ratio of an aryl isothiocyanate and an amine; while sequential addition of two different amines in equimolar ratios gave rise to asymmetric derivatives

  高度取代的胍可以通过异硫氰酸芳基酯和胺之间的一锅反应方便地制备，该反应由 Ph3P-I2/Et3N 系统介导。使用 1:2 摩尔比的异硫氰酸芳基酯和胺，可以很容易地获得 C 2 对称 N,N',N''-取代的胍；而以等摩尔比顺序加入两种不同的胺会产生不对称衍生物。伯胺和仲胺都被发现优先与缺电子的异硫氰酸芳基酯反应，在温和的条件下以良好的收率迅速提供胍。