2-甲基-4-(6-甲氧基萘-2-基)丁-3-炔-2-醇 | 129112-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲基-4-(6-甲氧基萘-2-基)丁-3-炔-2-醇
• 英文名称: 2-methyl-4-(6-methoxynaphthalen-2-yl)but-3-yn-2-ol
• 英文别名: 4-(6-methoxy-naphth-2-yl)-2-methylbut-3-yn-2-ol；4-(6-Methoxy-2-naphthyl)-2-methyl-3-butyn-2-ol；4-(6-methoxynaphthalen-2-yl)-2-methylbut-3-yn-2-ol
• CAS: 129112-99-8
• 化学式: C₁₆H₁₆O₂
• mdl: MFCD22687256
• 分子量: 240.302
• InChiKey: WQDNQQZNADORGF-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  401.5±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-4-(6-甲氧基萘-2-基)丁-3-炔-2-醇 在 四(三苯基膦)钯 氢氧化钾 、 sodium hydroxide 、 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 25.0~70.0 ℃ 、2.03 MPa 条件下， 反应 60.0h， 生成 去氢萘普生
  参考文献：
  名称：

  一种简便实用的 2-(6-Methoxy-2-naphthyl)propenoic 合成方法

  摘要：

  描述了一种合成 2-(6-甲氧基-2-萘基) 丙烯酸的简便实用的方法，该方法是抗炎剂萘普生的前体。该方法包括 (1) Pd 催化的 2-溴-6-甲氧基萘的乙炔化，(2) HX 区域选择性加成到三键，以及 (3) Pd 催化的所得乙烯基卤化物的羰基化，然后是 (4) 碱性水解。

  DOI：

  10.1246/bcsj.63.640
• 作为产物：
  描述：

  6-溴-2-萘酚 在 bis-triphenylphosphine-palladium(II) chloride 、 铜 、 potassium carbonate 作用下， 以 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-甲基-4-(6-甲氧基萘-2-基)丁-3-炔-2-醇
  参考文献：
  名称：

  Time-Dependent Solid-State Polymorphism of a Series of Donor–Acceptor Dyads

  摘要：

  In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized, and their packing in the solid state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A)packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single-crystal analysis and XRD patterns were used to create models, wherein a packing model for the other two dyads is proposed. Ourfindings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid state.

  DOI：

  10.1021/cg401522v

文献信息

• A Convenient Route to Condensed-Ring Aromatic Acetylenes
  作者：Geoffrey T. Crisp、Yu-Lin Jiang

  DOI：10.1080/00397919808004825

  日期：1998.7

  Abstract Palladium catalysed coupling of aryl halides with 3-methylbut-1-yn-3-ol and a subsequent base-induced retro-Favorsky reaction gave the corresponding ethynyl aromatics in good to excellent yields.

  摘要 钯催化芳基卤化物与 3-methylbut-1-yn-3-ol 偶联以及随后的碱诱导逆 Favorsky 反应得到相应的乙炔基芳烃，收率良好至极好。
• Asymmetric Intermolecular Heck Reaction of Propargylic Acetates and Cycloalkenes to Access Fused Cyclobutenes
  作者：Zhiwei Jiao、Qi Shi、Jianrong Steve Zhou

  DOI：10.1002/anie.201708435

  日期：2017.11.13

  An intermolecular Heck reaction between propargylic acetates and cyclic olefins results in the enantioselective synthesis of highly strained cyclobutenes.

  炔丙基乙酸酯和环状烯烃之间的分子间Heck反应导致高度应变的环丁烯的对映选择性合成。
• Substituted naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US20030018067A1

  公开（公告）日：2003-01-23

  This invention provides compounds which act as inhibitors of plasminogen activator inhibitor-1 (PAI-1) of the formula: 1 wherein: R, R 1 , R 2 , and R 3 are H, alkyl, cycloalkyl, —CH 2 -(cycloalkyl), alkanoyl, halo, hydroxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, perfluoroalkyl, alkoxy, amino, —NH(alkyl), —N(alkyl) 2 , or perfluoroalkoxy; R 4 is H, alkyl, perflouroalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkenyl, alkenyl-aryl, aryl, —CH 2 R 5 , —CH(OH)R 5 , —C(O)R 5 , —CH(SH)R 5 , or —C(S)R 5 ; R 5 is H, alkyl, perflouroalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkenyl, alkenyl-aryl; R 6 is H, alkyl, cycloalkyl, —CH 2 -cycloalkyl, alkylaryl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl; n is an integer of 0-6; A is COOH, or an acid mimic; or a pharmaceutically acceptable salt or ester form thereof, as well as pharmaceutical compositions and methods using these compounds to treat or prevent conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis.

  本发明提供了一种化合物，该化合物作为纤溶酶原激活物抑制剂-1（PAI-1）的抑制剂，其化学式为：1，其中：R、R1、R2和R3为H、烷基、环烷基、—CH2-（环烷基）、烷酰基、卤素、羟基、芳基、取代芳基、杂芳基、取代杂芳基、全氟烷基、烷氧基、氨基、—NH（烷基）、—N（烷基）2或全氟烷氧基；R4为H、烷基、全氟烷基、芳基、取代芳基、杂芳基、取代杂芳基、烯基、烯基-芳基、芳基、—CH2R5、—CH(OH)R5、—C(O)R5、—CH(SH)R5或—C(S)R5；R5为H、烷基、全氟烷基、芳基、取代芳基、杂芳基、取代杂芳基、烯基、烯基-芳基；R6为H、烷基、环烷基、—CH2-环烷基、烷基芳基、芳基、取代芳基、杂芳基或取代杂芳基；n为0至6的整数；A为COOH或酸类似物；或其药学上可接受的盐或酯形式，以及使用这些化合物治疗或预防由纤溶紊乱引起的疾病，如深静脉血栓和冠心病，以及肺纤维化的药物组合物和方法。
• [EN] NAPHTHYL BENZOFURAN DERIVATIVES AS INHIBITORS OF PLASMINOGEN ACTIVATOR INHIBITOR-1 (PAI-1)<br/>[FR] DERIVES DU NAPHTHYL BENZOFURANE INHIBITEURS DE L'INHIBITEUR 1 DE L'ACTIVATEUR DU PLASMINOGENE (PAI-1)
  申请人：WYETH CORP

  公开号：WO2003000671A1

  公开（公告）日：2003-01-03

  This invention provides compounds which act as inhibitors of plasminogen activator inhibitor-1 (PAI-1) of the formula (1), wherein: R, R1, R2, and R3 are H, alkyl, cycloalkyl, -CH2-(cycloalkyl), alkanoyl, halo, hydroxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, perfluoroalkyl, alkoxy, amino, -NH(alkyl), -N(alkyl)2, or perfluoroalkoxy; R4 is H, alkyl, perflouroalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkenyl, alkenyl-aryl, aryl, -CH2R5, -CH(OH)R5, -C(O)R5, -CH(SH)R5, or -G(S)R5; R5 is H, alkyl, perflouroalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkenyl, alkenyl-aryl; R6 is H, alkyl, cycloalkyl, -CH2-cycloalkyl, alkylaryl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl; n is an integer of 0-6; A is COOH, or an acid mimic; or a pharmaceutically acceptable salt or ester form thereof, as well as pharmaceutical compositions and methods using these compounds to treat or prevent conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis, and processes for the preparation of such compounds.

  本发明提供了一种公式（1）的纤溶酶原激活抑制剂-1（PAI-1）抑制剂化合物，其中：R、R1、R2和R3是H、烷基、环烷基、-CH2-（环烷基）、烷酰基、卤素、羟基、芳基、取代芳基、杂环芳基、取代杂环芳基、全氟烷基、烷氧基、氨基、-NH（烷基）、-N（烷基）2或全氟烷氧基；R4是H、烷基、全氟烷基、芳基、取代芳基、杂环芳基、取代杂环芳基、烯基、烯基-芳基、芳基、-CH2R5、-CH（OH）R5、-C（O）R5、-CH（SH）R5或-G（S）R5；R5是H、烷基、全氟烷基、芳基、取代芳基、杂环芳基、取代杂环芳基、烯基、烯基-芳基；R6是H、烷基、环烷基、-CH2-环烷基、烷基芳基、芳基、取代芳基、杂环芳基或取代杂环芳基；n是0-6的整数；A是COOH或酸类模拟物；或其药学上可接受的盐或酯形式，以及使用这些化合物治疗或预防由纤溶障碍引起的疾病的制药组合物和方法，例如深静脉血栓和冠心病，以及肺纤维化，并且制备这些化合物的方法。
• Rhodium-Catalyzed Coordination-Assisted Regioselective and Migratory Three-Point Double Annulation of <i>o</i>-Alkenyl Phenols with Tertiary Propargyl Alcohols
  作者：Attunuri Nagireddy、Ramesh Kotipalli、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.2c01819

  日期：2022.7.22

  disclose herein a Rh(III)-catalyzed migratory three-point double annulation of o-alkenyl phenols with propargyl alcohols for de novo construction of naphtho furan derivatives in a regio- and chemoselective manner. The protocol orchestrates two new rings with four new bonds in one operation without the need for any additive. Necessary labeled and control experiments are conducted to elucidate the reaction

  我们在此公开了 Rh(III) 催化的邻烯基酚与炔丙醇的迁移三点双环化，用于以区域选择性和化学选择性的方式从头构建萘并呋喃衍生物。该协议在一次操作中编排了两个新环和四个新键，而无需任何添加剂。进行必要的标记和对照实验以阐明反应机理。除了形成额外的（呋喃）环外，叔羟基被发现对于通过与铑螯合以形成关键的螺环中间体来控制炔烃的区域选择性插入以及通过不寻常和选择性的烯烃重排来强制扩环都是至关重要的。该协议具有可扩展性，并显示出对天然产物后期功能化的耐受性。