2-(3'-chloropropyl)-5-phenyloxazole | 146941-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3'-chloropropyl)-5-phenyloxazole
• 英文别名: 2-(3-Chloropropyl)-5-phenyl-1,3-oxazole
• CAS: 146941-09-5
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: WQRIJGJOONZBJI-UHFFFAOYSA-N

物化性质

• 沸点：
  344.2±25.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3'-chloropropyl)-5-phenyloxazole 在 苯硅烷 、 cesium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 80.0h， 生成 5-benzoyl-2,3-dihydro-1H-pyrrolizine-6,7-dicarboxylic acid dimethylester
  参考文献：
  名称：

  Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates

  摘要：

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.

  DOI：

  10.1021/jo00058a010
• 作为产物：
  描述：

  2-甲基-5-苯基-噁唑 、 1-溴-2-氯乙烷 在 正丁基锂 作用下， 生成 2-(3'-chloropropyl)-5-phenyloxazole
  参考文献：
  名称：

  Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates

  摘要：

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.

  DOI：

  10.1021/jo00058a010

文献信息

• Rhodium‐Catalyzed Transannulation of <i>N</i> ‐Sulfonyl‐1,2,3‐triazoles with Carboxylic Esters
  作者：Yuya Kaieda、Kosuke Yamamoto、Masami Kuriyama、Osamu Onomura

  DOI：10.1002/adsc.202200544

  日期：2022.9.6

  3-triazoles with carboxylic esters followed by acid-mediated aromatization has been developed, affording a variety of 2,5-disubstituted oxazole derivatives in good to high yields under mild reaction conditions. The present transformation is proposed to involve the intermolecular carbonyl ylide formation between in situ generated α-imino rhodium carbene species and carboxylic esters, which undergoes

  已经开发了一种铑催化的N-磺酰基-1,2,3-三唑与羧酸酯的环化反应，然后是酸介导的芳构化，在温和的反应条件下以良好至高产率提供各种 2,5-二取代恶唑衍生物. 提出本转化涉及原位产生的α-亚氨基铑卡宾物质和羧酸酯之间的分子间羰基内酯形成，其经历相邻α-亚氨基部分的亲核攻击。
• Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates
  作者：Edwin Vedejs、David W. Piotrowski

  DOI：10.1021/jo00058a010

  日期：1993.3

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.