methyl 2-((tert-butoxycarbonyl)amino)-2-(4-fluorophenyl)acetate | 1273585-65-1

• 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 2-((tert-butoxycarbonyl)amino)-2-(4-fluorophenyl)acetate
• 英文别名: Methyl 2-tert-butyloxycarbonylamino-2-(4-fluorophenyl)acetate；methyl 2-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 1273585-65-1
• 化学式: C₁₄H₁₈FNO₄
• 分子量: 283.3
• InChiKey: RQCIVEMUMSZNIR-UHFFFAOYSA-N

物化性质

• 沸点：
  385.2±37.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-((tert-butoxycarbonyl)amino)-2-(4-fluorophenyl)acetate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到tert-butyl (1-(4-fluorophenyl)-2-(hydroxyamino)-2-oxoethyl)carbamate
  参考文献：
  名称：

  [EN] NOVEL AMINOPEPTIDASE INHIBITORS AND METHODS OF USE
  [FR] NOUVEAUX INHIBITEURS D'AMINOPEPTIDASE ET PROCÉDÉS D'UTILISATION

  摘要：

  一种含有生物芳基、羟肟酸基核的氨基肽酶抑制剂化合物，其化学式为：其中X为5或6元环，并包括其药用可接受的盐和溶剂化合物。

  公开号：

  WO2017008101A1
• 作为产物：
  描述：

  DL-4-氟苯甘氨酸 在 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 methyl 2-((tert-butoxycarbonyl)amino)-2-(4-fluorophenyl)acetate
  参考文献：
  名称：

  [EN] NOVEL AMINOPEPTIDASE INHIBITORS AND METHODS OF USE
  [FR] NOUVEAUX INHIBITEURS D'AMINOPEPTIDASE ET PROCÉDÉS D'UTILISATION

  摘要：

  一种含有生物芳基、羟肟酸基核的氨基肽酶抑制剂化合物，其化学式为：其中X为5或6元环，并包括其药用可接受的盐和溶剂化合物。

  公开号：

  WO2017008101A1

文献信息

• One-Pot Synthesis of α-Amino Acids from CO₂ Using a Bismetal Reagent with Si–B Bond
  作者：Tsuyoshi Mita、Jianyang Chen、Masumi Sugawara、Yoshihiro Sato

  DOI：10.1021/ol302952r

  日期：2012.12.21

  TsOH·H2O, precursors of N-Boc-imines can be converted into the corresponding α-aryl or α-alkenyl glycine derivatives under gaseous CO2 in moderate-to-high yields with a single operation. α-Isobutenyl glycine thus obtained can be further derivatized into various types of α-amino acids including N-Boc-leucine, serine, and glycine derivatives in short steps.

  在1.1当量的PhMe 2 Si-Bpin，5当量的CsF和20摩尔％的TsOH·H 2 O存在下，N -Boc-亚胺的前体可以转化为相应的α-芳基或α-烯基甘氨酸一次操作即可在气态CO 2下以中等至高收率得到各种衍生物。由此获得的α-异丁烯基甘氨酸可以在短时间内进一步衍生为各种类型的α-氨基酸，包括N -Boc-亮氨酸，丝氨酸和甘氨酸衍生物。
• One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis
  作者：Tsuyoshi Mita、Jianyang Chen、Masumi Sugawara、Yoshihiro Sato

  DOI：10.1002/anie.201006422

  日期：2011.2.7

  It′s a gas: A novel one‐pot process for the synthesis of α‐amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield

  它是一种气体：已开发出一种新颖的单罐方法，该方法使用CO 2气体作为碳源，从亚胺当量合成α-氨基酸。通过TMSSnBu 3和CsF的试剂结合使该反应成为可能（参见方案）。在这些条件下，在同一烧瓶中进行了三个连续的反应（亚胺形成，甲氧基化和羧化），以最高79％的收率得到产物。Boc =叔丁氧羰基，TMS =三甲基甲硅烷基。
• Potent dual inhibitors of Plasmodium falciparum M1 and M17 aminopeptidases through optimization of S1 pocket interactions
  作者：Nyssa Drinkwater、Natalie B. Vinh、Shailesh N. Mistry、Rebecca S. Bamert、Chiara Ruggeri、John P. Holleran、Sasdekumar Loganathan、Alessandro Paiardini、Susan A. Charman、Andrew K. Powell、Vicky M. Avery、Sheena McGowan、Peter J. Scammells

  DOI：10.1016/j.ejmech.2016.01.015

  日期：2016.3

  Malaria remains a global health problem, and though international efforts for treatment and eradication have made some headway, the emergence of drug-resistant parasites threatens this progress. Antimalarial therapeutics acting via novel mechanisms are urgently required. Plasmodium falciparum M1 and M17 are neutral aminopeptidases which are essential for parasite growth and development. Previous work in our group has identified inhibitors capable of dual inhibition of PfA-M1 and PfA-M17, and revealed further regions within the protease S1 pockets that could be exploited in the development of ligands with improved inhibitory activity. Herein, we report the structure-based design and synthesis of novel hydroxamic acid analogues that are capable of potent inhibition of both PfA-M1 and PfA-M17. Furthermore, the developed compounds potently inhibit Pf growth in culture, including the multi-drug resistant strain Dd2. The ongoing development of dual PIA-M1/PfA-M17 inhibitors continues to be an attractive strategy for the design of novel antimalarial therapeutics. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide
  作者：Tsuyoshi Mita、Masumi Sugawara、Hiroyuki Hasegawa、Yoshihiro Sato

  DOI：10.1021/jo202597p

  日期：2012.3.2

  Incorporation reactions of carbon dioxide (CO2) with N-Boc-alpha\-amido and a-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected alpha-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. alpha-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of alpha-tertiary and alpha-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-alpha-amido stannanes was transferred with up to 90% inversion of configuration at 100 degrees C.