methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoate | 176795-01-0

• 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: methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoate
• CAS: 176795-01-0
• 化学式: C₁₆H₂₀F₃NO₄
• 分子量: 347.334
• InChiKey: JRHLZJIOXBLLMJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 BOC-D-4-三氟甲基苯丙氨酸
  参考文献：
  名称：

  Discovery of pyrrolopyrimidine inhibitors of Akt

  摘要：

  The discovery and optimization of a series of pyrrolopyrimidine based protein kinase B (Pkb/Akt) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent inhibition of all three Akt isoforms and knockdown of phospho-PRAS40 levels in LNCaP cells and tumor xenografts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.053
• 作为产物：
  描述：

  methyl (Z)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]prop-2-enoate 在 [R,R-RhMe-Duphos] 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoate
  参考文献：
  名称：

  Discovery of pyrrolopyrimidine inhibitors of Akt

  摘要：

  The discovery and optimization of a series of pyrrolopyrimidine based protein kinase B (Pkb/Akt) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent inhibition of all three Akt isoforms and knockdown of phospho-PRAS40 levels in LNCaP cells and tumor xenografts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.053

文献信息

• Electronically Ambivalent Hydrodefluorination of Aryl‐CF ₃ groups enabled by Electrochemical Deep‐Reduction on a Ni Cathode
  作者：John R. Box、Mickaël E. Avanthay、Darren L. Poole、Alastair J. J. Lennox

  DOI：10.1002/anie.202218195

  日期：2023.3.13

  We report a general procedure for the direct mono- and di-hydrodefluorination of ArCF3 compounds. Exploiting the tunability of electrochemistry and the selectivity enabled by a Ni cathode, the deep reduction garners high selectivity with good to excellent yields up to gram scale. The late-stage peripheral editing of CF3 feedstocks to construct fluoromethyl moieties will aid the rapid diversification

  我们报告了ArCF 3化合物直接单加氢和双加氢脱氟的一般程序。利用电化学的可调性和镍阴极实现的选择性，深度还原获得了高选择性，并且产量高达克级。用于构建氟甲基部分的 CF 3原料的后期外围编辑将有助于先导化合物和化合物库的快速多样化。
• A selective and mild electrochemical defluorinative carboxylation for late-stage C(sp³)–F bond functionalization
  作者：Subhojit Mondal、Soumik Sarkar、Jason W. Wang、Michael W. Meanwell

  DOI：10.1039/d3gc03387b

  日期：——

  defluorinative carboxylation of trifluoromethyl (hetero)arenes, and trifluoromethyl-acetates and -acetamides, for accessing their highly valuable α,α-difluorocarboxylic acid analogues. Given the immense synthetic versatility of carboxylic acids, our new protocol may become a useful tool for accessing novel fluorinated analogues in drug design and agrochemical development.

  我们报告了三氟甲基（杂）芳烃、三氟甲基乙酸酯和三氟乙酰胺的电化学脱氟羧化的第一个通用方案，以获取其高价值的α,α-二氟羧酸类似物。鉴于羧酸的巨大合成多功能性，我们的新方案可能成为在药物设计和农用化学品开发中获取新型氟化类似物的有用工具。
• Discovery of pyrrolopyrimidine inhibitors of Akt
  作者：James F. Blake、Nicholas C. Kallan、Dengming Xiao、Rui Xu、Josef R. Bencsik、Nicholas J. Skelton、Keith L. Spencer、Ian S. Mitchell、Richard D. Woessner、Susan L. Gloor、Tyler Risom、Stefan D. Gross、Matthew Martinson、Tony H. Morales、Guy P.A. Vigers、Barbara J. Brandhuber

  DOI：10.1016/j.bmcl.2010.08.053

  日期：2010.10

  The discovery and optimization of a series of pyrrolopyrimidine based protein kinase B (Pkb/Akt) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent inhibition of all three Akt isoforms and knockdown of phospho-PRAS40 levels in LNCaP cells and tumor xenografts. (C) 2010 Elsevier Ltd. All rights reserved.