2-methyl-4-phenyl-4H-oxazolin-5-one | 46173-12-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methyl-4-phenyl-4H-oxazolin-5-one
• 英文别名: 2-methyl-4-phenyl-Δ²-oxazolin-5-one；2-methyl-4-phenyloxazol-5(4H)-one；2-Methyl-4-phenyl-5-oxazolon-；2-methyl-4-phenyl-4H-oxazol-5-one；2-Methyl-4-phenyl-5(4H)-oxazolone；2-methyl-4-phenyl-4H-1,3-oxazol-5-one
• CAS: 46173-12-0
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: WSDRTVVFOYBPBO-UHFFFAOYSA-N

物化性质

• 沸点：
  270.9±43.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-phenyl-4H-oxazolin-5-one 生成 2-methyl-4-(2-methyl-5-oxo-4-phenyl-1,3-oxazol-4-yl)-4-phenyl-1,3-oxazol-5-one
  参考文献：
  名称：

  PADWA, A.;AKIBA, MITSUO;COHEN, L. A.;MACDONALD, J. G., J. ORG. CHEM., 1983, 48, N 5, 695-703

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰-DL-苯基甘氨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-4-phenyl-4H-oxazolin-5-one
  参考文献：
  名称：

  Lawesson 试剂促进吖内酯脱氧合成 2,4-二取代噻唑

  摘要：

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。

  DOI：

  10.1039/d2ob01939f

文献信息

• Cyclisation of α-acylamino-acids in the presence of perchloric acid to give 5-oxo-Δ²-oxazolinium perchlorates
  作者：G. V. Boyd、P. H. Wright

  DOI：10.1039/p19720000909

  日期：——

  benzaldehyde to give the hydroperchlorate of the labile geometrical isomer of 4-benzylidene-2-phenyloxazolinone. Ten N-substituted oxo-oxazolinium perchlorates were prepared and their reactions with benzaldehyde and amines are reported. The bicyclic perchlorate, obtained from p-nitrobenzoyl-L-proline, is easily racemised, probably via a mesoionic oxazolium oxide; the corresponding diphenylamino-compound is optically

  乙酸酐和高氯酸的简单α酰氨基酸的产率-5-氧代Δ动作2个-oxazolinium高氯酸盐，其可以被去质子化，以相应的饱和恶唑啉-5-酮。N-苯甲酰基-L-苯基丙氨酸得到L -4-苄基-2-苯基恶唑啉酮的氢高氯酸盐。由马尿酸制得的盐在用水，甲醇和各种胺处理后会发生开环反应。它与苯甲醛缩合，得到4-亚苄基-2-苯基恶唑啉酮的不稳定几何异构体的氢高氯酸盐。制备了十种N-取代的氧代-恶唑啉鎓高氯酸盐，并报道了它们与苯甲醛和胺的反应。从p获得的双环高氯酸盐-硝基苯甲酰基-L-脯氨酸很容易消旋，可能是通过中性离子的恶唑鎓氧化物消旋；相应的二苯氨基化合物是光学稳定的。
• One-pot synthesis of 2,4,5-trisubstituted oxazoles from N-acyl amino acids by a combination of cyclodehydration with N,N′-diisopropylcarbodiimide and Wittig olefination
  作者：Wenhua Huang、Guangping Dong、Zumureti Mijiti

  DOI：10.1016/j.tet.2011.12.004

  日期：2012.1

  By a combination of cyclodehydration of N-acyl amino acids with N,N′-diisopropylcarbodiimide (DIC) and non-classical Wittig olefination of the resultant 5(4H)-oxazolones with Ph3PCHCN and Ph3PCHCOOEt, 5-oxazoleacetonitriles and 5-oxazoleacetates were synthesized in one-pot in 41–85% and 57–70% yields, respectively.

  通过环化脱水的的组合ñ -酰基氨基酸与Ñ，Ñ '-diisopropylcarbodiimide（DIC）和所得到的5（4的非经典Wittig烯ħ）-oxazolones的Ph 3 P CHCN且Ph 3 P CHCOOEt，5-一锅合成恶唑乙腈和5-恶唑乙酸盐，产率分别为41-85％和57-70％。
• Pd-Catalyzed Asymmetric Hydroalkylation of 1,3-Dienes: Access to Unnatural α-Amino Acid Derivatives Containing Vicinal Quaternary and Tertiary Stereogenic Centers
  作者：Zongpeng Zhang、Fan Xiao、Hui-Min Wu、Xiu-Qin Dong、Chun-Jiang Wang

  DOI：10.1021/acs.orglett.9b04341

  日期：2020.1.17

  α-quaternary α-amino acid derivatives bearing contiguous quaternary and tertiary stereogenic centers in good yields with exclusive regioselectivity and excellent stereoselective control (up to 92% yield, >20:1 dr, and >99% ee). The scale-up catalytic asymmetric hydroalkylation was performed well without loss of reactivity and stereoselectivities, which exhibited great potential application. The synthetic utility

  首次成功开发了Pd-膦基恶唑啉（Pd-PHOX）催化的1，3-二烯与a内酯的不对称加氢烷基化反应，提供了具有连续四级和三级立体中心的各种对映体富集的α-季铵α-氨基酸衍生物，且收率高。独特的区域选择性和出色的立体选择性控制（高达92％的收率，> 20：1 dr和> 99％ee）。在不损失反应性和立体选择性的情况下，按比例放大的催化不对称加氢烷基化反应进行得很好，具有很大的潜在应用前景。通过产品转化来获得其他生物学上重要的化合物，例如手性β-氨基醇和α-季环状α-氨基酸衍生物，证明了当前方法的合成效用。
• Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and <i>N</i>,<i>O</i>-Acetal Derivatives
  作者：Tianli Wang、Zhaoyuan Yu、Ding Long Hoon、Claire Yan Phee、Yu Lan、Yixin Lu

  DOI：10.1021/jacs.5b10524

  日期：2016.1.13

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.
• Diastereochemical Diversity of Imidazoline Scaffolds via Substrate Controlled TMSCl Mediated Cycloaddition of Azlactones
  作者：Vasudha Sharma、Jetze J. Tepe

  DOI：10.1021/ol052118w

  日期：2005.10.1

  We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.