N-2-(pyridyl)-N'-2-methoxyphenylthiourea | 21487-28-5

• 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-2-(pyridyl)-N'-2-methoxyphenylthiourea
• 英文别名: 1-(2-methoxy-phenyl)-3-pyridin-2-yl-thiourea；N-(o-Methoxyphenyl)-N'-(2-pyridyl)thioharnstoff；N-(2-Anisyl)-N'-(2'-pyridyl)-thiocarbamid；Tab. 2, 8a；1-(2-Methoxyphenyl)-3-pyridin-2-ylthiourea
• CAS: 21487-28-5
• 化学式: C₁₃H₁₃N₃OS
• mdl: MFCD00125559
• 分子量: 259.332
• InChiKey: BHHLCPFNFSARSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-2-(pyridyl)-N'-2-methoxyphenylthiourea 在 碘苯二乙酸 作用下， 以 neat (no solvent) 为溶剂， 以79%的产率得到4-methoxy-N-(pyridin-2-yl)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  高价碘（III）介导的3,4-二取代的5-Imino-1,2,4-噻二唑和2-氨基苯并[d]噻唑的无溶剂区域选择性合成

  摘要：

  使用苯基乙酸二乙酸酯（PIDA）已开发出一种方便的合成3,4-二取代的5-亚氨基-1,2,4-噻二唑和2-氨基苯并[ d ]噻唑的方法。该方法涉及在纯净条件下形成无金属的氧化性C-N，N-S和C-S键。高区域选择性，无溶剂条件，较短的反应时间和广泛的官能团相容性是本报告的显着特征。

  DOI：

  10.1002/adsc.201800353
• 作为产物：
  描述：

  2-氨基吡啶 以65%的产率得到
  参考文献：
  名称：

  GUPTA R. C.; NATH R.; SHANKER K.; BHARGAVA K. P.; KISHOR K., J. INDIAN CHEM. SOC., 1978, 55, NO 8, 832-834

  摘要：

  DOI：

文献信息

• Hypervalent Iodine Promoted Regioselective Oxidative C-H Functionalization: Synthesis of<i>N</i>-(Pyridin-2-yl)benzo[<i>d</i>]thi­azol-2-amines
  作者：Arumugam Mariappan、Kandasamy Rajaguru、Somi Santharam Roja、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1002/ejoc.201501202

  日期：2016.1

  Biologically potent N-(pyridin-2-yl)benzo[d]thiazol-2-amines were conveniently synthesized from simple heteroaryl-thioureas through an oxidative C–S bond formation strategy that employed phenyliodine(III) bis(trifluoroacetate) as the oxidant. This protocol features a metal-free approach, a broad scope of substrates, short reaction times, and a simple product purification procedure.

  通过使用苯基碘（III）双（三氟乙酸盐）作为氧化剂的氧化 C-S 键形成策略，从简单的杂芳基硫脲方便地合成了具有生物活性的 N-（吡啶-2-基）苯并[d]噻唑-2-胺. 该协议具有无金属方法、广泛的底物、较短的反应时间和简单的产品纯化程序。
• Anticonvulsant activity and succinate dehydrogenase inhibitory property of new substituted thiobarbiturates
  作者：Anjali Dhasmana、J. P. Barthwal、B. R. Pandey、B. Ali、K. P. Bhargava、S. S. Parmar

  DOI：10.1002/jhet.5570180341

  日期：1981.5

  Eight 1-aryl-3-(2-pyridyl)thiobarbiturates were synthesized and evaluated for their anticonvulsant property and their ability to inhibit succinate dehydrogenase activity of rat brain homogenates. These substituted thiobarbiturates (100 mg./kg., i.p.) provided 20–60% protection against pentylenetetrazol-induced convulsions in albino mice. Low toxicity of these compounds was reflected by their high approximate

  合成了八种1-芳基-3-（2-吡啶基）硫代巴比妥酸酯，并评估了它们的抗惊厥性质以及它们抑制大鼠脑匀浆中琥珀酸脱氢酶活性的能力。这些取代的硫代巴比妥酸酯（100 mg./kg。，腹腔注射）在白化病小鼠中提供了20-60％的保护，防止戊四氮诱发的惊厥。这些化合物的低毒性通过其较高的大约LD 50值反映出来，该值在500-1000 mg./kg的范围内。所有取代的硫代巴比妥酸酯（Im M）均可抑制体外琥珀酸脱氢酶的活性，其抑制程度为10％至72％。
• Structural and spectral studies of N-2-(pyridyl)-, N-2-(4-, 5-, and 6-picolyl)- and N-2-(4,6-lutidyl)-N′-2-methoxyphenylthioureas
  作者：Douglas X. West、John K. Swearingen、Ann K. Hermetet、Lily J. Ackerman

  DOI：10.1016/s0022-2860(00)00824-3

  日期：2001.5

  N-2-(pyridyl)-N ' -2-methoxyphenylthiourea PyTu2OMe, monoclinic, C2/c, a=15.727(3), b=11.251(2), c=15.026(4) Angstrom, beta = 104.78(2)degrees, V = 2570.9(2) Angstrom (3) and 2 = 8; N-2-(4-picolyl)-N ' -2-methoxyphenylthiourea, 4PicTu2OMe, orthothombic, Pbca, a = 11.439(9), b = 15.897(6), c = 14.920(6) Angstrom, V = 2713.0(4) Angstrom (3) and Z = 8; N-2-(5-picolyl)-N ' -2-methoxyphenylthiourea, 5PicTu2OMe. triclinic, P-1, a = 7.586(2), b = 8.505(3), c = 11.308(5) Angstrom, alpha = 73.29(3), beta = 89.04(3), gamma = 83.38(3)degrees, V = 694.0(6)Angstrom (3) and Z = 2; N-2-(6-picolyl)-N ' -2-methoxyphenylthiourea 6PicTu2OMe, monoclinic, P2(1)/c, a = 11.372(4), b = 15.808(4), c = 16.141(7) Angstrom, beta = 102.96(3)degrees V = 2827.8(3) Angstrom (3) and Z = 8 and N-2-(4,6-lutidyl)-N ' -2-methoxyphenylthiourea, 3,6LuTu2OMe, monoclinic, P2(1)/n, a = 7.546(4), b = 23.400(5), c = 8.927(5) Angstrom, beta = 109.42(5)degrees V = 1486.7(2) Angstrom (3) and Z = 4. Some of these molecules have a bifurcated intramolecular hydrogen bond between N 'H and the pyridyl nitrogen and the 2-methoxy oxygen, and all have intermolecular hydrogen bonding between NH and a thione sulfur of a second molecule to form centrosymmetric dimers. Solution H-1 NMR studies (CDCl3) show the N 'H resonance considerably downfield for each thiourea and its position, as well as that of NH, is affected by substituents on the pyridyl ring. (C) 2001 Elsevier Science B.V. All rights reserved.
• Syntheses, molecular structures, and self-assemblies of SFe₃, S₂Fe₃, S₃Fe₅, SeFe₃, and Se₂Fe₃ clusters with chelating diaminocarbenes
  作者：Yao-Cheng Shi、Shuai Wang、Sun Xie

  DOI：10.1080/00958972.2015.1079312

  日期：2015.11.2

  The reactions of substituted thioureas and selenoureas with iron carbonyls have been systematically investigated, and five types of SFe3, S2Fe3, S3Fe5, SeFe3, and Se2Fe3 clusters with chelating diaminocarbenes have been synthesized and characterized by X-ray crystallography. The reactions of C3H5NHC(=S)NHAr with Fe-3(CO)(12) afford (mu(3)-S)Fe-3(CO)(7)(mu-CO)(kappa C-3,C,C-C3H5NHCNHAr) (1, Ar = Ph; 2, Ar = 4-H2NC6H4). In contrast, the reactions of (2-C5H4N)NHC(=S)NHN=CHAr with Fe-2(CO)(9) form (mu(3)-S)(2)Fe-3(CO)(7)(kappa N-2,C-(2-C5H4N)NHCNHN=CHAr) (3, Ar = Ph; 4, Ar = 4-CH3C6H4). Likewise, reactions of GNHC(=S)NHC(=O) Ph with Fe-3(CO)(12) provide (mu(3)-S)(2)Fe-3(CO)(7)(kappa N-2,C-GNHCNHC(=O)Ph) (5, G = 2-C5H4N; 6, G = 2-C4H3N2) as well as Fe-3(CO)(8)(mu-CO)(2)(kappa N-2,C-(2-C4H3N2)NHCNHC(=O)Ph). The reaction of (2-C5H4N)NHC(=S) NH2 with Fe-3(CO)(12) gives (mu(3)-S)(2)Fe-3(CO)(7)(kappa N-2,C-(2-C5H4N)NHCNH2) (7). The reactions of GNHC(=S) NHPh with Fe-3(CO)(12) produce (mu(3)-S)(2)Fe-3(CO)(7)(kappa N-2, C-GNHCNHPh) (8, G = 2-C5H4N; 9, G = 2-C4H3N2). Analogously, (2-C5H4N) HC(= S) NH(2- CH3C6H4) offers (mu 3- S) 2Fe(3)(CO) 7(kappa 2N, C( 2- C5H4N) NHCNH(2- CH3C6H4)) (10). However, (2- C5H4N) NHC(= S) NH(2- CH3OC6H4) generates (mu 3- S) 2(mu 4- S) Fe5(CO) 10(mu- CO) 2(kappa 2N, C-(2- C5H4N) NHCNH(2- CH3OC6H4)) (11). Furthermore, the reactions of (2- C5H4N) NHC(= S) NHR with Fe-3(CO) 12 form (mu 3- S) 2(mu 4- S) Fe5(CO) 10(mu- CO) 2(kappa 2N, C( 2- C5H4N) NHCNHR) (12, R = 2- H2NC6H4; 13, R = 4- H2NC6H4; 14, R = 2- C5H4N). Surprisingly, the reaction of (2- C5H4N) NHC(= S) NHC3H5 with Fe-3(CO) 12 leads to (mu 3- S) 2(mu 4- S) Fe5(CO) 10(mu CO) 2(kappa 2N, C-(2- C5H4N) NHCNHC3H5) (15). The reaction of C3H5NHC(= Se) NHPh with Fe-3(CO) 12 affords (mu 3- Se) Fe-3(CO) 7(mu- CO)(kappa 3C, C, C- C3H5NHCNHPh) (16) as well as [(kappa 2N, C- PhNCNHC3H5) Fe2(CO) 6(mu 4- Se) Fe2(CO) 6] 2(mu 4- Se). As with (2- C4H3N2) NHC(= S) NHPh, (2- C4H3N2) NHC(= Se) NHPh offers (mu(3)-Se)(2)Fe-3(CO)(7)(kappa N-2,C-(2-C4H3N2)NHCNHPh) (17). Unlike (2-C5H4N)NHC(=S)NH (2-CH3OC6H4), (2-C5H4N) NHC(=Se) NH(2-CH3OC6H4) yields (mu(3)-Se)(2)Fe-3(CO)(7)(kappa N-2,C-(2-C5H4N) NHCNH(2-CH3OC6H4)) (18). By virtue of N-H...N, N-H...O, and C-H...O intermolecular hydrogen bonds along with other non-covalent interactions, these new organometallic clusters exhibit interesting supramolecular structures
• Gupta; Nath; Shanker, Journal of the Indian Chemical Society, 1978, vol. 55, # 8, p. 832 - 834
  作者：Gupta、Nath、Shanker、et al.

  DOI：——

  日期：——