2,2,2-trifluoro-N-(2-hydroxyethyl)-N-methylacetamide | 245051-59-6

• 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: 2,2,2-trifluoro-N-(2-hydroxyethyl)-N-methylacetamide
• 英文别名: N-methyl-N-trifluoroacetyl ethanoloamine
• CAS: 245051-59-6
• 化学式: C₅H₈F₃NO₂
• 分子量: 171.119
• InChiKey: VTAULGOGEKXXHP-UHFFFAOYSA-N

物化性质

• 沸点：
  241.7±40.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-(2-hydroxyethyl)-N-methylacetamide 在 吡啶 、 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-N-methyl-N-trifluoroacetyl-2-aminoacetaldehyde-O-methyloxime
  参考文献：
  名称：

  Intramolecular Aziridination:  Decomposition of Diazoamides with Tethered Imino Bonds

  摘要：

  Of three possible mechanistic pathways, tethered oximino ethers react intramolecularly with diazoamides to produce a diazabicyclo[5.1.0]hexane aziridine containing skeleton. Several acyclic and cyclic templates were synthesized and reacted with rhodium catalysts to prepare their corresponding annulated aziridines. Anomalous behavior was discovered with the piperidine template, resulting in an aziridination occurring during the attempted diazo-transfer reaction, rather than the catalyzed carbenoid reaction.

  DOI：

  10.1021/ol990750h
• 作为产物：
  描述：

  (E,Z)-1,1,1-trifluoro-4-((2-hydroxyethyl)(methyl)amino)-4-(4-methoxyphenyl)but-3-en-2-one 以 乙醇 为溶剂， 反应 28.0h， 以56%的产率得到对甲氧基苯乙酮
  参考文献：
  名称：

  三氟乙酰基乙炔与β-氨基醇的反应。烯酮的合成和不寻常的断裂

  摘要：

  DOI：

  10.1016/j.jfluchem.2016.08.008

文献信息

• Method of preparing phosphoramidites
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06335439B1

  公开（公告）日：2002-01-01

  Improved methods for preparation of phosphoramidite compounds are disclosed. The phosphoramidites are useful, for example, for the preparation of oligonucleotides by solid state oligonucleotide synthetic regimes.

  揭示了改进的磷酰胺酰胺化合物制备方法。这些磷酰胺酰胺化合物可用于固相寡核苷酸合成方案的制备，例如。
• A multi-gram-scale stereoselective synthesis of Z-endoxifen
  作者：Lech-Gustav Milroy、Bartjan Koning、Daphne S.V. Scheppingen、Nynke G.L. Jager、Jos H. Beijnen、Jan Koek、Luc Brunsveld

  DOI：10.1016/j.bmcl.2018.03.008

  日期：2018.5

  endocrine therapy. Future pharmacological and pre-clinical studies of Z-endoxifen would benefit from reliable and efficient synthetic access to the drug. Here, we describe a short and efficient, stereoselective synthesis of Z-endoxifen capable of delivering multi-gram (37 g) quantities of the drug in >97% purity with a Z/E ratio >99% after trituration.

  Z- Endoxifen被广泛认为是他莫昔芬最活跃的代谢产物，最近在标准内分泌疗法失败后的转移性乳腺癌的I期临床试验中显示出26.3％的临床获益。Z-endoxifen的未来药理和临床前研究将受益于可靠有效的药物合成途径。在这里，我们描述了一种短而有效的，立体选择性的Z-内多昔芬合成方法，该方法能够在研磨后以> 97％的纯度提供多克（37 g）量的药物，Z / E比率> 99％。
• Gefitinib-Tamoxifen Hybrid Ligands as Potent Agents against Triple-Negative Breast Cancer
  作者：Carine M. Abdelmalek、Zexi Hu、Thales Kronenberger、Jenni Küblbeck、Franziska J. M. Kinnen、Salma S. Hesse、Afsin Malik、Mark Kudolo、Raimund Niess、Matthias Gehringer、Lars Zender、Paula A. Witt-Enderby、Darius P. Zlotos、Stefan A. Laufer

  DOI：10.1021/acs.jmedchem.1c01646

  日期：2022.3.24

  connecting tamoxifen or endoxifen with the EGFR-inhibitor gefitinib via a covalent linkage. These hybrid ligands retain both ER antagonist activity and EGFR inhibition. The most potent analogues exhibited single-digit nanomolar activities at both targets. The amide-linked endoxifen-gefitinib drug conjugates 17b and 17c demonstrated the most favorable anti-cancer profile in cellular viability assays on MCF7

  抗癌药物偶联物可能受益于同时作用于两个靶点，从而可能克服当前癌症治疗的缺点，例如疗效不足、毒性高和产生耐药性。与两种单靶点药物的组合相比，它们可能具有药代动力学简单和药物-药物相互作用较少的优势。在这里，我们报告了一系列通过共价键将他莫昔芬或安多昔芬与 EGFR 抑制剂吉非替尼连接起来的化合物。这些杂合配体保留了 ER 拮抗剂活性和 EGFR 抑制作用。最有效的类似物在两个目标上都表现出个位数的纳摩尔活性。酰胺连接的 endoxifen-gefitinib 药物偶联物17b和17c在 MCF7、MDA-MB-231、MDA-MB-468 和 BT-549 乳腺癌细胞的细胞活力测定中证明了最有利的抗癌谱。最重要的是，在 TNBC 细胞中，17b和17c显示出纳摩尔 IC 50值（380 nM – 970 nM），并且与它们的对照化合物及其组合相比，它们的抗癌活性更好。
• Azide-Free Synthesis of <i>N</i>-Alkyliminophosphoranes from Phosphines and Hydroxylamine Derivatives
  作者：Eric Falk、Allegra Franchino、Teresa Horak、Laura Gürtler、Bill Morandi

  DOI：10.1021/acs.orglett.3c00366

  日期：2023.3.17

  A broadly applicable and efficient method for the synthesis of N-alkyliminophosphoranes from phosphines that does not use potentially hazardous alkyl azides is reported. Under iron catalysis, a hydroxylamine-derived triflic acid salt oxidizes phosphines to a wide range of iminophosphorane triflic acid salts. Diphosphines afford phosphine-iminophosphoranes that can serve as ligands in transition metal

  报道了一种广泛适用且有效的从膦合成N-烷基亚氨基正膦的方法，该方法不使用具有潜在危险的烷基叠氮化物。在铁催化下，羟胺衍生的三氟甲磺酸盐将膦氧化为多种亚氨基正膦三氟甲磺酸盐。二膦提供可作为过渡金属络合物配体的膦-亚氨基正膦。开发的方法可用于混合二亚氨基正膦的合成和无痕施陶丁格连接。
• FLUORINATED ZWITTERIONIC POLYMERS AND METHODS OF USE
  申请人：[en]CORNELL UNIVERSITY

  公开号：WO2023249926A2

  公开（公告）日：2023-12-28

  Fluorinated monomer compositions having the formula: A-L-Z (1), wherein A is a polymerizable group (e.g., a vinyl group); L is a bond or linking portion; Z is a zwitterionic moiety or a zwitterionic precursor moiety containing a protecting group capable of deprotection to form a charged group; wherein at least one hydrogen atom in A, L, and/or Z in Formula (1) is substituted by a fluorinated hydrocarbon group, wherein the fluorinated hydrocarbon group contains 1-12 carbon atoms and precisely or at least one, two, three, four, five, or six fluorine atoms. Also described herein are fluorinated zwitterionic polymers derived from such monomers. Also described herein are mixed-charge zwitterionic polymers. Other aspects include methods for producing the monomers and polymers, bulk material (e.g., hydrogel or copolymer hybrid) compositions of any of the zwitterionic polymers described herein, fouling-resistant and/or fouling releasing surfaces and objects, and nanoparticles containing the polymer or bulk material.