methyl 4-cyano-3,5-dimethylbenzoate | 1001055-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-cyano-3,5-dimethylbenzoate
• 英文别名: Methyl 4-cyano-3,5-dimethylbenzoate
• CAS: 1001055-67-9
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: NBYYSQWCZUFTBE-UHFFFAOYSA-N

物化性质

• 沸点：
  333.3±30.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-cyano-3,5-dimethylbenzoate 在 Li[H₃B-pyrrolidino] 作用下， 以 四氢呋喃 为溶剂， 生成 4-hydroxymethyl-2,6-dimethylbenzenenitrile
  参考文献：
  名称：

  Design and synthesis of potent amido- and benzyl-substituted cis-3-amino-4-(2-cyanopyrrolidide)pyrrolidinyl DPP-IV inhibitors

  摘要：

  The cis-3-amino-4-(2-cyanopyrrolidide)-pyrrolidine template has been shown to afford low nanomolar inhibitors of human DPP-IV that exhibit a robust PK/PD profile. An X-ray co-crystal structure of 5 confirmed the proposed mode of binding. The potent single digit DPP-IV inhibitor 53 exhibited a preferred PK/PD profile in preclinical animal models and was selected for additional profiling.

  DOI：

  10.1016/j.bmcl.2007.10.063
• 作为产物：
  描述：

  4-溴-3,5-二甲基苯甲酸甲酯 、 氰化亚铜 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-cyano-3,5-dimethylbenzoate
  参考文献：
  名称：

  Design and synthesis of potent amido- and benzyl-substituted cis-3-amino-4-(2-cyanopyrrolidide)pyrrolidinyl DPP-IV inhibitors

  摘要：

  The cis-3-amino-4-(2-cyanopyrrolidide)-pyrrolidine template has been shown to afford low nanomolar inhibitors of human DPP-IV that exhibit a robust PK/PD profile. An X-ray co-crystal structure of 5 confirmed the proposed mode of binding. The potent single digit DPP-IV inhibitor 53 exhibited a preferred PK/PD profile in preclinical animal models and was selected for additional profiling.

  DOI：

  10.1016/j.bmcl.2007.10.063

文献信息

• Modular Dual-Tasked C–H Methylation via the Catellani Strategy
  作者：Qianwen Gao、Yong Shang、Fuzhen Song、Jinxiang Ye、Ze-Shui Liu、Lisha Li、Hong-Gang Cheng、Qianghui Zhou

  DOI：10.1021/jacs.9b07857

  日期：2019.10.9

  We report a dual-tasked methylation based on cooperative palladium/norbornene catalysis. Readily available (hetero)aryl halides (39 iodides and 4 bromides) and inexpensive MeOTs or trimethylphosphate are utilized as the substrates and meth-ylating reagent, respectively. Six types of ipso terminations can modularly couple with this ortho C-H methylation to consti-tute a versatile methylation toolbox

  我们报告了基于协同钯/降冰片烯催化的双任务甲基化。容易获得的（杂）芳基卤化物（39 个碘化物和 4 个溴化物）和廉价的 MeOT 或磷酸三甲酯分别用作底物和甲基化试剂。六种类型的 ipso 末端可以与这种邻位 CH 甲基化模块化耦合，构成一个通用的甲基化工具箱，用于制备多样化的甲基化芳烃。该工具箱具有廉价的甲基来源、出色的官能团耐受性、简单的反应程序和可扩展性。重要的是，通过切换到相应的试剂 CD3OT 或 13CH3OT，它可以顺利地扩展到同位素标记的甲基化。此外，该工具箱可用于具有完全立体保留的生物相关底物的后期修饰。
• Design and synthesis of potent amido- and benzyl-substituted cis-3-amino-4-(2-cyanopyrrolidide)pyrrolidinyl DPP-IV inhibitors
  作者：J.W. Corbett、K. Dirico、W. Song、B.P. Boscoe、S.D. Doran、D. Boyer、X. Qiu、M. Ammirati、M.A. VanVolkenburg、R.K. McPherson、J.C. Parker、E.D. Cox

  DOI：10.1016/j.bmcl.2007.10.063

  日期：2007.12

  The cis-3-amino-4-(2-cyanopyrrolidide)-pyrrolidine template has been shown to afford low nanomolar inhibitors of human DPP-IV that exhibit a robust PK/PD profile. An X-ray co-crystal structure of 5 confirmed the proposed mode of binding. The potent single digit DPP-IV inhibitor 53 exhibited a preferred PK/PD profile in preclinical animal models and was selected for additional profiling.