5-(4-bromo-2-methoxyphenyl)oxazole | 1091618-41-5

• 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-(4-bromo-2-methoxyphenyl)oxazole
• 英文别名: 5-(4-Bromo-2-methoxyphenyl)oxazole；5-(4-bromo-2-methoxyphenyl)-1,3-oxazole
• CAS: 1091618-41-5
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: DTUKOCCOHDYOGT-UHFFFAOYSA-N

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：
  0.1
• 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-(4-bromo-2-methoxyphenyl)oxazole 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 copper(l) iodide 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以97%的产率得到C₁₀H₈INO₂
  参考文献：
  名称：

  Mycophenolic acid analogs with a modified metabolic profile

  摘要：

  Mycophenolic acid (MPA), a clinically used immunosuppressant, is extensively metabolized into an inactive C7-glucuronide and removed from circulation. To circumvent the metabolic liability imposed by the C7-hydroxyl group, we have designed a series of hybrid MPA analogs based on the pharmacophores present in MPA and new generations of inosine monophosphate dehydrogenase (IMPDH) inhibitors. The synthesis of MPA analogs has been accomplished by an allylic substitution of a common lactone. Biological evaluations of these analogs and a preliminary structure-activity relationship (SAR) are presented. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.062
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 4-溴-2-甲氧基苯甲醛 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以83 %的产率得到5-(4-bromo-2-methoxyphenyl)oxazole
  参考文献：
  名称：

  通过 1,3,2-二氮杂磷烯催化还原不对称 Aza-Mislow-Evans 重排**

  摘要：

  1,3,2-二氮杂磷烯催化的手性N-亚磺酰丙烯酰胺的三步级联转化，包括共轭还原、对映特异性 [2,3]-sigmatropic aza-Mislow-Evans 重排和随后的 S−O 键还原裂解提供了获得具有合成价值的富含对映体的 α-羟基酰胺的途径。在非常温和的条件下，以高产率和高对映选择性获得各种 α-羟基酰胺。

  DOI：

  10.1002/anie.202301076

文献信息

• Mycophenolic acid analogs with a modified metabolic profile
  作者：Liqiang Chen、Daniel J. Wilson、Nicholas P. Labello、Hiremagalur N. Jayaram、Krzysztof W. Pankiewicz

  DOI：10.1016/j.bmc.2008.08.062

  日期：2008.10

  Mycophenolic acid (MPA), a clinically used immunosuppressant, is extensively metabolized into an inactive C7-glucuronide and removed from circulation. To circumvent the metabolic liability imposed by the C7-hydroxyl group, we have designed a series of hybrid MPA analogs based on the pharmacophores present in MPA and new generations of inosine monophosphate dehydrogenase (IMPDH) inhibitors. The synthesis of MPA analogs has been accomplished by an allylic substitution of a common lactone. Biological evaluations of these analogs and a preliminary structure-activity relationship (SAR) are presented. (c) 2008 Elsevier Ltd. All rights reserved.
• Reductive Asymmetric Aza‐Mislow‐Evans Rearrangement by 1,3,2‐Diazaphospholene Catalysis**
  作者：Guoting Zhang、Nicolai Cramer

  DOI：10.1002/anie.202301076

  日期：——

  A 1,3,2-diazaphospholene-catalyzed three-step cascade transformation of chiral N-sulfinyl acrylamides comprised of a conjugate reduction, enantiospecific [2,3]-sigmatropic aza-Mislow-Evans rearrangement, and subsequent S−O bond reductive cleavage provides access to synthetically valuable enantio-enriched α-hydroxy amides. Various α-hydroxy amides are obtained in good yields and high enantioselectivities

  1,3,2-二氮杂磷烯催化的手性N-亚磺酰丙烯酰胺的三步级联转化，包括共轭还原、对映特异性 [2,3]-sigmatropic aza-Mislow-Evans 重排和随后的 S−O 键还原裂解提供了获得具有合成价值的富含对映体的 α-羟基酰胺的途径。在非常温和的条件下，以高产率和高对映选择性获得各种 α-羟基酰胺。