2-(p-methoxyphenyl)-5-methoxyoxazole | 67567-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(p-methoxyphenyl)-5-methoxyoxazole
• 英文别名: 5-methoxy-2-(4-methoxyphenyl)oxazole；Oxazole, 5-methoxy-2-(4-methoxyphenyl)-；5-methoxy-2-(4-methoxyphenyl)-1,3-oxazole
• CAS: 67567-57-1
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: YGXKDXZTWZTMEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-(p-methoxyphenyl)-5-methoxyoxazole 在 四氯化锡 、 钯 氢气 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， -20.0 ℃ 、1.01 MPa 条件下， 反应 26.0h， 生成 methyl (4S,5S,1'S)-5-<1'-(hydroxy)ethyl>-2-(p-methoxyphenyl)-2-oxazoline-4-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Synthesis of 2-Oxazoline-4-carboxylates by Formal [3 + 2] Cycloadditions of a 5-Alkoxyoxazole with .alpha.-Alkoxy Aldehydes Catalyzed by Tin(IV) Chloride

  摘要：

  The formal [3 + 2] cycloaddition of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2(S)-(benzyloxy)propanal and 2(S)-[(tert-butyldimethylsilyl)oxy]propanal in the presence of tin(IV) chloride gave cis-(4R,5S,1'S)- and trans-(4S,5S,1'S)-5-(1'-alkoxyethyl)-4-(methoxycarbonyl)-2-(p-methoxyphenyl)-2-oxazolines with high diastereoselectivity (94 and 92% selectivity, respectively). A similar reaction of 5-methoxy-2-(p-methoxyphenyl) oxazole with 2,3-di-O-benzyl-D-glyceraldehyde gave methyl cis-(4S,5R,1'R)-2-(p-methoxyphenyl)-5-[1',2'-bis(benzyloxy)ethyl]-2-oxazoline-4-carboxylate with high diastereoselectivity (>95% selectivity), and the latter was easily converted to biologically important chiral 2-amino-1,3,4,5-tetrol derivatives.

  DOI：

  10.1021/jo00091a023
• 作为产物：
  描述：

  甘氨酸,N-[(4-甲氧苯基)亚甲基]-,甲基酯 在 碘苯二乙酸 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到2-(p-methoxyphenyl)-5-methoxyoxazole
  参考文献：
  名称：

  Xia, Journal of Chemical Research - Part S, 2000, # 8, p. 382 - 383

  摘要：

  DOI：

文献信息

• Evolution of the Total Syntheses of Ustiloxin Natural Products and Their Analogues
  作者：Pixu Li、Cory D. Evans、Yongzhong Wu、Bin Cao、Ernest Hamel、Madeleine M. Joullié

  DOI：10.1021/ja710363p

  日期：2008.2.1

  synthetically challenging chiral tertiary alkyl-aryl ether linkage. The first total synthesis of ustiloxin D was achieved in 31 linear steps using an S(N)Ar reaction. An NOE study of this synthetic product showed that ustiloxin D existed as a single atropisomer. Subsequently, highly concise and convergent syntheses of ustiloxins D and F were developed by utilizing a newly discovered ethynyl aziridine ring-opening

  Ustiloxins AF 是抗有丝分裂杂环肽，含有 13 元环状核心结构，具有合成上具有挑战性的手性叔烷基芳基醚键。使用 S(N)Ar 反应，通过 31 个线性步骤实现了 ustiloxin D 的首次全合成。该合成产品的 NOE 研究表明乌司洛辛 D 作为单一阻转异构体存在。随后，利用新发现的乙炔基氮丙啶开环反应，以 15 个步骤的最长线性序列开发了乌斯蒂洛辛 D 和 F 的高度简洁和收敛的合成方法。该方法进一步优化以实现更好的大环内酰胺化策略。通过第二代制备了乌斯蒂洛辛D、F和8个类似物（14-MeO-乌斯蒂洛辛D、4个C-6位氨基酸残基不同的类似物、以及3个(9R,10S)-表乌斯蒂洛辛类似物）路线。对这些化合物作为微管蛋白聚合抑制剂的评估表明，C-6 位的变化在一定程度上是可以容忍的。相反，C-9 甲氨基的 S 构型和游离酚羟基对于抑制微管蛋白聚合至关重要。
• Pd-Catalyzed C4-Olefination of Oxazoles via C–H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives
  作者：Sunliang Cui、Lukasz Wojtas、Jon C. Antilla

  DOI：10.1021/ol201865h

  日期：2011.10.7

  A Pd-catalyzed C4-olefination of oxazoles via C–H bond activation under mild conditions was achieved. The reaction was shown to be general over a range of substrates. New protocols for the divergent transformation of these products to provide functionalized amino alcohol and amino acid derivatives have also been established.

  在温和的条件下，通过C–H键的活化，实现了Pd催化的恶唑的C4烯化反应。在一系列底物上显示该反应是普遍的。还建立了用于这些产物的发散转化以提供官能化的氨基醇和氨基酸衍生物的新方案。
• 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。
• Abnormal Diels–Alder Reaction of 5-Alkoxyoxazoles with Tetracyanoethylene and X-Ray Crystal Structure of an Adduct
  作者：Toshikazu Ibata、Yasushi Isogami、Hiroyuki Nakawa、Hatsue Tamura、Hiroyuki Suga、Xiaolan Shi、Hiroki Fujieda

  DOI：10.1246/bcsj.65.1771

  日期：1992.7

  2] cycloadducts through oxazole ring opening. Zwitterionic mechanisms were proposed on the basis of the solvent effect on the reaction. The molecular structure of 2-isopropyl-substituted product was determined by means of X-ray crystallography. Crystals of the cycloadduct are orthorhombic with space group Pcab having unit-cell dimensions of a = 17.998 (2), b = 27.188 (6), c = 15.833 (3) A, and Z = 16

  2-烷基-或2-芳基-取代的5-甲氧基-4-(对硝基苯基)恶唑与四氰基乙烯反应得到5-取代的3,3,4,4-四氰基-2-(对硝基苯基)甲酯)-3,4-二氢-2H-吡咯-2-羧酸作为正式的[3 + 2]环加合物通过恶唑开环。基于溶剂对反应的影响提出了两性离子机理。2-异丙基取代产物的分子结构通过X-射线晶体学确定。环加合物的晶体是正交的，空间群 Pcab 的晶胞尺寸为 a = 17.998 (2)、b = 27.188 (6)、c = 15.833 (3) A 和 Z = 16，其中包含两个晶体学独立的分子。对于 4629 次观察到的反射，最终的 R 值为 0.070。
• Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles
  作者：Jialin Xie、Yuanqiong Huang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.7b02767

  日期：2017.11.17

  An atom-economical method for accessing tetrasubstituted 4,5-biscarbonylimidazoles by reaction between glycine derivatives and 5-alkoxyoxazoles is reported. The method, which involves a copper-catalyzed aerobic oxidative [2 + 3] cyclization/aromatization cascade process, starts from readily available and inexpensive materials, uses molecular oxygen as a co-oxidant, and has a broad substrate scope.

  报道了通过甘氨酸衍生物和5-烷氧基恶唑之间的反应获得四取代的4，5-双羰基咪唑的原子经济方法。该方法涉及铜催化的好氧氧化[2 + 3]环化/芳香化反应级联过程，从容易获得且廉价的材料开始，使用分子氧作为助氧化剂，具有广泛的底物范围。