1-(3-乙基-1,2-恶唑-5-基)乙酮 | 183373-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-乙基-1,2-恶唑-5-基)乙酮
• 英文名称: 1-(3-ethyl-5-isoxazolyl)-1-ethanone
• 英文别名: 5-acetyl-3-ethylisoxazole；Ethanone, 1-(3-ethyl-5-isoxazolyl)-(9CI)；1-(3-ethyl-1,2-oxazol-5-yl)ethanone
• CAS: 183373-95-7
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: NCDHZRLCHQUZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-乙基-1,2-恶唑-5-基)乙酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以86%的产率得到1-(3-ethyl-5-isoxazolyl)-1-ethanol
  参考文献：
  名称：

  New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

  摘要：

  A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00776-2
• 作为产物：
  描述：

  1-(3-乙基-4,5-二氢-1,2-恶唑-5-基)乙酮 在 γ-manganese dioxide 作用下， 以 苯 为溶剂， 反应 3.0h， 以76%的产率得到1-(3-乙基-1,2-恶唑-5-基)乙酮
  参考文献：
  名称：

  New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

  摘要：

  A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00776-2

文献信息

• Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles
  作者：Arumugam Nagarajan、Gerardo Zepeda、Joaquín Tamariz

  DOI：10.1016/0040-4039(96)01546-8

  日期：1996.9

  Regioselective 1,3-dipolar cycloadditions of captodative 1-acetylvinyl p-nitrobenzoyloxy (1a) with propionitrile oxide, diphenylnitrile imine and diazoalkanes provided the corresponding 5-acetyl- isoxazoles and pyrazoles. Evidence to support the formation of the initial cycloadducts was obtained. The addition of nitrones also proved to be highly regio- and stereoselective.

  封端的1-乙酰乙烯基对硝基苯甲酰氧基（1a）与丙腈氧化物，二苯基腈亚胺和重氮烷烃的区域选择性1,3-偶极环加成反应提供了相应的5-乙酰基-异恶唑和吡唑。获得了支持形成初始环加合物的证据。还证明添加硝酮具有很高的区域选择性和立体选择性。
• Regio- and Stereoselectivity of Captodative Olefins in 1,3-Dipolar Cycloadditions. A DFT/HSAB Theory Rationale for the Observed Regiochemistry of Nitrones
  作者：Rafael Herrera、Arumugam Nagarajan、Miguel A. Morales、Francisco Méndez、Hugo A. Jiménez-Vázquez、L. Gerardo Zepeda、Joaquín Tamariz

  DOI：10.1021/jo001393n

  日期：2001.2.1

  Captodative olefins 1-acetylvinyl carboxylates proved to be highly regioselective dipolarophiles in 1,3-dipolar cycloadditon to propionitrile oxide, arylphenylnitrile imines, diazoalkanes, and nitrones to yield the corresponding 5-substituted heterocycles. The addition of the latter was also stereoselective, being slightly susceptible to steric demand of the carboxylate substituent in the olefin. All atempts

  巯基化烯烃1-乙酰基乙烯基羧酸盐在1,3-偶极环丙二酸，丙腈氧化物，芳基苯基腈亚胺，重氮烷烃和硝酮中具有高区域选择性的双极性亲油性，可生成相应的5-取代的杂环。后者的添加也是立体选择性的，对烯烃中羧酸根取代基的空间需求稍有敏感性。在还原条件下所有试图裂解异恶唑烷NO键的尝试均告失败，从而提供了具有侧基还原作用的多种产物。由于预测了相反的方向，FMO理论未能成功解释用硝酮观察到的区域选择性。最近建立的DFT / HSAB理论模型能够合理化这种区域选择性，
• CRTH2 Receptor Ligands For Medicinal Uses
  申请人：Ulven Trond

  公开号：US20090099189A1

  公开（公告）日：2009-04-16

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis, wherein A represents a carboxyl group —COON, or a carboxyl bioisostere; A 1 , is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Are 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎，其中A代表羧基—COON或羧基生物同位素；A1为氢或甲基；环Ar1是一个可选取代的苯环5-或6-成员的单环杂环，其中AA1CHO—和L2与相邻的环原子连接；环Are2，Ar3各自独立地表示一个苯环或5-或6-成员的单环杂环，或由一个5-或6-成员的碳环或杂环组成的双环系统，该环或环系统被苯并或与一个5-或6-成员的单环杂环融合，该环或环系统是可选取代的；t为0或1；L2和L3是如描述中所定义的连接基团。
• CRTH2 receptor ligands for medicinal uses
  申请人：Ulven Trond

  公开号：US20110269763A1

  公开（公告）日：2011-11-03

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis: wherein A represents a carboxyl group —COOH, or a carboxyl bioisostere; A 1 is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring or 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Ar 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎：其中A代表羧基—COOH或羧基生物同位素；A1为氢或甲基；环Ar1为可选取代的苯环或5-或6-成员的单环杂环，其中AA1CHO—和L2连接到相邻的环原子上；环Ar2、Ar3各自独立地表示苯环或5-或6-成员的单环杂环，或由5-或6-成员的碳环或杂环组成的双环系统，该环或环系统是苯并或与5-或6-成员的单环杂环融合，该环或环系统是可选的取代；t为0或1；L2和L3是如描述中定义的连接基。
• CRTH2 Receptor Ligands for Medical Use
  申请人：7TM Pharma A/S

  公开号：EP2336113A1

  公开（公告）日：2011-06-22

  4-Bromo-2-[1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonyl]phenoxyl acetic acid is useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis.

  4-溴-2-[1-（2,6-二氯苯基）-1H-吡唑-4-甲酰基]苯氧乙酸可用于治疗对调节 CRTH2 受体活性有反应的疾病，如哮喘、鼻炎、过敏性气道综合征和过敏性鼻支气管炎。