2,2-dimethyl-2,3-dihydrobenzofuran-7-yl trifluoromethanesulfonate | 308110-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,2-dimethyl-2,3-dihydrobenzofuran-7-yl trifluoromethanesulfonate
• 英文别名: 2,2-Dimethyl-7-(trifluoromethylsulfonyloxy)-2,3-dihydrobenzofuran；(2,2-dimethyl-3H-1-benzofuran-7-yl) trifluoromethanesulfonate
• CAS: 308110-31-8
• 化学式: C₁₁H₁₁F₃O₄S
• 分子量: 296.267
• InChiKey: ZXZQADALRDJRJB-UHFFFAOYSA-N

物化性质

• 沸点：
  328.0±42.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-2,3-dihydrobenzofuran-7-yl trifluoromethanesulfonate 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 重铬酸吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 16.5h， 生成 2,2-二甲基-2,3-二羟基-1-苯并呋喃-7-甲醛
  参考文献：
  名称：

  New Diarylmethylpiperazines as Potent and Selective Nonpeptidic δ Opioid Receptor Agonists with Increased In Vitro Metabolic Stability

  摘要：

  Nonpeptide delta opioid agonists are analgesics with a potentially improved side-effect and abuse liability profile, compared to classical opioids. Andrews analysis of the NIH nonpeptide lead SNC-80 suggested the removal of substituents not predicted to contribute to binding. This approach led to a simplified lead, N,N-diethyl-4-[phenyl( 1-piperazinyl)methyl]benzamide (1), which retained potent binding affinity and selectivity to the human delta receptor (IC50 = 11 nM, mu/delta = 740, kappa/delta > 900) and potency as a full agonist (EC50 = 36 nM) but had a markedly reduced molecular weight, only one chiral center, and increased in vitro metabolic stability. From this lead, the key pharmacophore groups for delta receptor affinity and activation were more clearly defined by SAR and mutagenesis studies. Further structural modifications on the basis of 1 confirmed the importance of the N,N-diethylbenzamide group and the piperazine lower basic nitrogen for delta binding, in agreement with mutagenesis data. A number of piperazine N-alkyl substituents were tolerated. In contrast, modifications of the phenyl group led to the discovery of a series of diarylmethylpiperazines exemplified by N,N-diethyl-4-[1-piperazinyl(8-quinolinyl)- methyl]benzamide (56) which had an improved in vitro binding profile (IC50 = 0.5 nM, mu/delta = 1239, EC50 = 3.6 nM) and increased in vitro metabolic stability compared to SNC-80.

  DOI：

  10.1021/jm000228x
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 呋喃酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到2,2-dimethyl-2,3-dihydrobenzofuran-7-yl trifluoromethanesulfonate
  参考文献：
  名称：

  [EN] SMALL MOLECULE MODULATORS OF MHC-I
  [FR] MODULATEURS À PETITES MOLÉCULES DU CMH-1

  摘要：

  本公开的发明是能够治疗病毒感染的化合物的实施例。例如，这些化合物能够通过作为免疫调节剂来抑制病毒对主要组织相容性复合物I（MHC-I）的降调，从而治疗、治愈或根除病毒感染（例如HIV感染）。更具体地，本公开涉及在治疗感染病毒的患者中使用杂环芳基化合物或其盐或类似物。所公开的化合物可以单独使用或与其他药理活性剂联合使用，以治疗、治愈或根除病毒，特别是在患有持续潜伏病毒感染的患者中。在某些实施例中，所公开的化合物可以单独使用或与其他药理活性剂联合使用，促进潜伏细胞中病毒产生的重新激活和这些细胞的根除。

  公开号：

  WO2019213295A1

文献信息

• Novel compounds
  申请人：——

  公开号：US20030105110A1

  公开（公告）日：2003-06-05

  Compounds of general formula (I), wherein R 1 selected from phenyl, pyridinyl, thiophenyl, furanyl, imidazolyl, and triazolyl; where each R 1 phenyl ring and R 1 heteroaromatic ring may optionally and independently be further substituted by 1, 2 or 3 substituents selected from straight and branched C 1 -C 6 alkyl, NO 2 , CF 3 , C 1 -C 6 alkoxy, chloro, fluoro, bromo, and iodo.

  通式（I）的化合物，其中R1选自苯基、吡啶基、噻吩基、呋喃基、咪唑基和三唑基；其中每个R1苯环和R1杂环可能且独立地进一步被1、2或3个取自直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘的取代基所取代。
• An Improved Palladium-Catalyzed Conversion of Aryl and Vinyl Triflates to Bromides and Chlorides
  作者：Jun Pan、Xinyan Wang、Yong Zhang、Stephen L. Buchwald

  DOI：10.1021/ol202098h

  日期：2011.9.16

  A facile Pd-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) is described. This method allows convenient access to a variety of aryl, heteroaryl, and vinyl halides in good to excellent yields and with greatly simplified conditions relative to our previous report.

  描述了芳基和乙烯基三氟甲磺酸酯在 Pd 催化下轻松转化为芳基和乙烯基卤化物（溴化物和氯化物）。与我们之前的报告相比，该方法可以方便地获得各种芳基、杂芳基和乙烯基卤化物，产率良好至优异，并且条件大大简化。
• Dual Nickel-/Palladium-Catalyzed Reductive Cross-Coupling Reactions between Two Phenol Derivatives
  作者：Baojian Xiong、Yue Li、Yin Wei、Søren Kramer、Zhong Lian

  DOI：10.1021/acs.orglett.0c02165

  日期：2020.8.21

  Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance of phenols. Here, we report a dual nickel-/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60

  可以容易地衍生自苯酚的底物之间的交叉偶联由于苯酚的含量高而极具吸引力。在这里，我们报道了芳基甲苯磺酸盐和芳基三氟甲磺酸酯之间双重的镍/钯催化的还原交叉偶联。可以从一个容易获得的苯酚中仅一步之遥就获得两种底物。该反应具有宽泛的官能团耐受性和底物范围（> 60个实例）。此外，它显示出对空间效应的低敏感性，这是通过合成2,2'-二取代的联芳基和完全取代的芳基产物证明的。天然产品和药品中苯酚的广泛存在使简单的后期功能化成为可能，例如ezetimibe和酪氨酸。
• [EN] HETEROCYCLE CDK INHIBITORS AND THEIR USE THEREOF<br/>[FR] INHIBITEURS DE CDK À HÉTÉROCYCLE ET LEUR UTILISATION
  申请人：PRELUDE THERAPEUTICS INC

  公开号：WO2022035799A1

  公开（公告）日：2022-02-17

  The disclosure is directed to, in part, to heterocycle CDK inhibitors, pharmaceutical compositions comprising the same, as well as methods of their use and preparation.

  该披露涉及部分杂环CDK抑制剂，包括含有这些抑制剂的药物组合物，以及它们的使用和制备方法。
• Piperazinomethylbenzamides as delta-opioid receptor agonists
  申请人：AstraZeneca AB

  公开号：US06680318B2

  公开（公告）日：2004-01-20

  The present application is directed to compounds having the general formula: and to the use of these compounds in therapeutic methods.

  本申请涉及具有以下通式的化合物以及这些化合物在治疗方法中的使用。