5H-5-methyl-2-(2-methylphenyl)oxazol-4-one | 1286783-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5H-5-methyl-2-(2-methylphenyl)oxazol-4-one
• 英文别名: 5-Methyl-2-(2-methylphenyl)-1,3-oxazol-4-one；5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-one
• CAS: 1286783-49-0
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: LWKBXYJGKWKITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dec-1-yn-3-one 、 5H-5-methyl-2-(2-methylphenyl)oxazol-4-one 在 (S)-bis[3,5-bis(trifluoromethyl)phenyl][1,5,7-triazabicyclo-[4.3.0]-non-5-ene-3-spiro-6'-(6',7'-dihydro-5'H-dibenzo[a,c]cycloheptene)-8-yl]methanol 作用下， 以 甲苯 为溶剂， 反应 38.0h， 以90%的产率得到
  参考文献：
  名称：

  Chiral Guanidine-catalyzed 1,4-Addition Reaction of 5H-Oxazol-4-ones to Alkynones

  摘要：

  使用在适当位置带有羟基的手性胍催化剂，开发了 5H-恶唑-4-酮与炔酮的不对称 1,4-加成反应，并将其应用于多种底物。该方法提供了合成上有用的具有手性季α-碳原子的烯酮取代的α-羟基酸衍生物。

  DOI：

  10.1246/cl.2012.1675

文献信息

• Highly enantioselective allylic alkylation of 5 H -oxazol-4-ones with Morita-Baylis-Hillman carbonates
  作者：Han Xu、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tet.2018.06.055

  日期：2018.8

  An organocatalytic enantioselective allylic alkylation of 5H-oxazol-4-ones with Morita-Baylis-Hillman carbonates has been developed. With 10 mol% of commercially available cinchonidine, a wide range of substituted 5H-oxazol-4-one derivatives were constructed in good-to-excellent yields with high diastereo- and enantioselectivities. The allylic alkylation adducts obtained are valuable precursors for

  已经开发了用Morita-Baylis-Hillman碳酸盐对5 H-恶唑-4-酮进行有机催化对映选择性烯丙基烷基化反应。用10 mol％的市售可可宁定，以良好至优异的产率以及高的非对映选择性和对映选择性，构建了范围广泛的取代的5 H-恶唑-4-酮衍生物。获得的烯丙基烷基化加合物是用于合成手性α-烷基α-羟基羧酸衍生物的有价值的前体，其代表许多生物活性化合物中的一系列通用结构单元。
• Organocatalytic Asymmetric Michael Addition of 5<i>H</i>-Oxazol-4-ones to Nitroolefins
  作者：Baokun Qiao、Yongqiang An、Qian Liu、Wenguo Yang、Hongjun Liu、Juan Shen、Lin Yan、Zhiyong Jiang

  DOI：10.1021/ol401062z

  日期：2013.5.17

  The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral alpha-alkyl-alpha-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.
• Highly enantioselective α-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides
  作者：Mei Xu、Baokun Qiao、Shaobo Duan、Hongjun Liu、Zhiyong Jiang

  DOI：10.1016/j.tet.2014.09.037

  日期：2014.11

  An unprecedented asymmetric alpha-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides has been established, to access various alpha-sulfenylated adducts with good to excellent enantioselectivities (86-95% ee) by utilizing a cinchona alkaloid-derived squaramide as catalyst. The conditions of this alpha-sulfenylation protocol simultaneously satisfy N-(arylthio)succinimides, N-(benzylthio)succinimides, and N-(alkylthio)succinimides by tuning the substituted groups of 5H-oxazol-4-ones on the 2-position as well as additives. (C) 2014 Elsevier Ltd. All rights reserved.
• Highly<i>Z</i>-Selective Asymmetric 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
  作者：Tomonori Misaki、Kei Kawano、Takashi Sugimura

  DOI：10.1021/ja200283n

  日期：2011.4.20

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.
• Chiral Guanidine-catalyzed 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones to Alkynones
  作者：Tomonori Misaki、Nari Jin、Kei Kawano、Takashi Sugimura

  DOI：10.1246/cl.2012.1675

  日期：2012.12.5

  An asymmetric 1,4-addition reaction of 5H-oxazol-4-ones to alkynones using chiral guanidine catalysts bearing a hydroxy group at the appropriate position was developed, and applied to several substrates. The method provides a synthetically useful enone-substituted α-hydroxy acid derivatives with a chiral quaternary α-carbon atom.

  使用在适当位置带有羟基的手性胍催化剂，开发了 5H-恶唑-4-酮与炔酮的不对称 1,4-加成反应，并将其应用于多种底物。该方法提供了合成上有用的具有手性季α-碳原子的烯酮取代的α-羟基酸衍生物。