methyl 3-(4-iodophenyl)-2-(2,2,2-trifluoroacetamido)propanoate | 1262841-34-8

• 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 3-(4-iodophenyl)-2-(2,2,2-trifluoroacetamido)propanoate
• 英文别名: rac-2-(2,2,2-trifluoroacetylamino)-3-(4-iodophenyl)propionic acid methyl ester；Methyl 3-(4-iodophenyl)-2-[(2,2,2-trifluoroacetyl)amino]propanoate；methyl 3-(4-iodophenyl)-2-[(2,2,2-trifluoroacetyl)amino]propanoate
• CAS: 1262841-34-8
• 化学式: C₁₂H₁₁F₃INO₃
• 分子量: 401.124
• InChiKey: GKRQVLQVCCOCRF-UHFFFAOYSA-N

物化性质

• 沸点：
  400.4±45.0 °C(Predicted)
• 密度：
  1.695±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氯乙酸叔丁酯 、 methyl 3-(4-iodophenyl)-2-(2,2,2-trifluoroacetamido)propanoate 在 乙二醇二甲醚溴化镍 、 二氢吡啶 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 N,N-二异丙基乙胺 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 3-(4-(2-(tert-butoxy)-2-oxoethyl)phenyl)-2-(2,2,2-trifluoroacetamido)propanoate
  参考文献：
  名称：

  使用金属光氧化还原催化的肽的后期磷酸酪氨酸模拟功能化

  摘要：

  获得磷酸酪氨酸 (pTyr) 模拟物需要多步合成，因此将这些模拟物后期掺入肽中是不可行的。在这里，我们使用 4-卤代苯丙氨酸开发和使用金属光氧化还原催化，一步提供各种受保护的 pTyr 模拟物。该方法显示出对常见保护基团的耐受性，并适用于受保护和未受保护肽以及具有生物相关性的肽的后期 pTyr 模拟修饰。

  DOI：

  10.1021/acs.orglett.1c01200
• 作为产物：
  描述：

  methyl 3-(4-iodophenyl)-2-methoxy-2-(2,2,2-trifluoroacetamido)propanoate 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以43%的产率得到methyl 3-(4-iodophenyl)-2-(2,2,2-trifluoroacetamido)propanoate
  参考文献：
  名称：

  The Heck–Matsuda arylation of 2-hetero-substituted acrylates

  摘要：

  The Heck-Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd-2(dba)(3) as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were subjected to an elimination/reduction protocol to obtain the corresponding N,O-protected phenylalanine derivatives. A one-pot procedure for the preparation of phenylalanine derivatives from 2-aza-substituted acrylates is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.132

文献信息

• Synthesis and SERCA activities of structurally simplified cyclopiazonic acid analogues
  作者：Sheng Yao、Daniel Gallenkamp、Katharina Wölfel、Bettina Lüke、Michael Schindler、Jürgen Scherkenbeck

  DOI：10.1016/j.bmc.2011.06.001

  日期：2011.8

  terpenoid artemisinin. Due to its less complex structure CPA represents an attractive lead structure for the development of novel antimalarial drugs or for applications in the field of plant protection. We report here the first syntheses of structurally simplified CPA fragments and discuss their SERCA activities on the basis of published crystal structures of CPA–SERCA complexes.

  吲哚生物碱环吡唑酸（CPA）是除抗癌药thapsigargin和抗血浆类萜类青蒿素外，为数不多的已知的肌醇内质网Ca 2+ -ATPase（SERCA）纳摩尔抑制剂之一。由于其结构不那么复杂，CPA代表了一种引人注目的铅结构，可用于开发新型抗疟药或用于植物保护领域。我们在这里报告结构简化的CPA片段的第一个合成，并在已发表的CPA-SERCA复合物晶体结构的基础上讨论了它们的SERCA活性。
• Late Stage Phosphotyrosine Mimetic Functionalization of Peptides Employing Metallaphotoredox Catalysis
  作者：Hao Chen、Runyu Mao、Martin Brzozowski、Nghi H. Nguyen、Brad E. Sleebs

  DOI：10.1021/acs.orglett.1c01200

  日期：2021.6.4

  requires multistep syntheses, and therefore late stage incorporation of these mimetics into peptides is not feasible. Here, we develop and employ metallaphotoredox catalysis using 4-halogenated phenylalanine to afford a variety of protected pTyr mimetics in one step. This methodology was shown to be tolerant of common protecting groups and applicable to the late stage pTyr mimetic modification of protected

  获得磷酸酪氨酸 (pTyr) 模拟物需要多步合成，因此将这些模拟物后期掺入肽中是不可行的。在这里，我们使用 4-卤代苯丙氨酸开发和使用金属光氧化还原催化，一步提供各种受保护的 pTyr 模拟物。该方法显示出对常见保护基团的耐受性，并适用于受保护和未受保护肽以及具有生物相关性的肽的后期 pTyr 模拟修饰。
• The Heck–Matsuda arylation of 2-hetero-substituted acrylates
  作者：Francisco de Azambuja、Carlos Roque Duarte Correia

  DOI：10.1016/j.tetlet.2010.10.132

  日期：2011.1

  The Heck-Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd-2(dba)(3) as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were subjected to an elimination/reduction protocol to obtain the corresponding N,O-protected phenylalanine derivatives. A one-pot procedure for the preparation of phenylalanine derivatives from 2-aza-substituted acrylates is presented. (C) 2010 Elsevier Ltd. All rights reserved.