5-甲基-2-萘-1-基-1,3-苯并恶唑 | 74839-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-甲基-2-萘-1-基-1,3-苯并恶唑
• 英文名称: 5-methyl-2-(naphthalen-1-yl)benzoxazole
• 英文别名: 5-methyl-2-(naphthalen-1-yl)benzo[d]oxazole；5-Methyl-2-(naphthalen-1-yl)-1,3-benzoxazole；5-methyl-2-naphthalen-1-yl-1,3-benzoxazole
• CAS: 74839-91-1
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: KBTFJNLSJQUKMM-UHFFFAOYSA-N

物化性质

• 沸点：
  412.0±14.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  N,N-二甲基-1-萘胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium t-butanolate 、 三环己基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-甲基-2-萘-1-基-1,3-苯并恶唑
  参考文献：
  名称：

  Palladium-Catalyzed C–H Arylation of (Benzo)oxazoles or (Benzo)thiazoles with Aryltrimethylammonium Triflates

  摘要：

  The C-H arylation of (benzo)oxazoles or (benzo)thiazoles with aryltrimethylammonium triflates was carried out via Pd-catalyzed C-H/C-N cleavage. Oxazoles, thiazoles, benzoxazole, and benzothiazole were arylated using activated and deactivated aryltrimethylamrnonium triflates to give 2-aryl(benzo)oxazoles or 2-aryl(benzo)thiazoles in reasonable to excellent yields.

  DOI：

  10.1021/acs.orglett.5b02458

文献信息

• Synthesis of benzoxazoles <i>via</i> the copper-catalyzed hydroamination of alkynones with 2-aminophenols
  作者：Kohei Oshimoto、Hiroaki Tsuji、Motoi Kawatsura

  DOI：10.1039/c9ob00572b

  日期：——

  describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization

  我们在本文中描述了通过铜与2-氨基苯酚的炔属酮的铜催化加氢胺化来合成苯并恶唑衍生物的方法。该方法以高收率生产了多种官能化的苯并恶唑衍生物。初步的机理实验表明，该反应将通过铜催化的炔烃加氢胺化和β-亚氨基酮的连续分子内环化/铜催化剂促进的苯乙酮的消除而进行。
• Iron(<scp>ii</scp>) bromide-catalyzed oxidative coupling of benzylamines with ortho-substituted anilines: synthesis of 1,3-benzazoles
  作者：Kovuru Gopalaiah、Sankala Naga Chandrudu

  DOI：10.1039/c4ra12490a

  日期：——

  An iron(II) bromide-catalyzed oxidative coupling of benzylamines with 2-amino/hydroxy/mercapto-anilines has been developed, allowing the synthesis of a diversity of substituted 1,3-benzazoles in good to excellent yields. This transformation is compatible with a wide range of functional groups. The method is practical, economical and employs molecular oxygen as an oxidant.

  已经开发出溴化铁（II）催化的苄胺与2-氨基/羟基/巯基苯胺的氧化偶联，从而可以良好的收率合成各种取代的1,3-苯并唑。此转换与各种功能组兼容。该方法实用，经济并且使用分子氧作为氧化剂。
• Palladium-Catalyzed C–H Arylation of (Benzo)oxazoles or (Benzo)thiazoles with Aryltrimethylammonium Triflates
  作者：Feng Zhu、Jian-Long Tao、Zhong-Xia Wang

  DOI：10.1021/acs.orglett.5b02458

  日期：2015.10.2

  The C-H arylation of (benzo)oxazoles or (benzo)thiazoles with aryltrimethylammonium triflates was carried out via Pd-catalyzed C-H/C-N cleavage. Oxazoles, thiazoles, benzoxazole, and benzothiazole were arylated using activated and deactivated aryltrimethylamrnonium triflates to give 2-aryl(benzo)oxazoles or 2-aryl(benzo)thiazoles in reasonable to excellent yields.