5-methoxy-2-(4-bromophenyl)oxazole | 67567-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxy-2-(4-bromophenyl)oxazole
• 英文别名: 2-(4-bromo-phenyl)-5-methoxy-oxazole；2-(4-Bromophenyl)-5-methoxy-1,3-oxazole
• CAS: 67567-62-8
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: ZRKCSMGBDRDMFI-UHFFFAOYSA-N

物化性质

• 沸点：
  337.6±48.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(4-bromophenyl)oxazole 、 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到
  参考文献：
  名称：

  Titanium(IV)-Catalyzed Stereoselective Synthesis of Spirooxindole-1-pyrrolines

  摘要：

  A stereoselective cyclization between alkylidene oxindoles and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (as low as 5 mol %) to afford spiro[3,3'-oxindole-1-pyrrolines] in excellent yield (up to 99%) and diastereoselectivity (up to 99:1). Using a chiral scandium(III)indapybox/BArF complex affords enantioenriched spirooxindole-1-pyrrolines where a ligand-induced reversal of diastereoselectivity is observed. This methodology is further demonstrated for the synthesis of pyrrolines from malonate alkylidene and coumarin derivatives.

  DOI：

  10.1021/ol5028128
• 作为产物：
  描述：

  N-(4-bromobenzoyl)glycine methyl ester 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以224 mg的产率得到5-methoxy-2-(4-bromophenyl)oxazole
  参考文献：
  名称：

  Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines

  摘要：

  A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.

  DOI：

  10.1021/ol1027305

文献信息

• Komendantov,M.I. et al., Journal of Organic Chemistry USSR (English Translation), 1978, vol. 14, p. 1353 - 1360
  作者：Komendantov,M.I. et al.

  DOI：——

  日期：——
• Titanium(IV)-Catalyzed Stereoselective Synthesis of Spirooxindole-1-pyrrolines
  作者：Joseph J. Badillo、Carlos J. A. Ribeiro、Marilyn M. Olmstead、Annaliese K. Franz

  DOI：10.1021/ol5028128

  日期：2014.12.19

  A stereoselective cyclization between alkylidene oxindoles and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (as low as 5 mol %) to afford spiro[3,3'-oxindole-1-pyrrolines] in excellent yield (up to 99%) and diastereoselectivity (up to 99:1). Using a chiral scandium(III)indapybox/BArF complex affords enantioenriched spirooxindole-1-pyrrolines where a ligand-induced reversal of diastereoselectivity is observed. This methodology is further demonstrated for the synthesis of pyrrolines from malonate alkylidene and coumarin derivatives.
• Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines
  作者：Joseph J. Badillo、Gary E. Arevalo、James C. Fettinger、Annaliese K. Franz

  DOI：10.1021/ol1027305

  日期：2011.2.4

  A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.