5-chloro-2-(2-phenylethyl)-1,3-benzoxazole | 144037-39-8

• 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: 5-chloro-2-(2-phenylethyl)-1,3-benzoxazole
• 英文别名: 5-chloro-2-(phenylethyl)benzo[d]oxazole；5-chloro-2-phenethylbenzo[d]oxazole；Benzoxazole, 5-chloro-2-(2-phenylethyl)-
• CAS: 144037-39-8
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: AVBIFDFYSNAAHE-UHFFFAOYSA-N

物化性质

• 沸点：
  385.6±25.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯-2-氨基苯酚 、 3-苯基丙酸 在 PS-PPh3 、 三氯乙腈 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以93%的产率得到5-chloro-2-(2-phenylethyl)-1,3-benzoxazole
  参考文献：
  名称：

  一种简单有效的一步法，从羧酸合成苯并恶唑和苯并咪唑

  摘要：

  可以在一个简单的步骤中，分别由多种羧酸与2-氨基酚或1,2-苯二胺快速合成苯并恶唑或苯并咪唑。将可商购的PS-PPh 3树脂与微波加热结合使用，可以高收率和高纯度获得各种​​苯并恶唑和苯并咪唑。

  DOI：

  10.1016/j.tetlet.2006.05.052

文献信息

• Transition‐Metal‐Free Alkylation/Arylation of Benzoxazole via Tf ₂ O‐Activated‐Amide
  作者：Zhi‐Jie Niu、Lian‐Hua Li、Xue‐Yuan Liu、Yong‐Min Liang

  DOI：10.1002/adsc.201901078

  日期：2019.11.19

  A transition‐metal‐free approach to the alkylation/arylation of benzoxazole was developed by employing Tf2O‐activated‐amide as the alkylating/arylating reagent. The mild reaction conditions, and particularly insensitivity to air and water, further enhance the synthetic potential in pharmaceutical synthesis.

  通过使用Tf 2 O活化酰胺作为烷基化/芳基化试剂，开发了一种无过渡金属的苯并恶唑烷基化/芳基化方法。温和的反应条件，尤其是对空气和水的不敏感性，进一步提高了药物合成的合成潜力。
• Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents
  作者：C PRAVEEN、A NANDAKUMAR、P DHEENKUMAR、D MURALIDHARAN、P T PERUMAL

  DOI：10.1007/s12039-012-0251-3

  日期：2012.5

  Microwave-assisted synthesis of benzothiazole and benzoxazole libraries via PIFA promoted cyclocondensation of 2-aminothiophenols/2-aminophenols with aldehydes under one-pot condition in good to excellent yields was achieved. Twenty compounds have been investigated for their analgesic activity and showed moderate to good activity.

  通过一锅法条件下，利用PIFA促进的2-氨基硫酚/2-氨基酚与醛的环化缩合反应，实现了苯并噻唑和苯并噁唑库的微波辅助合成，产率良好至优秀。对二十个化合物进行了镇痛活性研究，显示出中等至良好的活性。
• Akbay, Ayseguel; Oeren, Ilkay; Temiz-Arpaci, Oezlem, Arzneimittel-Forschung/Drug Research, 2003, vol. 53, # 4, p. 266 - 271
  作者：Akbay, Ayseguel、Oeren, Ilkay、Temiz-Arpaci, Oezlem、Aki-Sener, Esin、Yalcin, Ismail

  DOI：——

  日期：——
• The synthesis and the structure-activity relationships of some substituted benzoxazoles, oxazolo(4,5-b)pyridines, benzothiazoles and benzimidazoles as antimicrobial agents
  作者：İ Yalçin、İ Ören、E Şener、A Akin、N Uçartürk

  DOI：10.1016/0223-5234(92)90154-s

  日期：1992.6

  The synthesis of a new series of 2,5-disubstituted benzoxazoles 4a-f, 2-substituted oxazolo(4,5-b)pyridines 5a, b, benzothiazoles 6a, b and benzimidazoles 7a, b is described in order to determine their antimicrobial activities and feasible structure-activity relationships (SAR). The synthesized compounds were tested in vitro against 3 Gram-positive, 3 Gram-negative, and a fungus Candida albicans. 4b, 4e and 4f were found to be more active than the others against Klebsiella pneumoniae at a MIC value of 12.5-mu-g/ml. All the derivatives 4-7 exhibited significant antimycotic activity against C albicans. The antibacterial and antimycotic activities of 4-7 are also compared with several standard drugs.
• A simple and efficient one step synthesis of benzoxazoles and benzimidazoles from carboxylic acids
  作者：Ying Wang、Kathy Sarris、Daryl R. Sauer、Stevan W. Djuric

  DOI：10.1016/j.tetlet.2006.05.052

  日期：2006.7

  Benzoxazoles or benzimidazoles can be rapidly and efficiently synthesized from a variety of carboxylic acids with 2-aminophenols or 1,2-phenylenediamines in one simple step, respectively. The use of commercially available PS-PPh3 resin combined with microwave heating delivered a variety of benzoxazoles and benzimidazoles in high yields and purities.

  可以在一个简单的步骤中，分别由多种羧酸与2-氨基酚或1,2-苯二胺快速合成苯并恶唑或苯并咪唑。将可商购的PS-PPh 3树脂与微波加热结合使用，可以高收率和高纯度获得各种​​苯并恶唑和苯并咪唑。