N-(5-chlorobenzo[d]oxazol-2-yl)benzamide | 3083-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-(5-chlorobenzo[d]oxazol-2-yl)benzamide
• 英文别名: N-(5-chloro-benzooxazol-2-yl)-benzamide；2-Benzoylamino-5-chlor-benzoxazol；5-Chloro-2-benzamidobenzoxazole；N-(5-chloro-1,3-benzoxazol-2-yl)benzamide
• CAS: 3083-97-4
• 化学式: C₁₄H₉ClN₂O₂
• 分子量: 272.691
• InChiKey: CLBNTVGSQAWYMI-UHFFFAOYSA-N

物化性质

• 熔点：
  213 °C
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[(3-氯苯基)硫代氨基甲酰]苯甲酰胺 在 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以212 mg的产率得到N-(5-chlorobenzo[d]oxazol-2-yl)benzamide
  参考文献：
  名称：

  二乙酰氧基碘苯通过顺序酰化和脱酰过程辅助C–O键形成：苯并恶唑酰胺的合成及其DFT机理的研究†

  摘要：

  在这项工作中描述了一种使用二乙酰氧基碘苯（DIB）将N-取代的-N'-苯甲酰基硫脲转化为取代的N-苯并恶唑-2-基-酰胺的有效方法。由于DIB的氧化脱氢作用，该转变遵循的是C–O键的形成导致苯并恶唑衍生物的产生，而不是苯并噻唑部分的预期的C–S键的形成。导致苯并恶唑的C–O键形成是由于连续的酰化和脱酰作用以及两摩尔DIB的减少。提出了合理的反应机理，并进行了密度泛函计算以研究反应机理。

  DOI：

  10.1039/c6ob00968a

文献信息

• An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin
  作者：Se-Lin Jung、Seul-Gi Kim、Gee-Hyung Lee、Young-Dae Gong

  DOI：10.5012/bkcs.2012.33.12.4109

  日期：2012.12.20

  An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]-oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo-[d]oxazole resins 4 by cyclization reaction of 2-hydroxy-phenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2-amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane ($CH_2Cl_2$).

  开发了一种高效的固相合成方法，用于合成2-氨基和2-酰胺基苯并[d]噁唑衍生物。该方法的关键步骤是通过2-羟基苯硫脲树脂3的环化反应制备聚合物结合的2-氨基苯并[d]噁唑树脂4。树脂结合的2-羟基苯硫脲3是通过将2-氨基酚加到异硫氰酸酯终端树脂2上制备的，并作为接头树脂的关键中间体。这个核心骨架2-氨基苯并[d]噁唑树脂4通过与各种亲电试剂（如烷基卤化物和酰氯）进行功能化反应，分别生成2-氨基和2-酰胺基苯并[d]噁唑树脂5和6。最后，通过在二氯甲烷中使用三氟乙酸（TFA）切割相应的树脂5和6，可以高产率和纯度地得到2-氨基和2-酰胺基苯并[d]噁唑衍生物7和8。
• Synthesis of Benzoxazole Amides as Novel Antifungal Agents against Malassezia Furfur
  作者：Beom-Joon Kim、Jin-Ah Kim、Young-Kook Kim、Soon-Yong Choi、Hea-Young ParkChoo

  DOI：10.5012/bkcs.2010.31.5.1270

  日期：2010.5.20

  Malassezia is a pathogenic fungus that causes skin diseases, such as tinea versicolor, atopic dermatitis and fatal sepsis. We report the synthesis of a series of benzoxazole amides and evaluation of their antifungal activity against Malassezia furfur. Twelve benzoxazole amides were prepared through the cyclization of the substituted 2-hydroxy aniline with N-(bis-methylsulfanylmethylene) amides. Among the prepared compounds, the compounds 4a, 8b, 8c and 8d showed in vitro antifungal activity.

  马拉色菌是一种致病真菌，可引起皮肤病，如皮肤癣菌、特应性皮炎和致命的败血症。我们报告了一系列苯并恶唑酰胺的合成及其对糠秕马拉色菌抗真菌活性的评估。通过将取代的 2- 羟基苯胺与 N-（双甲硫基亚甲基）酰胺环化，制备了 12 种苯并恶唑酰胺类化合物。在制备的化合物中，化合物 4a、8b、8c 和 8d 具有体外抗真菌活性。
• THIOPHENE-SULFONAMIDE COMPOUNDS
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP1034176A1

  公开（公告）日：2000-09-13
• [EN] THIOPHENE-SULFONAMIDE COMPOUNDS<br/>[FR] COMPOSES THIOPHENE-SULFAMIDES
  申请人：PHARMACIA & UPJOHN S.P.A.

  公开号：WO1999028316A1

  公开（公告）日：1999-06-10

  (EN) Compounds of formula (I) wherein X is O or S; each of R, R1, and R2, which are the same or different, is independently hydrogen, halogen, hydroxy, trifluoromethyl, nitro, amino, phenyl, benzyl, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkanoylamino, formylamino, C1-C6 alkoxy-carbonyl, or an unsaturated pentatomic heteromonocyclic ring containing one to three heteroatoms chosen independently from oxygen, sulphur and nitrogen, wherein the heteromonocyclic ring is unsubstituted or substituted by one or two substituents chosen independently from halogen, hydroxy, trifluoromethyl, nitro, amino, phenyl, benzyl, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkanoylamino, formylamino and C1-C6 alkoxy-carbonyl; R3 is hydrogen, C1-C6 alkyl or a phenyl or benzyl group, in which the phenyl ring or phenyl moiety is unsubstitutedor substituted by one or two substituents chosen independently from halogen, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy, nitro, amino, hydroxy, formylamino, C2-C6 alkanoylamino and C1-C6 alkoxy-carbonyl; each of R4 and R5, which are the same or different, is independently hydrogen or a phenyl ring unsubstituted or substituted by one or two substituents chosen independently from halogen, hydroxy, trifluoromethyl, nitro, amino, phenyl, benzyl, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkanoylamino, formylamino and C1-C6 alkoxy-carbonyl; or R4 and R5 taken together form a C6-C14 aromatic ring system unsubstituted or substituted by one or two substituents chosen independently from halogen, hydroxy, trifluoromethyl, nitro, amino, phenyl, benzyl, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkanoylamino, formylamino and C1-C6 alkoxy-carbonyl; and the pharmaceutically acceptable salts thereof have kynurenine-3-hydroxylase enzyme inhibitory activity.(FR) L'invention se rapporte à des composés représentés par la formule (I) dans laquelle X est O ou S; l'un au moins des groupes que sont R, R1 et R2, qui sont identiques ou différents, est indépendamment hydrogène, halogène, hydroxy, trifluorométhyle, nitro, amino, phényle, benzyle, alkyle C1-C6, alcoxy C1-C6, alcanoylamino C2-C6, formylamino et alcoxy C1-C6-carbonyle ou un noyau hétéromonocyclique pentatomique non saturé comportant un à trois hétéroatomes sélectionnés indépendamment parmi l'oxygène, le soufre et l'azote, ledit noyau hétéromonocyclique étant non substitué ou substitué par un ou deux substituants sélectionnés indépendamment parmi halogène, hydroxy, trifluorométhyle, nitro, amino, phényle, benzyle, alkyle C1-C6, alcoxy C1-C6, alcanoylamino C2-C6, formylamino et alcoxy C1-C6-carbonyle; R3 est hydrogène, alkyle C1-C6, un groupe benzyle ou phényle dans lequel la fraction phényle ou le cycle phényle est non substitué ou substitué par un ou deux substituants sélectionnés indépendamment parmi halogène, trifluorométhyle, alkyle C1-C6, alcoxy C1-C6, nitro, amino, hydroxy, formylamino, alcanoylamino C2-C6 et alcoxy C1-C6-carbonyle; R4 et R5, qui sont identiques ou différents, sont chacun indépendamment hydrogène ou un noyau phényle non substitué ou substitué par un ou deux substituants sélectionnés indépendamment parmi halogène, hydroxy, trifluorométhyle, nitro, amino, phényle, benzyle, alkyle C1-C6, alcoxy C1-C6, alcanoylamino C2-C6, formylamino et alcoxy C1-C6-carbonyle; ou bien R4 et R5 forment conjointement un système cyclique aromatique C6-C14 non substitué ou substitué par un ou deux substituants sélectionnés indépendamment parmi halogène, hydroxy, trifluorométhyle, nitro, amino, phényle, benzyle, alkyle C1-C6, alcoxy C1-C6, alcanoylamino C2-C6, formylamino et alcoxy C1-C6-carbonyle. L'invention se rapporte également à des sels pharmaceutiquement acceptables de ces composés qui présentent une activité inhibitrice dirigée contre l'enzyme kynurénine-3-hydroxylase.
• Diacetoxyiodobenzene assisted C–O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT
  作者：Lokendrajit Nahakpam、Francis A. S. Chipem、Brajakishor S. Chingakham、Warjeet S. Laitonjam

  DOI：10.1039/c6ob00968a

  日期：——

  benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C–S bond formation of the benzothiazole moiety. The C–O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction

  在这项工作中描述了一种使用二乙酰氧基碘苯（DIB）将N-取代的-N'-苯甲酰基硫脲转化为取代的N-苯并恶唑-2-基-酰胺的有效方法。由于DIB的氧化脱氢作用，该转变遵循的是C–O键的形成导致苯并恶唑衍生物的产生，而不是苯并噻唑部分的预期的C–S键的形成。导致苯并恶唑的C–O键形成是由于连续的酰化和脱酰作用以及两摩尔DIB的减少。提出了合理的反应机理，并进行了密度泛函计算以研究反应机理。