5-(4-甲苯基)-1,2,4-恶二唑-3-胺 | 23275-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(4-甲苯基)-1,2,4-恶二唑-3-胺
• 英文名称: 5-(4-tolyl)-1,2,4-oxadiazol-3-amine
• 英文别名: 3-Amino-5-p-tolyl-1.2.4-oxadiazol；5-p-tolyl-[1,2,4]oxadiazol-3-ylamine；5-(4-Methylphenyl)-1,2,4-oxadiazol-3-amine
• CAS: 23275-54-9
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: QFGSQAOPDOZWNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-甲苯基)-1,2,4-恶二唑-3-胺 以 甲醇 为溶剂， 反应 8.0h， 以10%的产率得到5-(4-甲基苯基)-1,3,4-噁二唑-2-胺
  参考文献：
  名称：

  Buscemi, Silvestre; Cicero, Maria G.; Vivona, Nicolo, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1313 - 1316

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-diethyl-4-methylbenzimidamide 在 盐酸羟胺 、 silver nitrate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5-(4-甲苯基)-1,2,4-恶二唑-3-胺
  参考文献：
  名称：

  A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

  摘要：

  An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exotrig cyclization.

  DOI：

  10.1055/s-0032-1317504

文献信息

• Stereospecific Synthesis of (<i>E</i>)-5-Tetrasubstituted-ylidene-3,5-dihydro-4<i>H</i>-imidazol-4-ones
  作者：Rajendraprasad Kotagiri、Zhuoji Deng、Wei Xu、Qian Cai

  DOI：10.1021/acs.orglett.9b01063

  日期：2019.6.7

  A stereospecific synthesis of (E)-5-tetrasubstituted-ylidene-3,5-dihydro-4H-imidazol-4-one derivatives is demonstrated through a cascade process by combination of a Michael addition and Boulton–Katritzky rearrangement. The method provides a simple and efficient approach for the synthesis of (E)-5-tetrasubstituted-ylidene-3,5-dihydro-4H-imidazol-4-ones from the reactions of N-(isoxazol-3-yl)-propiolamides

  （E）-5-四取代亚烷基-3,5-二氢-4 H-咪唑-4-酮衍生物的立体有择合成通过级联过程通过结合迈克尔加成反应和布尔顿-卡特里茨基重排得到证明。该方法提供了一种简单有效的方法，用于从N-（异恶唑-3-基）-的反应中合成（E）-5-四取代-亚烷基-3,5-二氢-4 H-咪唑-4-酮。丙酰胺或带有N或C亲核试剂的N-（1,2,4-恶二唑-3-基）丙酰胺。
• Studies on azole-to-azole interconversions. Substituent effects on the ring-degenerate equilibration between 3-aroylamino-5-methyl-1,2,4-oxadiazoles and 3-acetylamino-5-aryl-1,2,4-oxadiazoles
  作者：Silvestre Buscemi、Vincenzo Frenna、Nicolò Vivona、Giovanni Petrillo、Domenico Spinelli

  DOI：10.1016/0040-4020(95)98709-q

  日期：1995.4

  involved. In the first case the effect of X is meagre and 3-acetylamino-5-aryl-1,2,4-oxadiazoles are more stable than the 3-aroylamino-5-methyl isomers. Vice-versa, when anions are involved the substituent effect is remarcable and the equilibrium can be, for strongly electron-withdrawing X-groups, even largely shifted towards the anions of the 3-aroylamino-5-methyl-1,2,4-oxadiazoles.

  通过1 H NMR测量，已经在CD 3 OD和t BuOK / CD 3 OD中研究了标题反应。已经发现，无论涉及中性或阴离子形式，平衡组成和芳基部分中X-取代基对其施加的作用都完全不同。在第一种情况下，X的作用微不足道，3-乙酰氨基-5-芳基-1,2,4-恶二唑比3-芳酰基氨基-5-甲基异构体更稳定。反之亦然，当涉及阴离子时，取代基的作用是可区分的，并且对于强烈吸电子的X-基团，其平衡甚至可能朝着3-aroylamino-5-methyl-1,2,4-的阴离子转移。恶二唑。
• Base-Promoted Tandem S_NAr/Boulton–Katritzky Rearrangement: Access to [1,2,4]Triazolo[1,5-<i>a</i>]pyridines
  作者：Zihao Li、Kongxi Qiu、Xiao Yang、Wei Zhou、Qian Cai

  DOI：10.1021/acs.orglett.2c00863

  日期：2022.4.29

  A base-promoted tandem SNAr/Boulton–Katritzky rearrangement is developed. It offers a simple and straightforward method for the formation of functionalized [1,2,4]triazolo[1,5-a]pyridines from 1,2,4-oxadiazol-3-amines or 3-aminoisoxazoles with 2-fluoropyridines.

  开发了一种碱基促进的串联 S N Ar/Boulton-Katritzky 重排。它提供了一种从 1,2,4-恶二唑-3-胺或 3-氨基异恶唑与 2-氟吡啶形成官能化 [1,2,4]三唑并[1,5- a ]吡啶的简单直接的方法。
• 6, 11-BRIDGED BIARYL MACROLIDES
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：EP2203435B1

  公开（公告）日：2018-07-18
• 6,11-BRIDGED BIARYL MACROLIDES
  申请人：KIM IN JONG

  公开号：US20090118506A1

  公开（公告）日：2009-05-07

  The present invention discloses compounds of formula I, II or, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.