4-methoxy-2-phenylbenzo[d]oxazole | 30616-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methoxy-2-phenylbenzo[d]oxazole
• 英文别名: 4-methoxy-2-phenylbenzoxazole；4-Methoxy-2-phenylbenzoxazole；4-methoxy-2-phenyl-1,3-benzoxazole
• CAS: 30616-79-6
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: VBYYNIBHMVUTLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-甲氧基苯基)苯甲酰胺 在 4-硝基碘苯 、 Oxone 、 三氟甲磺酸 作用下， 反应 48.0h， 以15%的产率得到4-methoxy-2-phenylbenzo[d]oxazole
  参考文献：
  名称：

  Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C–H Functionalization and C–O/S Bond Formation

  摘要：

  An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.

  DOI：

  10.1021/jo501216h

文献信息

• Metal‐Free Oxidative Condensation of Catechols, Aldehydes and NH ₄ OAc towards Benzoxazoles
  作者：Shaofeng Wu、Dan Zhou、Furong Geng、Jianyu Dong、Lebin Su、Yongbo Zhou、Shuang‐Feng Yin

  DOI：10.1002/adsc.202100249

  日期：——

  facile and green synthesis of such valuable compounds from easily available substrates will make a contribution to drug, material, and fine chemistry. A method for the synthesis of benzoxazoles from catechols, aldehydes and ammonium acetate is developed using NaIO4 as oxidant under metal- and additive-free conditions. A broad range of benzoxazoles including some fluorescent whitening agents, JTP-426467

  苯并恶唑广泛存在于生物活性化合物、天然产物、药物和功能材料中。因此，从容易获得的底物轻松和绿色合成这些有价值的化合物将为药物、材料和精细化学做出贡献。开发了一种在无金属和无添加剂条件下使用 NaIO 4作为氧化剂从儿茶酚、醛和醋酸铵合成苯并恶唑的方法。广泛的苯并恶唑，包括一些荧光增白剂、JTP-426467 和 tafamidis 类似物，以 56-95% 的产率合成，具有出色的官能团耐受性。机械研究表明，一个有趣的o-亚氨基环己二烯醇中间体参与反应。该协议的这些显着特点使其成为苯并恶唑合成的替代方案。
• Base-Free Selective <i>O</i> -Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles
  作者：Wei-Min Shi、Xiao-Hua Li、Cui Liang、Dong-Liang Mo

  DOI：10.1002/adsc.201700906

  日期：2017.12.11

  of functionalized 2‐substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selective O‐arylation and sequential [3,3]‐rearrangement under metal‐free conditions. O‐arylation of amidoximes was promoted by 3 Å molecule sieves in the absence of a base and a sequential TFA‐mediated [3,3]‐rearrangement was used to synthesize 2‐substituted benzoxazoles. Both of

  在无金属条件下，可以通过选择性O芳基化和顺序[3,3]重排，从ox胺肟和二芳基碘鎓盐中以高收率制备各种功能化的2-取代苯并恶唑。ø偕胺肟的-arylation用3埃分子筛在不存在碱的和促进连续TFA介导的，使用[3,3] -rearrangement以合成2-取代的苯并恶唑。两者的ø -芳基产品和重排产物用宽范围敏感的官能团，如酯，醛，硝基，乙烯基，胺和酰胺基团除了卤化物的兼容。分两步以克规模制备了带有双苯并恶唑的双齿N-配体。
• A novel strategy for the construction of substituted benzoxazoles via a tandem oxidative process
  作者：Lijun Gu、Cheng Jin、Junming Guo、Lizhu Zhang、Wei Wang

  DOI：10.1039/c3cc46375c

  日期：——

  A practical and simple synthesis of benzoxazoles from easily available substrates was developed. The protocol is triggered by an iron-catalyzed tandem oxidative process from simple toluene derivatives and 2-aminophenols. This method represents a straightforward approach to access substituted benzoxazoles.

  从容易获得的底物上开发了一种实用，简单的苯并恶唑合成方法。该协议由简单的甲苯衍生物和2-氨基苯酚的铁催化串联氧化过程触发。该方法代表了一种直接的方法来获得取代的苯并恶唑。
• Synthesis of 2-Arylbenzoxazoles through Oxidation of C-H Bonds Adjacent to Oxygen Atoms
  作者：Lijun Gu、Wei Wang、Yong Xiong、Xiangzhong Huang、Ganpeng Li

  DOI：10.1002/ejoc.201301504

  日期：2014.1

  A practical and simple synthesis of benzoxazoles from easily available substrates was developed. The protocol is triggered by an iron-catalyzed tandem oxidative process from simple ether derivatives.

  开发了一种从容易获得的底物合成苯并恶唑的实用且简单的方法。该协议由来自简单醚衍生物的铁催化串联氧化过程触发。
• ALPHA, BETA-UNSATURATED AMIDE COMPOUND
  申请人：Kyowa Kirin Co., Ltd.

  公开号：EP3712129A1

  公开（公告）日：2020-09-23

  An object of the present invention is to provide an α,β-unsaturated amide compound or a pharmaceutically acceptable salt or the like thereof having anticancer activity and the like. The α,β-unsaturated amide compound represented by the following formula (I) or a pharmaceutically acceptable salt or the like thereof has anticancer activity and the like: [wherein, "A" represents optionally substituted heterocyclic diyl, R1 represents hydrogen atom or optionally substituted lower alkyl, R2 represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted aliphatic heterocyclic group or optionally substituted aromatic heterocyclic group, X represents -O-, -S-, -SO2-, -NRX1- (wherein, RX1 represents hydrogen atom or lower alkyl), -CHRX2- (wherein, RX2 represents hydrogen atom or hydroxy), -CH=CH-, -CO- or -NH-CO-, and n1 and n2 are the same or different, and each represents 0 or 1].

  本发明的目的是提供一种具有抗癌活性的α，β-不饱和酰胺化合物或其药学上可接受的盐或类似物。下式（I）代表的α，β-不饱和酰胺化合物或其药学上可接受的盐或类似物具有抗癌活性等： [其中，"A "代表任选取代的杂环二基、 R1 代表氢原子或任选取代的低级烷基、 R2 代表任选取代的芳基、任选取代的环烷基、任选取代的脂肪杂环基团或任选取代的芳香杂环基团、 X代表-O-、-S-、-SO2-、-NRX1-（其中，RX1代表氢原子或低级烷基）、-CHRX2-（其中，RX2代表氢原子或羟基）、-CH=CH-、-CO-或-NH-CO-，以及 n1 和 n2 相同或不同，且各自代表 0 或 1]。