17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl trifluoromethanesulfonate | 205375-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl trifluoromethanesulfonate
• 英文别名: (5a)-17-(Cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl trifluoromethanesulfonate；[(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] trifluoromethanesulfonate
• CAS: 205375-23-1
• 化学式: C₂₁H₂₂F₃NO₆S
• 分子量: 473.47
• InChiKey: QSPGSENWVSPIQZ-XFWGSAIBSA-N

物化性质

• 沸点：
  593.5±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 甲酸 、 三正丁胺 、 1,3-双(二苯基膦)丙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以68%的产率得到3-desoxynaltrexone
  参考文献：
  名称：

  3-取代的3-脱氧萘并吲哚衍生物的合成和生物活性。

  摘要：

  使用钯催化的转化合成了纳曲多（NTI）的3-个未取代和取代的类似物，并确定了它们与阿片受体的结合亲和力。尽管3-脱氧类似物显示出与NTI相当的δ选择性，但是所有新化合物对δ受体具有低亲和力，表明NTI的3-氧原子对于与δ-阿片样物质受体相互作用具有重要作用。

  DOI：

  10.1016/s0960-894x(98)00105-x
• 作为产物：
  描述：

  纳曲酮 生成 17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2001, 11, 1717-1721

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR FORMING A CARBON-CARBON BOND<br/>[FR] PROCÉDÉ DE FORMATION D'UNE LIAISON CARBONE-CARBONE
  申请人：UNIV MANCHESTER

  公开号：WO2019215426A1

  公开（公告）日：2019-11-14

  A process for forming a carbon-carbon bond to couple an aryl or heteroaryl group of a first compound with an aryl or heteroaryl group of a second compound, the process comprising reacting the first compound with the second compound in the presence of a catalytically effective amount of a neutral or cationic ruthenium(II) catalyst of formula (I):

  一种形成碳-碳键的工艺，用于将第一化合物中的芳基或杂芳基团与第二化合物中的芳基或杂芳基团偶联，该工艺包括在存在公式(I)的中性或阳离子钌(II)催化剂的催化有效量下，使第一化合物与第二化合物反应：
• 3-Carboxamido analogues of morphine and naltrexone
  作者：Mark P. Wentland、Rongliang Lou、Christoph M. Dehnhardt、Wenhu Duan、Dana J. Cohen、Jean M. Bidlack

  DOI：10.1016/s0960-894x(01)00278-5

  日期：2001.7

  In response to the unexpectedly high affinity for opioid receptors observed in a novel series of cyclazocine analogues where the prototypic 8-OH was replaced by a carboxamido group, we have prepared the corresponding 3-CONH(2) analogues of morphine and naltrexone. High affinity (K(i)=34 and 1.7nM) for mu opioid receptors was seen, however, the new targets were 39- and 11-fold less potent than morphine

  为了响应在一系列新的环偶氮类似物中观察到的对阿片样物质受体的意外高亲和力，其中原型8-OH被羧酰胺基团取代，我们制备了吗啡和纳曲酮的相应3-CONH（2）类似物。观察到对μ阿片样物质受体具有高亲和力（K（i）= 34和1.7nM），但是，新靶标的效力分别比吗啡和纳曲酮低39倍和11倍。
• Cyclometallated ruthenium catalyst enables late-stage directed arylation of pharmaceuticals
  作者：Marco Simonetti、Diego M. Cannas、Xavier Just-Baringo、Iñigo J. Vitorica-Yrezabal、Igor Larrosa

  DOI：10.1038/s41557-018-0062-3

  日期：2018.7

  Biaryls are ubiquitous core structures in drugs, agrochemicals and organic materials that have profoundly improved many aspects of our society. Although traditional cross-couplings have made practical the synthesis of many biaryls, C–H arylation represents a more attractive and cost-effective strategy for building these structural motifs. Furthermore, the ability to install biaryl units in complex molecules via late-stage C–H arylation would allow access to valuable structural diversity, novel chemical space and intellectual property in only one step. However, known C–H arylation protocols are not suitable for substrates decorated with polar and delicate functionalities, which are commonly found in molecules that possess biological activity. Here we introduce a class of ruthenium catalysts that display a unique efficacy towards late-stage arylation of heavily functionalized substrates. The design and development of this class of catalysts was enabled by a mechanistic breakthrough on the Ru(ii)-catalysed C–H arylation of N–chelating substrates with aryl (pseudo)halides, which has remained poorly understood for nearly two decades. Nearly two decades after its discovery, the Ru(II)-catalysed C–H arylation of N-chelating aromatics with aryl halides was reinvestigated and a new key reaction intermediate was uncovered. A thorough mechanistic elucidation has now led to the development of a new class of catalysts with unique efficacy towards late-stage arylation of ‘real-world’ compounds.

  双芳烃是药物、农用化学品和有机材料中普遍存在的核心结构，对我们社会的许多方面产生了深远的影响。尽管传统的交叉偶联反应使得合成许多双芳烃成为可能，但C–H芳构化反应则是一种更具吸引力和成本效益的构建这些结构单元的策略。此外，通过后期C–H芳构化在复杂分子中引入双芳烃单元，将使我们能够仅用一步访问有价值的结构多样性、新的化学空间和知识产权。然而，已知的C–H芳构化方法并不适用于装饰有极性和精细官能团的底物，而这类官能团通常存在于具生物活性的分子中。在这里，我们介绍一类展现出对重官能化底物的后期芳构化反应具有独特效能的钌催化剂。该类催化剂的设计和开发得益于对钌（II）催化的N-螯合底物与芳香（伪）卤化物之间的C–H芳构化反应的机制突破，这一反应在近二十年来一直未得到充分理解。在其发现近二十年后，N-螯合芳烃与芳香卤化物的Ru(II)催化C–H芳构化反应进行了再研究，并揭示了一个新的关键反应中间体。经过彻底的机制阐明，我们现在成功开发出一类对“现实世界”化合物的后期芳构化具有独特效能的新型催化剂。
• [EN] QUATERNARY OPIOID CARBOXAMIDES<br/>[FR] CARBOXAMIDES OPIOÏDES QUATERNAIRES
  申请人：RENSSELAER POLYTECH INST

  公开号：WO2009023567A1

  公开（公告）日：2009-02-19

  Compounds of formulas (A) and (B) are disclosed. The compounds of this invention are useful for ameliorating the side effects of therapeutic opiates.

  本发明揭示了化合物(A)和(B)的配方。本发明的化合物对于缓解治疗阿片类药物的副作用很有用。
• Quaternary opioid carboxamides
  申请人：Rensselaer Polytechnic Institute

  公开号：US08263807B2

  公开（公告）日：2012-09-11

  Compounds of formulas: are disclosed. The compounds are useful for ameliorating the side effects of therapeutic opiates.

  公式为的化合物被披露。这些化合物对于改善治疗鸦片副作用是有用的。