3-甲基-1,4-二苯基-1H-吡唑-5-胺 | 58314-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-甲基-1,4-二苯基-1H-吡唑-5-胺
• 英文名称: 5-amino-3-methyl-1,4-diphenyl-1H-pyrazole
• 英文别名: 3-methyl-1,4-diphenyl-1H-pyrazol-5-amine；1,4-diphenyl-3-methyl-5-aminopyrazole；5-methyl-2,4-diphenyl-2H-pyrazol-3-ylamine；5-Methyl-2,4-diphenyl-2H-pyrazol-3-ylamin；5-amino-3-methyl-1,4-diphenylpyrazole；5-methyl-2,4-diphenylpyrazol-3-amine
• CAS: 58314-81-1
• 化学式: C₁₆H₁₅N₃
• mdl: MFCD00140635
• 分子量: 249.315
• InChiKey: DMKCZUXCQWLBOI-UHFFFAOYSA-N

物化性质

• 溶解度：
  31.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3-甲基-1,4-二苯基-1H-吡唑-5-胺 在 碘苯二乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以91%的产率得到3-methyl-Z-2-phenyl-E-3-(phenylazo)acrylonitrile
  参考文献：
  名称：

  5-氨基-1,4-二芳基-1H-吡唑的无金属开环：轻松获得 2-芳基-3-芳基偶氮丙烯腈

  摘要：

  在尝试使用高价碘试剂对 5-氨基吡唑进行分子内N-芳基化的同时，合成了各种 2-芳基-3-芳基偶氮丙烯腈。该合成涉及苯基碘二乙酸酯在室温下辅助 5-氨基吡唑的开环。提出了形成偶氮烯烃的合理机制。

  DOI：

  10.1002/jhet.4439
• 作为产物：
  描述：

  苯肼 、 α-苯乙酰乙腈 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 3.0h， 以99%的产率得到3-甲基-1,4-二苯基-1H-吡唑-5-胺
  参考文献：
  名称：

  5-氨基-1,4-二芳基-1H-吡唑的无金属开环：轻松获得 2-芳基-3-芳基偶氮丙烯腈

  摘要：

  在尝试使用高价碘试剂对 5-氨基吡唑进行分子内N-芳基化的同时，合成了各种 2-芳基-3-芳基偶氮丙烯腈。该合成涉及苯基碘二乙酸酯在室温下辅助 5-氨基吡唑的开环。提出了形成偶氮烯烃的合理机制。

  DOI：

  10.1002/jhet.4439

文献信息

• Fused isoquinoline derivatives
  申请人：Gruppo Lepetit S.p.A.

  公开号：US04113731A1

  公开（公告）日：1978-09-12

  Fused isoquinoline derivatives of the general formula ##STR1## wherein: A is a divalent radical selected from the groups ##STR2## wherein R.sub.3 and R.sub.4 each independently represents hydrogen, alkyl,, alkenyl, cycloalkyl, aryl, aralkyl, aralkenyl, cycloalkyl-alkyl or, taken together with the adjacent double bond, represent a cycloalkene containing from 5 to 8 carbon atoms or an aromatic nucleus; R.sub.5 represents hydrogen, hydroxyl, alkyl, alkenyl, cycloalkyl, aryl, aralkyl, aralkenyl or cycloalkyl-alkyl; Y is .dbd.O, .dbd.S or .dbd.NH; X is --O--, --S-- or --NR.sub.6 -- wherein R.sub.6 represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl or cycloalkyl-alkyl; R.sub.1 and R.sub.2 each independently represents hydrogen, alkyl, phenyl, cycloalkyl, alkoxy, alkenyloxy, methylenedioxy, cycloalkoxy, halo or di-alkylamino or, taken together with the adjacent carbon atoms of the benzene ring, form a cycloalkenyl group containing 5 or 6 carbon atoms or an aromatic nucleus fused on the benzene ring. The compounds are essentially prepared through thermal cyclization of a compound of the formula ##STR3## wherein A, X, Y, R.sub.1 and R.sub.2 have the same meanings given before, with the proviso that R.sub.1 and R.sub.2 cannot simultaneously occupy both the ortho positions, B represents hydrogen, R represents an --OR.sub.7 or --NR.sub.8 R.sub.9 radical wherein R.sub.7 is alkyl, aryl or aralkyl and R.sub.8 and R.sub.9 each independently represents hydrogen, alkyl, aryl, aralkyl, or taken together with the adjacent nitrogen atom represent a heterocyclic saturated radical of 5 or 6 atoms which may contain a further hetero-atom selected from oxygen and nitrogen, or the symbols B and R taken together represent a further bond between the adjacent carbon and nitrogen atoms.

  通用公式为##STR1##的融合异喹啉衍生物，其中：A是从组##STR2##中选择的二价基团，其中R.sub.3和R.sub.4分别独立表示氢、烷基、烯基、环烷基、芳基、芳基烷基、芳基烯基、环烷基-烷基，或者与相邻的双键一起表示含有5至8个碳原子的环烷烯或芳香核；R.sub.5表示氢、羟基、烷基、烯基、环烷基、芳基、芳基烷基、芳基烯基或环烷基-烷基；Y是.dbd.O、.dbd.S或.dbd.NH；X是--O--、--S--或--NR.sub.6--，其中R.sub.6表示氢、烷基、环烷基、芳基、芳基烷基或环烷基-烷基；R.sub.1和R.sub.2分别独立表示氢、烷基、苯基、环烷基、烷氧基、烯基氧基、亚甲二氧基、环烷氧基、卤素或二烷基氨基，或者与苯环的相邻碳原子一起形成含有5或6个碳原子的环烷烯基团或融合在苯环上的芳香核。这些化合物基本上是通过化合物的热环化制备的##STR3##其中A、X、Y、R.sub.1和R.sub.2的含义与前述相同，但R.sub.1和R.sub.2不能同时占据邻位，B表示氢，R表示--OR.sub.7或--NR.sub.8 R.sub.9基团，其中R.sub.7是烷基、芳基或芳基烷基，R.sub.8和R.sub.9各自独立表示氢、烷基、芳基、芳基烷基，或者与相邻的氮原子一起表示含有5或6个原子的杂环饱和基团，其可能包含进一步选择的氧和氮杂原子，或者符号B和R一起代表相邻碳原子和氮原子之间的进一步键。
• Rh(<scp>iii</scp>)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides
  作者：Longkun Chen、Mingshuai Zhang、Meichen Liu、Zhuoyuan Liu、Yuetong Qiu、Zhilai Zhang、Fuchao Yu、Jiuzhong Huang

  DOI：10.1039/d3cc05266d

  日期：——

  Highly functionalized benzodiazepine skeletons were efficiently synthesized via a Rh(iii)-catalyzed selective mono- and dual-C–H bond functionalization/cyclization reaction between readily available 1-aryl-5-aminopyrazoles and iodonium ylides under.

  通过 Rh(iii) 催化的选择性单-和双-C-H 键官能化/环化反应，在易得的 1-芳基-5-氨基吡唑和碘鎓酰化物之间高效合成了高官能化苯并二氮杂卓骨架。
• Unexpected dearomatization of N-protected 5-aminopyrazoles at ambient temperature: a simple route to highly functionalized pyrazolines
  作者：Pradeep Natarajan、Arpita Chatterjee、Siddharth Jaya Sajeevan J.、Saravanan Peruncheralathan

  DOI：10.1039/d4ob00879k

  日期：——

  We present a new strategy for the dearomatized hydroxylation of 5-aminopyrazoles using a hypervalent iodine reagent at room temperature. This method produces a series of 4-hydroxy-5-iminopyrazolines with good to excellent yields within 2 hours. Additionally, we demonstrate a domino reaction for the synthesis of 4-hydroxy-pyrazolones. Mechanistic studies indicate that the dearomatization proceeds through

  我们提出了一种在室温下使用高价碘试剂对 5-氨基吡唑进行脱芳构羟基化的新策略。该方法可在 2 小时内以良好至优异的产率生产一系列 4-羟基-5-亚氨基吡唑啉。此外，我们还演示了合成 4-羟基-吡唑啉酮的多米诺骨牌反应。机理研究表明脱芳构化是通过阳离子中间体进行的。
• Pd-catalyzed direct arylation of phenylpyrazole: Synthesis of fipronil derivatives with aryl boronic acids promoted by a stoichiometric amount of NIS
  作者：Ting Lv、Xiao-Hong Zhang、Jiang-Sheng Han、Ping Zhong

  DOI：10.1016/j.jfluchem.2012.02.007

  日期：2012.5

  The palladium-catalyzed direct arylation of phenylpyrazole with aryl boronic acid promoted by a stoichiometric amount of NIS has been reported. Several phenyl pyrazoles, especially for those with trifluoromethyl groups, can participate in the reaction, providing a series of fipronil derivatives of 4-aryl-phenylpyrazole with potential bioactivity in moderate to good yields. All the compounds were characterized by H-1 NMR, C-13 NMR and FIRMS spectroscopic techniques. (c) 2012 Elsevier B.V. All rights reserved.
• Methods and Compositions for the Treatment of RAS Associated Disorders
  申请人：Ratner Nancy

  公开号：US20120302581A1

  公开（公告）日：2012-11-29

  The instant disclosure relates to compositions that may be useful as therapeutic agents for the treatment of disorders associated or caused by Ras deregulation or dysregulation, for example, disorders associated with alterations in the NF1 gene such as neurofibromatosis type I, fungal infections such as those caused by Candida albicans , and proliferative disorders such as glioblastoma.