N-propyl-N-phenylthiourea | 4292-70-0

• 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-propyl-N-phenylthiourea
• 英文别名: 1-phenyl-1-propyl-thiourea；N-phenyl-N-propyl-thiourea；N-Phenyl-N-propyl-thioharnstoff；1-Phenyl-1-propyl-2-thioharnstoff；n-Propylphenylthiourea；1-phenyl-1-propylthiourea
• CAS: 4292-70-0
• 化学式: C₁₀H₁₄N₂S
• 分子量: 194.301
• InChiKey: PBMKSSZNWPOGTG-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  299.2±23.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-propyl-N-phenylthiourea 在 溴 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以77.5%的产率得到3-propyl-2-iminobenzothiazoline
  参考文献：
  名称：

  Experimental and Theoretical Studies on the Thermal Decomposition of Heterocyclic Nitrosimines¹

  摘要：

  A series of substituted 2-nitrosiminobenzothiazolines (2) were synthesized by the nitrosation of the corresponding 2-iminobenzothiazolines (6). Thermal decomposition of 2a-f and of the seleno analogue 7 in methanol and of 3-methyl-2-nitrosobenzothiazoline (2a) in acetonitrile, 1,4-dioxane, and cyclohexane followed first-order kinetics. The activation parameters for thermal deazetization of 2a were measured in cyclohexane (DeltaH(double dagger) = 25.3 +/- 0.5 kcal/mol, DeltaS(double dagger) = 1.3 +/- 1.5 eu) and in methanol (DeltaH(double dagger) = 22.5 +/- 0.7 kcal/mol, DeltaS(double dagger) = -12.9 +/- 2.1 eu). These results indicate a unimolecular decomposition and are consistent with a proposed stepwise mechanism involving cyclization of the nitrosimine, followed by loss of N-2. The ground-state conformations of the parent nitrosiminothiazoline (9a) and transition states for rotation around the exocyclic C=N bond, electrocyclic ring closure, and loss of N-2 were calculated using A initio molecular orbital theory at the MP2/6-31G* level. The calculated gas-phase barrier height for the loss of N-2 from 9a (25.2 kcal/mol, MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE) compares favorably with the experimental barrier for 2a of 25.3 kcal/mol in cyclohexane. The potential energy surface is unusual; the rotational transition state 9a-rot-ts connects directly to the orthogonal transition state for ring-closure 9aTS. The decoupling of rotational and pseudopericyclic bond-forming transition states is contrasted with the single pericyclic transition state (15TS) for the electrocyclic ring-opening of oxetene (15) to acrolein (16). For comparison, the calculated homolytic strength of the N-NO bond is 40.0 kcal/mol (MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE).

  DOI：

  10.1021/ja010659k
• 作为产物：
  描述：

  N-丙基苯胺 在 sodium hydroxide 作用下， 生成 N-propyl-N-phenylthiourea
  参考文献：
  名称：

  二硫代缩二脲。第二部分 一些环状导数

  摘要：

  DOI：

  10.1039/jr9550000803

文献信息

• Compounds and compositons for treating C1s-mediated diseases and conditions
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20020037915A1

  公开（公告）日：2002-03-28

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula I 1 or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R 3 , R 4 , X, Y and Z are defined in the specification.

  揭示了一种治疗急性或慢性疾病症状的方法，该疾病是由补体级联的经典途径介导的，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4、X、Y和Z。
• A convenient and efficient method for the synthesis of mono- and N,N-disubstituted thioureas
  作者：Mitsuo Kodomari、Masato Suzuki、Keiko Tanigawa、Tadashi Aoyama

  DOI：10.1016/j.tetlet.2005.06.135

  日期：2005.8

  A convenient method for the synthesis of mono- and N,N-disubstituted thioureas by the debenzoylation of N-substituted- and N,N-disubstituted-N′-benzoylthioureas with hydrazine hydrate under solvent-free conditions has been developed. N-Substituted-N′-benzoylthioureas and hydrazine hydrate were mixed, and stirred at room temperature without a solvent to give the corresponding N-substituted thioureas

  开发了一种方便的方法，该方法在无溶剂条件下通过水合肼将N-取代的和N，N-二取代的-N'-苯甲酰基硫脲进行苯甲酰化来合成单和N，N-二取代的硫脲。混合N-取代的-N'-苯甲酰基硫脲和水合肼，并在室温下在无溶剂的情况下搅拌，以高收率得到相应的N-取代的硫脲。
• Heteroaryl amidines, methylamidines and guanidines and use thereof as protease inhibitors
  申请人：——

  公开号：US20010031781A1

  公开（公告）日：2001-10-18

  The present invention is directed to compounds of Formula I: wherein X is O, S or NR 7 and R 1 -R 7 , Y and Z are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof. Also described are methods for preparing the compounds of Formula I. The novel compounds of the present invention are potent inhibitors of proteases, especially trypsin-like serine proteases, such as chymotrypsin, trypsin, plasmin and urokinase. Certain of the compounds exhibit direct, selective inhibition of urokinase, or are intermediates useful for forming compounds having such activity.

  本发明涉及式 I 的化合物： 其中 X 是 O、S 或 NR 7 和 R 1 -R 7 、Y 和 Z，以及它们的水合物、溶剂或药学上可接受的盐，均已在说明书中阐明。还描述了制备式 I 化合物的方法。本发明的新型化合物是蛋白酶的强效抑制剂，特别是胰蛋白酶样丝氨酸蛋白酶，如糜蛋白酶、胰蛋白酶、凝血酶和尿激酶。其中某些化合物对尿激酶有直接的选择性抑制作用，或者是用于形成具有这种活性的化合物的中间体。
• Hypotensive activity of 3-alkyl-2-iminobenzothiazolines
  作者：Stephen W. Horgan、James K. Woodward、Alfred Richardson、Albert A. Carr

  DOI：10.1021/jm00237a023

  日期：1975.3
• de Beer et al., Journal of Pharmacology and Experimental Therapeutics, 1936, vol. 57, p. 19,22
  作者：de Beer et al.

  DOI：——

  日期：——