4-(4-氯苯基)恶唑 | 832099-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(4-氯苯基)恶唑
• 英文名称: 4-(4-Chlorophenyl)oxazole
• 英文别名: 4-(4-chlorophenyl)-1,3-oxazole
• CAS: 832099-59-9
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: BVKCIMXCVGFZEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-甲硫基噻唑 、 4-(4-氯苯基)恶唑 在 三(三苯基膦)羰基氢化铑 、 1,3-双(二环己基磷)丙烷 作用下， 以 邻二氯苯 为溶剂， 反应 3.0h， 以52%的产率得到4-(4-chlorophenyl)-2-(methylthio)oxazole
  参考文献：
  名称：

  Rhodium-Catalyzed 2-Methylthiolation Reaction of Thiazoles/Oxazoles Using 2-(Methylthio)thiazole

  摘要：

  RhH(PPh3)(4) and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium, and various 2-methylthiolated thiazoles and oxazoles were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.

  DOI：

  10.3987/com-14-s(k)59
• 作为产物：
  描述：

  甲酸铵 、 2'-溴-4-氯苯乙酮 在 甲酸 作用下， 生成 4-(4-氯苯基)恶唑
  参考文献：
  名称：

  Discovering novel chemical inhibitors of human cyclophilin A: Virtual screening, synthesis, and bioassay

  摘要：

  Cyclophilin A (CypA) is a member of cyclophilins, a family of the highly homologous peptidyl prolyl cis-trans isomerases (PPIases), which can bind to cyclosporin A (CsA). CypA plays critical roles in various biological processes, including protein folding, assembly, transportation, regulation of neuron growth, and HIV replication. The discovery of CypA inhibitor is now of a great special interest in the treatment of immunological disorders. In this study, a series of novel small molecular CypA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. The SPECS-1 database containing 85,000 small molecular compounds was searched by virtual screening against the crystal structure of human CypA. After SPR-based binding affinity assay, 15 compounds were found to show binding affinities to CypA at submicro-molar or micromolar level (compounds 1-15). Seven compounds were selected as the starting point for the further structure modification in considering binding activity, synthesis difficulty, and structure similarity. We thus synthesized 40 new small molecular compounds (1-6, 15, 16a-q, 17a-d, and 18a-I), and four of which (compounds 16b, 16h 16k,. and 18g) showed high CypA PPIase inhibition activities with IC50S of 2.5-6,2 mu M. Pharmacological assay indicated that these four Compounds demonstrated somewhat inhibition activities against the proliferation of spleen cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.006

文献信息

• Photoinduced [4 + 4], [4 + 2], and [2 + 2] Cycloadditions of <i>o</i>-Quinones with Oxazoles: Chemo-, Regio-, and Diastereoselectivity
  作者：Lei Wang、Yu-Cheng Huang、Yang Liu、Hoong-Kun Fun、Yan Zhang、Jian-Hua Xu

  DOI：10.1021/jo101764f

  日期：2010.11.19

  C4 atom results in steric hindrance for ring closure of the 1,4-diradicals in the [2 + 2] cycloaddition pathway, therefore favoring the [4 + 4] and [4 + 2] cycloaddition pathways. Regio- and diastereoselectivity in the [2 + 2] and [4 + 4] cycloadditions have been discussed based on the thermodynamic stability of the relevant triplet diradical intermediates and the conformations of these diradicals suitable

  研究了1,2-二羰基化合物菲醌（PQ），1-乙酰基Isatin（IS）和苯甲腈（BZ）与恶唑1a - j的光诱导反应。在PQ与恶唑的光反应中，除了源自[4 + 2]环加成的1,4-二恶英和来自Paternó-Büchi[2 + 2]反应的氧杂环丁烷外，还形成了[4 + 4]环加成产物。与1a，1c，1g，1i和1j的反应，与醌的二羰基单元（O═C-C═O）和恶唑的C═N-C═C部分作为两个4π加成。IS与恶唑1f和1g的光反应在IS与1a，1c，1e，1h和1i进行光反应时，仅给出[4 + 4]环加成产物，[4 + 4]个乘积与[2 + 2]个乘积一起形成。这些光环加成中的反应途径分配在很大程度上取决于恶唑环上的取代模式。在恶唑的C 2原子处存在取代基会通过在相应的1,7-双自由基中间体中形成自由基对自由基对重组而形成[4 + 4]环加成产物，从而阻碍[4 + 4]途径。C4原子上的取代基会导致[2
• Photoinduced [4 + 4] Cycloadditions of <i>o</i>-Quinones with Oxazoles
  作者：Yan Zhang、Lei Wang、Min Zhang、Hoong-Kun Fun、Jian-Hua Xu

  DOI：10.1021/ol048028t

  日期：2004.12.1

  [Graphics]Photocycloadditions of 9,10-phenanthraquinone (PQ) with oxazoles (1a and 1b) gave [4 + 4] products 2 with the O=C-C=O functionality in PQ and the 2-azadiene moiety in oxazole as 4,pi addends. Photoreactions of 1-acetylisatin (IS) with la, 1c, and ld gave [4 + 4] product A, which underwent further [2 + 2] reactions with another (IS)-I-3* to furnish 5. These regioselective and diastereoselective [4 + 4] photocycloadditions are rationalized by the intervening of the key conformers for ISC and bond formation of the most stable 1,6-diradical intermediates.
• Rhodium-Catalyzed 2-Methylthiolation Reaction of Thiazoles/Oxazoles Using 2-(Methylthio)thiazole
  作者：Mieko Arisawa、Masahiko Yamaguchi、Yuri Nihei

  DOI：10.3987/com-14-s(k)59

  日期：——

  RhH(PPh3)(4) and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium, and various 2-methylthiolated thiazoles and oxazoles were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.
• Discovering novel chemical inhibitors of human cyclophilin A: Virtual screening, synthesis, and bioassay
  作者：Jian Li、Jing Chen、Chunshan Gui、Li Zhang、Yu Qin、Qiang Xu、Jian Zhang、Hong Liu、Xu Shen、Hualiang Jiang

  DOI：10.1016/j.bmc.2005.11.006

  日期：2006.4

  Cyclophilin A (CypA) is a member of cyclophilins, a family of the highly homologous peptidyl prolyl cis-trans isomerases (PPIases), which can bind to cyclosporin A (CsA). CypA plays critical roles in various biological processes, including protein folding, assembly, transportation, regulation of neuron growth, and HIV replication. The discovery of CypA inhibitor is now of a great special interest in the treatment of immunological disorders. In this study, a series of novel small molecular CypA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. The SPECS-1 database containing 85,000 small molecular compounds was searched by virtual screening against the crystal structure of human CypA. After SPR-based binding affinity assay, 15 compounds were found to show binding affinities to CypA at submicro-molar or micromolar level (compounds 1-15). Seven compounds were selected as the starting point for the further structure modification in considering binding activity, synthesis difficulty, and structure similarity. We thus synthesized 40 new small molecular compounds (1-6, 15, 16a-q, 17a-d, and 18a-I), and four of which (compounds 16b, 16h 16k,. and 18g) showed high CypA PPIase inhibition activities with IC50S of 2.5-6,2 mu M. Pharmacological assay indicated that these four Compounds demonstrated somewhat inhibition activities against the proliferation of spleen cells. (c) 2005 Elsevier Ltd. All rights reserved.