4-methyl-5-methoxy-2-(4-methoxyphenyl)oxazole | 159881-08-0

• 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-methyl-5-methoxy-2-(4-methoxyphenyl)oxazole
• 英文别名: 4-methyl-5-methoxy-2-(p-methoxyphenyl)oxazole；5-Methoxy-2-(4-methoxyphenyl)-4-methyl-1,3-oxazole
• CAS: 159881-08-0
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: HYXIHXIRFGBKBV-UHFFFAOYSA-N

物化性质

• 沸点：
  342.6±52.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-5-methoxy-2-(4-methoxyphenyl)oxazole 在 氧气 、 亚甲兰 作用下， 生成 Dimethyl 2-[2-hydroperoxy-2-methoxy-2-(4-methoxyphenyl)ethylidene]propanedioate
  参考文献：
  名称：

  Iesce, M. Rosaria; Cermola, Flavio; Graziano, M. Liliana, Journal of the Chemical Society. Perkin transactions I, 1994, # 1, p. 147 - 152

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (4-methoxybenzoyl)-L-alaninate 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255 mg的产率得到4-methyl-5-methoxy-2-(4-methoxyphenyl)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

• Synthesis of 2,5-Dihydro-1,2,4-oxadiazoles through Formal [3 + 2] Cycloaddition of Oxazoles with Nitrosobenzene Derivatives
  作者：Hiroyuki Suga、Xiaolan Shi、Toshikazu Ibata

  DOI：10.1246/bcsj.71.1231

  日期：1998.5

  The reactions of substituted oxazoles with nitrosobenzene gave 2-phenyl-2,5-dihydro-1,2,4-oxadiazoles regioselectively through formal [3 + 2] cycloadditions proceeding via a ringopening of oxazoles by an attack of nitrosobenzene. The reactions with 1-chloro- and 1-methyl-4-nitrosobenzenes also produced the corresponding 2,5-dihydro-1,2,4-oxadiazoles regioselectivity.

  取代的恶唑与亚硝基苯的反应通过正式的 [3 + 2] 环加成反应区域选择性地得到 2-苯基-2,5-二氢-1,2,4-恶二唑，通过亚硝基苯的攻击使恶唑开环进行。与 1-氯-和 1-甲基-4-亚硝基苯的反应也产生了相应的 2,5-二氢-1,2,4-恶二唑区域选择性。
• A chiral cobalt(<scp>ii</scp>) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines
  作者：Baiwei Ma、Weiwei Luo、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c7cc01278k

  日期：——

  A highly efficient catalytic asymmetric Formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N,N'-dioxide/Co(BF4)2.6H2O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained...

  通过手性N，N'-二氧化物/Co(BF4)2.6H2O络合物实现了5-烷氧基恶唑与偶氮二羧酸酯化合物的高效催化不对称形式[3 + 2]环加成反应。获得了一系列多取代的1,2,4-三唑啉化合物。
• Regie-Control of Formal [3 + 2] Cycloadditions of 5-Alkoxyoxazoles with Diethyl Oxomalonate
  作者：Hiroyuki Suga、Xiaolan Shi、Toshikazu Ibata

  DOI：10.1246/cl.1994.1673

  日期：1994.9

  Tin(IV) chloride-catalyzed formal [3 + 2] cycloadditions of 5-alkoxy-2-(p-methoxyphenyl)- or 2-phenyloxazoles with diethyl oxomalonate gave 2-oxazoline-4,5,5-tricarboxylates in high regioselectivity. 4-Substituted 5-alkoxy-2-methyloxazoles showed a trend to shift the regioselectivity to offer more 3-oxazoline-2,5,5-tricarboxylates in terms of regioselectivity than 2-oxazolines.

  氯化锡 (IV) 催化的 5-烷氧基-2-(对甲氧基苯基)-或 2-苯基恶唑与氧代丙二酸二乙酯的缩甲醛 [3 + 2] 环加成反应以高区域选择性得到 2-恶唑啉-4,5,5-三羧酸酯。4-取代的 5-烷氧基-2-甲基恶唑显示出改变区域选择性的趋势，在区域选择性方面提供比 2-恶唑啉更多的 3-恶唑啉-2,5,5-三羧酸盐。
• 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.
• Regioselectivity in Formal [3+2] Cycloaddition Reaction of 5-Alkoxyoxazoles with Diethyl Oxomalonate and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
  作者：Hiroyuki Suga、Xiaolan Shi、Toshikazu Ibata、Akikazu Kakehi

  DOI：10.3987/com-01-9277

  日期：——

  Tin(IV) chloride-catalyzed formal [3 + 2] cycloaddition of 5-alkoxy-2-(p-methoxyphenyl)- or 2-phenyloxazoles with diethyl oxomalonate gave 4,5,5-tris(alkoxycarbonyl)-2-oxazolines in high regioselectivity. Under similar conditions, 4-substituted 5-alkoxy-2-methyloxazoles showed a trend to shift the regioselectivity in favor for 3-oxazolines rather than 2-oxazolines. Reaction of 5-alkoxy-4-ethoxycarbonyloxazoles with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone proceeded only under high pressure to give 2-oxazolines exclusively.