6-溴-1-甲基萘-2-醇 | 16667-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-溴-1-甲基萘-2-醇
• 英文名称: 6-bromo-1-methylnaphthalen-2-ol
• 英文别名: 6-bromo-1-methyl-2-naphthol；2-Naphthol, 6-bromo-1-methyl-
• CAS: 16667-01-9
• 化学式: C₁₁H₉BrO
• 分子量: 237.096
• InChiKey: YNZVWWALVATSDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-溴-1-甲基萘-2-醇 在 吡啶 、 咪唑 、 1,1'-双(二苯基膦)二茂铁 、 正丁基锂 、 四丁基氟化铵 、 palladium diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， -70.0~70.0 ℃ 、101.33 kPa 条件下， 反应 19.16h， 生成 methyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-1-methyl-2-naphthoate
  参考文献：
  名称：

  17,20-Lyase inhibitors. Part 4: Design, synthesis and structure–activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors

  摘要：

  A novel series of naphthylmethylimidazole derivatives and related compounds have been investigated as selective 17,20-lyase inhibitors. Optimization of the substituent at the 6-position on the naphthalene ring was performed to yield a methylcarbamoyl derivative, which exhibited potent inhibitory activity against human 17,20-lyase and promising selectivity (> 200-fold) for 17,20-lyase over CYP3A4. Further modifications of the methylcarbamoyl derivative led to the discovery of the corresponding tricyclic compound, which showed highly potent activity against human 17,20-lyase (IC50 19 nM) and good selectivity (> 1000-fold) for inhibition of 17,20-lyase over CYP3A4. Additional biological evaluation revealed that the tricyclic compound had potent in vivo efficacy in monkeys and favorable pharmacokinetic profiles when administered in rats. Asymmetric synthesis of the selective tricyclic inhibitor was also achieved using a chiral alpha-hydroxy ketone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.017
• 作为产物：
  描述：

  N-(6-bromo-1-methyl-2-oxo-1,2-dihydro-[1]naphthyl)-N-phenyl-acetamide 在 溶剂黄146 、 锌 作用下， 生成 6-溴-1-甲基萘-2-醇
  参考文献：
  名称：

  Fries; Kuester, Justus Liebigs Annalen der Chemie, 1929, vol. 470, p. 36

  摘要：

  DOI：

文献信息

• Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone
  作者：Muhammet Uyanik、Naoto Sahara、Kazuaki Ishihara

  DOI：10.1002/ejoc.201801063

  日期：2019.1.10

  A practical and efficient chlorination of naphthols and phenols was developed using transient chlorinating species generated in situ from inexpensive sodium chloride and Oxone as a Cl source and oxidant, respectively, under mild conditions.

  利用温和条件下从廉价的氯化钠和Oxone分别作为Cl源和氧化剂原位生成的瞬时氯化物，开发了一种实用而有效的氯化萘和苯酚的方法。
• Naphthalene derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06573289B1

  公开（公告）日：2003-06-03

  A composition containing a compound of the formula: wherein A is a nitrogen-containing heterocyclic group which may be substituted, R1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R2 is a hydrogen atom or a lower alkyl group which may be substituted, R3, R4, R5, R6, R7, R8 and R9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  包含以下公式化合物的组合物： 其中A是可被取代的含氮杂环基团，R1是氢原子、可被取代的烃基团或可被取代的单环芳族杂环基团，R2是氢原子或可被取代的低级烷基团，R3、R4、R5、R6、R7、R8和R9独立地是氢原子、可被取代的烃基团、可被取代的羟基、可被取代的硫醇基、可被取代的氨基、酰基或卤素原子，其盐或前药对类固醇C17,20-裂解酶具有抑制作用，并且对于例如预防治疗原发恶性肿瘤、其转移和复发等是有用的。
• 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。
• Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters
  作者：Alemayehu Gashaw Woldegiorgis、Zhao Han、Xufeng Lin

  DOI：10.1021/acs.orglett.1c01849

  日期：2021.9.3

  γ-alkynyl-α-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and efficient access to asymmetric construction of a broad range of axially chiral allene-derived naphthalenones bearing quaternary stereocenters in good yields with high diastereoselectivities and enantioselectivities.

  通过手性磷酸催化，公开了具有完全原子经济性的 1-取代 2-萘酚和 β,γ-炔基-α-亚氨基酯的高度区域选择性、非对映选择性和对映选择性脱芳构化反应。该协议提供了对广泛的轴向手性丙二烯衍生的萘酮的不对称构建的方便和有效的访问，这些萘酮具有良好的收率，具有高非对映选择性和对映选择性。
• [EN] (PIPERIDIN-3-YL)(NAPHTHALEN-2-YL)METHANONE DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE HISTONE DEMETHYLASE KDM2B FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE (PIPÉRIDIN-3-YL)(NAPHTALÉN-2-YL)MÉTHANONE ET COMPOSÉS ASSOCIÉS UTILISÉS COMME INHIBITEURS DE L'HISTONE DÉMÉTHYLASE KDM2B POUR LE TRAITEMENT DU CANCER
  申请人：GENENTECH INC

  公开号：WO2016112284A1

  公开（公告）日：2016-07-14

  The present invention relates to (piperidin-3-yl)(naphthalen-2-yl) methanone derivatives and related compounds as inhibitors of one or more histone demethylses, such as KDM2b. The invention also provides pharmaceutically acceptable compositions comprising compounds of the present invention and discloses methods of using said compositions in the treatment of cancer, such as lung cancer, leukemia or lymphoma.

  本发明涉及（哌啶-3-基）（萘-2-基）甲酮衍生物和相关化合物，作为一种或多种组蛋白去甲基酶抑制剂，如KDM2b。该发明还提供了包括本发明化合物的药学上可接受的组合物，并公开了使用该类组合物治疗癌症，如肺癌、白血病或淋巴瘤的方法。