5-Methoxy-4-methyl-2-phenyl-oxazol | 31698-99-4

• 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-4-methyl-2-phenyl-oxazol
• 英文别名: 2-Phenyl-4-methyl-5-methoxy-oxazol；5-methoxy-4-methyl-2-phenyl-1,3-oxazole
• CAS: 31698-99-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: GBELEWQAIMXXCE-UHFFFAOYSA-N

物化性质

• 沸点：
  304.3±34.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-4-methyl-2-phenyl-oxazol 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氘代苯 、 乙腈 为溶剂， 反应 50.5h， 生成 2-carbomethoxy-4-phenyl-2,3,5-trimethylthiazolidine
  参考文献：
  名称：

  Reaction of thioaldehydes with 5-alkoxyoxazoles. A route to 3-thiazolines

  摘要：

  DOI：

  10.1021/jo00255a004
• 作为产物：
  描述：

  2-Azidopropansaeure-methylester 、 苯甲酰溴 生成 5-Methoxy-4-methyl-2-phenyl-oxazol
  参考文献：
  名称：

  Reaktionen mit phosphororganischen Verbindungen, 26. Mitt.: Ein neuartiges Syntheseprinzip f�r Oxazole

  摘要：

  DOI：

  10.1007/bf00909226

文献信息

• Photocycloadditions of substituted oxazoles with isoquinoline-1,3,4-trione—chemo-, regio-, diastereoselectivities and transformation of the photocycloadducts
  作者：Cheng-mei Huang、Heng Jiang、Ru-zhi Wang、Ching Kheng Quah、Hoong-Kun Fun、Yan Zhang

  DOI：10.1039/c3ob40645h

  日期：——

  Photoreactions of isoquinoline-1,3,4-triones and oxazoles with different substituents were found to give different chemo-, regio- and diastereoselectivities. The substituent at the C5 on the oxazole ring showed great influence on the chemoselectivity of the photoreaction as well as on the transformation of the photocycloadducts. The 2-methyl-5-methoxyoxazoles reacted with isoquinoline-1,3,4-triones rapidly and gave spirooxetanes with high regio- and diastereo-selectivity. Diastereoselectivity in the reaction of 2-phenyl-5-methoxyoxazoles with isoquinoline-1,3,4-triones was relevant to the substituent on the 4-position on the oxazole ring. Replacement of the 5-methoxy group with 5-methyl or 5-phenyl resulted in significant decrease on the reactivity of the oxazole as well as change on the diastereoselectivity in photocycloaddition with isoquinoline-1,3,4-triones. Acid-mediated transformations of the photocycloadduct spirooxetanes was found to give different type of products including β-hydroxy-α-aminocarbonyl compounds and spiroisoquinolineoxazolines under different reaction conditions. Substituents on the spirooxetanes as well as the type and amount of acid used in the reaction played important roles in determining the type and diastereoselectivity of the products in the transformations.

  不同取代基的异喹啉-1,3,4-三酮和噁唑的光反应发现具有不同的化学选择性、区域选择性和非对映选择性。噁唑环C5处的取代基对光反应的化学选择性以及光环加成产物的转化有很大影响。2-甲基-5-甲氧基噁唑与异喹啉-1,3,4-三酮反应迅速，产生具有高区域选择性和非对映选择性的螺氧烷。2-苯基-5-甲氧基噁唑与异喹啉-1,3,4-三酮的反应中的非对映选择性与噁唑环4位的取代基相关。用5-甲基或5-苯基替换5-甲氧基过程显著降低了噁唑的反应活性，并改变了与异喹啉-1,3,4-三酮的光环加成反应中的非对映选择性。酸介导的光环加成产物螺氧烷的转化在不同反应条件下发现可以生成不同类型的产物，包括β-羟基-α-氨基碳基化合物和螺异喹啉噁唑啉。螺氧烷上的取代基以及反应中使用的酸的类型和量在确定产物的类型和非对映选择性方面起着重要作用。
• 4-Oxazoline route to stabilized azomethine ylides. Controlled reduction of oxazolium salts
  作者：E. Vedejs、J. W. Grissom

  DOI：10.1021/ja00218a038

  日期：1988.5

  Etude, en particulier de l'effet des substituants de l'oxazole de depart sur les produits obtenus

  练习曲, en particulier de l'effet des substituants de l'oxazole de leave sur les produits obtenus
• Photosensitized Oxidation of Furans; Part 17:¹A Simple Method for the Synthesis of 5-Hydroperoxyfuran-2(5<i>H</i>)-ones
  作者：M. Rosaria Iesce、Flavio Cermola、M. Liliana Graziano、Rachele Scarpati

  DOI：10.1055/s-1994-25610

  日期：——

  The 5-hydroperoxyfuran-2(5H)-ones 3 are synthesized by acid hydrolysis of the dihydrofurans 1 which are prepared in one-pot procedure by reaction of the corresponding furans 4 with singlet oxygen and methanol. The synthetic method has a wide range of applicability; however, compounds 3 unsubstituted at C-4 cannot be prepared since the corresponding dihydrofurans 1 are not formed.

  5-氢过氧呋喃-2(5H)-酮3是通过对二氢呋喃1进行酸水解合成的。这些二氢呋喃1是在一次性反应过程中，通过相应的呋喃4与单线态氧和甲醇反应制备的。该合成方法具有广泛的应用范围；然而，无法制备在C-4位上未经取代的化合物3，因为相应的二氢呋喃1不会形成。
• Graziano, M. Liliana; Iesce, M. Rosaria; Cermola, Flavio, Journal of the Chemical Society. Perkin transactions I, 1991, # 6, p. 1479 - 1484
  作者：Graziano, M. Liliana、Iesce, M. Rosaria、Cermola, Flavio、Cimminiello, Guido、Scarpati, Rachele

  DOI：——

  日期：——
• 3<i>H</i>-1,2,4-Dioxazoles from 1,3-Oxazoles
  作者：M. L. GRAZIANO、M. R. IESCE、A. CAROTENUTO、R. SCARPATI

  DOI：10.1055/s-1977-24482

  日期：——