5-溴萘-2-甲醛 | 122349-66-0

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-溴萘-2-甲醛
• 英文名称: 5-bromonaphthalene-2-carbaldehyde
• 英文别名: 5-bromo-2-naphthaldehyde；5-bromonaphthalene-2-formaldehyde
• CAS: 122349-66-0
• 化学式: C₁₁H₇BrO
• 分子量: 235.08
• InChiKey: OQAFFLFJQFWYHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-溴萘-2-甲醛 在 三乙基硅烷 、 乙基溴化镁 、 氢溴酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-[(5-bromo-2-naphthyl)methyl]-5-(4-piperidyl)-3-isoxazolol hydrobromide
  参考文献：
  名称：

  Potent 4-Aryl- or 4-Arylalkyl-Substituted 3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Molecular Modeling

  摘要：

  We have previously described a series of competitive GABA(A) antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3-isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5-(4-piperidyl)-3-isoxazolol (5), provided affinity for the GABA(A) receptor site higher than that of the standard GABA(A) receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring, Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (7l-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABA(A) receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (K-i = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds. 6,e-k. with retained high affinity for the GABA(A) receptor (K-i = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons. all of the tested compounds were able to inhibit the effect of the Specific GABA(A) agonist, isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that, of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.

  DOI：

  10.1021/jm049256w
• 作为产物：
  描述：

  5-bromo-2-naphthalenylmethyl bromide 在 2-硝基丙烷 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 65.0h， 以81%的产率得到5-溴萘-2-甲醛
  参考文献：
  名称：

  Potent 4-Aryl- or 4-Arylalkyl-Substituted 3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Molecular Modeling

  摘要：

  We have previously described a series of competitive GABA(A) antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3-isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5-(4-piperidyl)-3-isoxazolol (5), provided affinity for the GABA(A) receptor site higher than that of the standard GABA(A) receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring, Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (7l-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABA(A) receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (K-i = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds. 6,e-k. with retained high affinity for the GABA(A) receptor (K-i = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons. all of the tested compounds were able to inhibit the effect of the Specific GABA(A) agonist, isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that, of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.

  DOI：

  10.1021/jm049256w

文献信息

• [EN] 15-PGDH INHIBITORS<br/>[FR] INHIBITEURS DE 15-PGDH
  申请人：KYORIN SEIYAKU KK

  公开号：WO2020160151A1

  公开（公告）日：2020-08-06

  A compound having one of formula (1), formula (2), formula (3) and formula (4) or a pharmacologically acceptable salt thereof.

  具有以下式之一的化合物（1），（2），（3）和（4）或其药理学上可接受的盐。
• 균열 검출장치
  申请人：HYUNDAI MIPO DOCKYARD CO., LTD. 주식회사 현대미포조선(119987029839) Corp. No ▼ 181211-0000526

  公开号：KR20160001537U

  公开（公告）日：2016-05-11

  본 고안에 따른 균열 검출장치는, 부분 또는 전체가 상기 파이프의 단부에 내삽되도록 설치되고, 외주면 둘레가 가변하는 고무튜브를 포함하는 원통형의 실링지그; 상기 실링지그의 전방에 설치되어, 상기 파이프의 내부에 물을 분사하는 분사부; 상기 실링지그의 후방에 설치되며, 상기 분사부와 연통하도록 설치되는 연결관; 상기 연결관으로 물을 공급하는 급수부; 및 상기 연결관의 후단에 물의 분사방향과 수직방향으로 연장되어, 후면이 지지대상물에 접하도록 설치되는 받침부를 포함한다. 이러한 본 고안에 따른 균열 검출장치는, 상기 고무튜브의 외주 둘레가 필요에 따라 가변하여, 상기 파이프의 단부를 보다 견고하게 밀폐시킬 수 있다. 또한 물을 분사하는 힘에 대향하여 받침부를 설치함으로써, 실링지그의 밀림현상을 방지할 수 있다.

  根据本设计的裂缝检测装置，部分或整个安装在管道端部内插，包括一个圆柱形密封夹具，其周围包括可变外周的橡胶管；安装在密封夹具前方，在管道内部喷水的喷射部；安装在密封夹具后方，与喷射部相连通的连接管；通过连接管供水的供水部；以及延伸到连接管后端，与水的喷射方向和垂直方向相交，安装在支撑物上以接触后面的支撑部。根据本设计的裂缝检测装置，橡胶管的外周根据需要可变化，可以更牢固地密封管道端部。此外，通过安装支撑部以抵抗喷水力，可以防止密封夹具的移位现象。
• Pesticides
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0143593A2

  公开（公告）日：1985-06-05

  A compound of Formula I: Formula I wherein: Ar represents a polynuclear carboxylic or heterocyclic fused ring system having at least one carbocyclic or heterocyclic ring of aromatic character, the polynuclear ring system optionally carrying one or more of the substituents halogen, C1-C8 alkyl -CF3, or -OCFyH3-y, wherein y is 0-3; n is 0 or 1 and m is 1 -11 Z represents a group of Formula: wherein: RA and RB which may be identical or different each represent hydrogen or methyl; Rc represents methyl; Ro represents methyl, ethyl, n-propyl, isopropyl, t-butyl, or vinyl; and RE represents hydrogen or methyl or wherein: Rc and RD together with Cβ form a cyclopropane or a cyclobutane ring or together form a methylene group (=CH2) or wherein: RA and RB together with Cα and Cβ form a cyclobutane ring.

  式 I 的化合物：式 I 其中 Ar 代表多核羧基或杂环融合环体系，该多核环体系具有至少一个芳香性质的碳环或杂环，该多核环体系可选带一个或多个取代基卤素、C1-C8 烷基 -CF3 或 -OCFyH3-y，其中 y 为 0-3； n 为 0 或 1，m 为 1-11 Z 代表式中的一个基团： 其中 RA 和 RB 可以相同或不同，各自代表氢或甲基； Rc 代表甲基 Ro 代表甲基、乙基、正丙基、异丙基、叔丁基或乙烯基；以及 RE 代表氢或甲基 或 其中 Rc 和 RD 与 Cβ 一起形成环丙烷环或环丁烷环，或一起形成亚甲基 (=CH2) 或 RA 和 RB 与 Cα 和 Cβ 一起形成环丁烷环。
• Helicene Aromaticity Deviates from the Clar Rule—On the Electronic Dissimilarity of Large Isomeric Fibonacenes
  作者：Ludmilla Sturm、Albert Artigas、Yoann Coquerel、Ivan H. Bechtold、Fabien Durola、Harald Bock

  DOI：10.1002/anie.202403170

  日期：——

  Long isomeric fibonacenes—a phenacene, a helicene and a croissant-shaped isomer—are found to show strikingly different absorption and emission spectra, despite their equivalent Kekulé structures. Complementary computations based either on magnetic or electronic criteria for aromaticity indicate that in long helicenes, the Clar and Kekulé rules of preferred sextet localization do not hold.

  长异构体斐波那苯——非并苯、螺旋烯和羊角面包形异构体——被发现表现出截然不同的吸收和发射光谱，尽管它们具有相同的凯库勒结构。基于芳香性的磁性或电子标准的互补计算表明，在长螺旋烯中，首选六重奏定位的克拉和凯库勒规则不成立。
• 具有大体积炔基侧基的二胺单体、聚苯并噁唑前体、感光性树脂组合物及其应用
  申请人：波米科技有限公司

  公开号：CN115974762A

  公开（公告）日：2023-04-18

  本发明公开了一种具有大体积炔基侧基的二胺单体、聚苯并噁唑前体、感光性树脂组合物及其应用，该二胺单体中同时含有邻羟基苯胺基团和芳香型大体积炔基侧基，可以用于制备具有大体积炔基侧基的聚苯并噁唑前体树脂，进而可以制备正型感光性树脂组合物，该正型感光性树脂组合物显影时对比度优异；此外，由此感光性树脂组合物可制备聚苯并噁唑固化膜，由于二胺单体向树脂中引入了芳香型大体积炔基侧基，从而可以有效降低固化膜介电常数，炔基的交联同时可以改善固化膜的成膜性，提高其耐溶剂性和耐热性。