O-(2-trifluoromethylphenyl)hydroxylamine | 160725-42-8

• 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: O-(2-trifluoromethylphenyl)hydroxylamine
• 英文别名: O-[2-(trifluoromethyl)phenyl]hydroxylamine
• CAS: 160725-42-8
• 化学式: C₇H₆F₃NO
• mdl: MFCD09029770
• 分子量: 177.126
• InChiKey: TVLXOGBRADDHAM-UHFFFAOYSA-N

物化性质

• 沸点：
  208.3±40.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-(2-trifluoromethylphenyl)hydroxylamine 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 作用下， 以 乙醚 为溶剂， 反应 3.08h， 生成 2-(1-methoxyethyl)-6-(trifluoromethyl)phenol
  参考文献：
  名称：

  用于监测活细胞和植物中乙烯的基于活性的传感荧光探针

  摘要：

  乙烯（ET）是一种重要的气态植物激素。非常需要开发用于监测活细胞中乙烯的荧光探针。我们报告了在醇的存在下，N-苯氧基乙酰胺与乙烯的高效 Rh III催化偶联。新发现的偶联反应表现出广泛的N-苯氧基乙酰胺和优异的区域选择性。我们使用该策略成功开发了三种荧光标记的基于Rh III的荧光香豆素-乙烯探针 ( CEP )，用于选择性和定量检测乙烯。CEP-1表现出最高的灵敏度，空气中乙烯的检测限为 52 ppb。此外，CEP-1已成功应用于活 CHO-K1 细胞的成像以及监测烟草和拟南芥植物中乙烯生物合成的内源性诱导变化。这些结果表明，CEP-1在阐明生物系统中乙烯生物合成和乙烯信号转导的时空调控方面具有巨大潜力。

  DOI：

  10.1002/anie.202108335
• 作为产物：
  描述：

  ethyl N-(2-trifluoromethylphenoxy)acetimidate 在 高氯酸 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 O-(2-trifluoromethylphenyl)hydroxylamine
  参考文献：
  名称：

  Inhibitors of transthyretin amyloid fibril formation

  摘要：

  Bisaryloxime醚和bisarylhydroazones被证明对抑制甲状腺前蛋白淀粉样纤维的形成有效。

  公开号：

  US20060178527A1

文献信息

• Fluorous Tagged <i>N</i>-Hydroxy Phthalimide for the Parallel Synthesis of <i>O</i>-Aryloxyamines
  作者：Florence S. Gaucher-Wieczorek、Ludovic T. Maillard、Bernard Badet、Philippe Durand

  DOI：10.1021/cc100098v

  日期：2010.9.13

  The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi’s method. A library of O-aryloxyamines

  在药物化学和基于片段的方法领域中，O-芳氧基胺的平行合成仍未满足。为了填补这一空白，采用了一种溶液阶段两步法，该方法基于（1）铜催化的芳基硼酸与带有氟标记的N-羟基邻苯二甲酰亚胺的交叉偶联，以及（2）使用Taguchi方法设计并优化了负载型氨解反应。以高产率，高纯度和多样性合成了O-芳氧基胺的文库。
• Inhibitors of Transthyretin Amyloid Fibril Formation
  申请人：Kelly Jeffery W.

  公开号：US20090054629A1

  公开（公告）日：2009-02-26

  Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.

  Bisaryloxime醚和bisarylhydroazones已被证明对抑制转甲状腺原蛋白淀粉样纤维的形成具有有效性。
• METHOD FOR PREPARING 3'-O-AMINO-2'-DEOXYRIBONUCLEOSIDE-5'-TRIPHOSPHATES
  申请人：DNA Script

  公开号：US20210300961A1

  公开（公告）日：2021-09-30

  Methods for preparing 3′-O-amino-2′-deoxyribonucleoside-5′-triphosphates with reduced 3′-hydroxy-2′-deoxyribonucleoside-5′-triphosphate contamination by converting 3′-(N-acetone-oxime)-2′-deoxynucleoside triphosphate to 3′-O-amine-2′-deoxynucleoside triphosphate by treatment with an aryl-oxyamine and compositions produced therefrom.

  制备方法，用于制备含有较少3'-羟基-2'-脱氧核苷酸-5'-三磷酸污染的3'-O-氨基-2'-脱氧核苷酸-5'-三磷酸，通过将3'-(N-丙酮肟)-2'-脱氧核苷酸三磷酸转化为3'-O-氨基-2'-脱氧核苷酸三磷酸，并由此产生的组合物。
• Bisaryloxime Ethers as Potent Inhibitors of Transthyretin Amyloid Fibril Formation
  作者：Steven M. Johnson、H. Michael Petrassi、Satheesh K. Palaninathan、Nilofar N. Mohamedmohaideen、Hans E. Purkey、Christopher Nichols、Kyle P. Chiang、Traci Walkup、James C. Sacchettini、K. Barry Sharpless、Jeffery W. Kelly

  DOI：10.1021/jm049274d

  日期：2005.3.1

  Amyloid fibril formation by the plasma protein transthyretin (TTR), requiring rate-limiting tetramer dissociation and monomer misfolding, is implicated in several human diseases. Amyloidogenesis can be inhibited through native state stabilization, mediated by small molecule binding to TTR's primarily unoccupied thyroid hormone binding sites. New native state stabilizers have been discovered herein by the facile condensation of arylaldehydes with aryloxyamines affording a bisarylaldoxime ether library. Of the library's 95 compounds, 31 were active inhibitors of TTR amyloid formation in vitro. The bisaryloxime ethers selectively stabilize the native tetrameric state of TTR over the dissociative transition state under amyloidogenic conditions, leading to an increase in the dissociation activation barrier. Several bisaryloxime ethers bind selectively to TTR in human blood plasma over the plethora of other plasma proteins, a necessary attribute for efficacy in vivo. While bisarylaldoxime ethers are susceptible to degradation by N-O bond cleavage, this process is slowed by their binding to TTR. Furthermore, the degradation rate of many of the bisarylaldoxime ethers is slow relative to the half-life of plasma TTR. The bisaryloxime ether library provides valuable structure-activity relationship insight for the development of structurally analogous inhibitors with superior stability profiles, should that prove necessary.
• Synthesis and opioid activities of some naltrexone oxime ethers
  作者：BJ Mavunkel、WJ Rzeszotarski、PV Kaplita、DL DeHaven-Hudkins

  DOI：10.1016/0223-5234(94)90027-2

  日期：1994.1

  A series of alkyl, cycloalkyl, aryl, and aralkyl ethers of naltrexone oxime was prepared. The compounds were examined in binding assays for mu, delta and kappa opioid receptor affinity. In addition, the naltrexone oxime ethers were studied in animal models that measure opioid agonist and antagonist activity. These studies led to the discovery of several compounds, notably phenethyl 3e and phenylpropyl 3f ethers of naltrexone, which have a 10-fold increase in potency at the kappa opioid receptor with potent mu and kappa agonist properties in vivo.