4-(4-chloro-benzyl)-2-phenyl-4H-oxazol-5-one | 221071-22-3

• 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: 4-(4-chloro-benzyl)-2-phenyl-4H-oxazol-5-one
• 英文别名: 4-(4-chlorobenzyl)-2-phenyloxazol-5(4H)-one；4-[(4-chlorophenyl)methyl]-2-phenyl-4H-1,3-oxazol-5-one
• CAS: 221071-22-3
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: DUWAPQXXTCWWBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  聚合甲醛 、 4-(4-chloro-benzyl)-2-phenyl-4H-oxazol-5-one 在 吡啶 作用下， 以 水 为溶剂， 反应 16.0h， 以63%的产率得到N-(5-(4-chlorobenzyl)-4-oxo-1,3-dioxan-5-yl)benzamide
  参考文献：
  名称：

  Design and synthesis of 3-arylpyrrolidine-2-carboxamide derivatives as melanocortin-4 receptor ligands

  摘要：

  Based on 3-phenylpropionamides, a series of 3-arylpyrrolidine-2-carboxamide derivatives was designed and synthesized to study the effect of cyclizations as melanocortin-4 receptor ligands. It was found that the 2R, 3R-pyrrolidine isomer possessed the most potent affinity among the four stereoisomers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.125
• 作为产物：
  描述：

  苯甲酰氯 在 乙酸酐 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 28.17h， 生成 4-(4-chloro-benzyl)-2-phenyl-4H-oxazol-5-one
  参考文献：
  名称：

  通过2-（1-甲苯磺酰基烷基）苯酚生成的邻醌甲基化物，双官能方酰胺催化手性二氢香豆素的合成

  摘要：

  在碱性条件下成功开发了由2-（1-甲苯磺酰基烷基）-苯酚原位生成的双官能方酸酰胺催化的内酯和邻醌甲基化物的反应，可有效，温和地获得手性二氢香豆素。

  DOI：

  10.1039/c7cc01072a

文献信息

• Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives <i>via</i> desymmetrization of <i>p</i>-quinols with azlactones
  作者：Lihua Xie、Shunxi Dong、Qian Zhang、Xiaoming Feng、Xiaohua Liu

  DOI：10.1039/c8cc08985j

  日期：——

  3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved through BG-1·HBPh₄ catalyzed enantioselective Michael addition/lactonization cascade reaction of p-quinols with azlactones.

  通过 BG-1-HBPh4 催化对醌与氮内酯的对映选择性迈克尔加成/内酯化级联反应，获得了含有手性氨基酸残基的 3-氨基苯并呋喃-2,5-二酮。
• Catalytic asymmetric formal [3+2] cycloaddition of isatogens with azlactones to construct indolin-3-one derivatives
  作者：Lihua Xie、Yi Li、Shunxi Dong、Xiaoming Feng、Xiaohua Liu

  DOI：10.1039/d0cc06418a

  日期：——

  A number of enantioenriched indolin-3-one derivatives were readily obtained by chiral guanidine-catalyzed [3+2] cycloaddition of isatogens with azlactones.

  一些手性瓜尼丁催化的异丙基吲哚啉-3-酮衍生物通过异丙基吲哚啉与氮丙烯酮的手性[3+2]环加成反应轻松获得。
• Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols
  作者：Ji Zhou、Mao-Lin Wang、Xiang Gao、Guo-Fang Jiang、Yong-Gui Zhou

  DOI：10.1039/c7cc01072a

  日期：——

  A bifunctional squaramide-catalyzed reaction of azlactones and o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been succesfully developed under basic condition, providing an efficient and mild access to chiral dihydrocoumarins...

  在碱性条件下成功开发了由2-（1-甲苯磺酰基烷基）-苯酚原位生成的双官能方酸酰胺催化的内酯和邻醌甲基化物的反应，可有效，温和地获得手性二氢香豆素。
• Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives
  作者：Qijian Ni、Xuyang Wang、Fangfang Xu、Xiaoyun Chen、Xiaoxiao Song

  DOI：10.1039/d0cc00736f

  日期：——

  An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20 : 1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent

  已经成功开发了2-苯并噻唑啉与氮杂内酯之间的有机催化不对称多米诺骨牌曼尼希/环化反应。使用双功能方酰胺催化剂，这种正式的[4 + 2]环化反应具有良好的高收率和出色的立体选择性（高达99％ee，> 20：1 dr），提供了温和而温和的途径来接触带有相邻三级和三级的手性苯并噻唑并嘧啶第四纪立体成因中心。
• Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(<scp>iii</scp>)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction
  作者：Haipeng Hu、Yangbin Liu、Jing Guo、Lili Lin、Yali Xu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c4cc10343b

  日期：——

  An asymmetric inverse-electron-demand hetero-Diels-Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N'-dioxide-Sc(III) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96%

  通过使用手性N，N'-二氧化物-Sc（III）络合物作为催化剂，可以有效地实现邻醌甲基化物和between内酯之间的不对称逆电子需求异Diels-Alder反应，以产生潜在的药理活性二氢香豆素。在温和的反应条件下，以高收率获得具有优异的对映选择性和非对映选择性（高达94％收率，96％ee和> 19：1 dr）的所需产物。Operando IR和对照实验证实了一致的反应途径。