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1-(9-溴菲-3-基)乙酮 | 6328-08-1

中文名称
1-(9-溴菲-3-基)乙酮
中文别名
——
英文名称
3-Acetyl-9-brom-phenanthren
英文别名
3-Acetyl-9-bromophenanthrene;1-(9-bromophenanthren-3-yl)ethanone
1-(9-溴菲-3-基)乙酮化学式
CAS
6328-08-1
化学式
C16H11BrO
mdl
——
分子量
299.167
InChiKey
PODNEAAXQLNICQ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.8
  • 重原子数:
    18
  • 可旋转键数:
    1
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.06
  • 拓扑面积:
    17.1
  • 氢给体数:
    0
  • 氢受体数:
    1

安全信息

  • 海关编码:
    2914700090

SDS

SDS:ffa2070e4a069f3193bde4a514cfec1a
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    1-(9-溴菲-3-基)乙酮 、 sodium hydroxide 、 盐酸 作用下, 以 1,4-二氧六环 为溶剂, 反应 1.0h, 以85%的产率得到9-bromophenanthrene-3-carboxylic acid
    参考文献:
    名称:
    Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors
    摘要:
    Competitive N-methyl-D-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N-1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives also display subtype selectivity among the more distantly related kainate receptor family. Compounds 18i and (-)-4 were the most potent kainate receptor antagonists, and 18i was selective for GluK1 versus GluK2, GluK3 and AMPA receptors. Modeling studies revealed structural features required for activity at GluK1 subunits and suggested that S674 was vital for antagonist activity. Consistent with this hypothesis, replacing the equivalent residue in GluK3 (alanine) with a serine imparts 18i antagonist activity. Antagonists with dual GluN2D and GluK1 antagonist activity may have beneficial effects in various neurological disorders. Consistent with this idea, antagonist 18i (30 mg/kg ip) showed antinociceptive effects in an animal model of mild nerve injury.
    DOI:
    10.1021/jm201230z
  • 作为产物:
    描述:
    9-溴菲乙酰氯 在 aluminum (III) chloride 作用下, 生成 1-(9-溴菲-3-基)乙酮
    参考文献:
    名称:
    Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors
    摘要:
    Competitive N-methyl-D-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N-1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives also display subtype selectivity among the more distantly related kainate receptor family. Compounds 18i and (-)-4 were the most potent kainate receptor antagonists, and 18i was selective for GluK1 versus GluK2, GluK3 and AMPA receptors. Modeling studies revealed structural features required for activity at GluK1 subunits and suggested that S674 was vital for antagonist activity. Consistent with this hypothesis, replacing the equivalent residue in GluK3 (alanine) with a serine imparts 18i antagonist activity. Antagonists with dual GluN2D and GluK1 antagonist activity may have beneficial effects in various neurological disorders. Consistent with this idea, antagonist 18i (30 mg/kg ip) showed antinociceptive effects in an animal model of mild nerve injury.
    DOI:
    10.1021/jm201230z
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文献信息

  • Synthesis of a Series of Novel 3,9-Disubstituted Phenanthrenes as Analogues of Known N-Methyl-d-aspartate Receptor Allosteric Modulators
    作者:Mark Irvine、Guangyu Fang、Richard Eaves、Maria Mayo-Martin、Erica Burnell、Blaise Costa、Georgia Culley、Arturas Volianskis、Graham Collingridge、Daniel Monaghan、David Jane
    DOI:10.1055/s-0034-1380114
    日期:2015.6

    9-Substituted phenanthrene-3-carboxylic acids have been reported to have allosteric modulatory activity at the N-methyl-d-aspartate (NMDA) receptor. This receptor is activated by the excitatory neurotransmitter l-glutamate and has been implicated in a range of neurological disorders such as schizophrenia, epilepsy and chronic pain, and in neurodegenerative disorders such as Alzheimer’s disease. Herein, the convenient synthesis of a wide range of novel 3,9-disubstituted phenanthrene derivatives starting from a few common intermediates is described. These new phenanthrene derivatives will help to clarify the structural requirements for allosteric modulation of the NMDA receptor.

    9-取代菲3-羧酸据报道具有对N-甲基-d-天冬氨酸(NMDA)受体的变构调节活性。该受体被兴奋性神经递质l-谷氨酸激活,并已被认为与一系列神经系统疾病(如精神分裂症、癫痫和慢性疼痛)以及神经退行性疾病(如阿尔茨海默病)有关。本文描述了从几种常见中间体出发合成一系列新型3,9-二取代菲衍生物的便捷方法。这些新的菲衍生物将有助于阐明对NMDA受体的变构调节的结构要求。
  • ALIPHATIC CHEMISTRY OF FLUORENE: PART III. SOME DERIVATIVES OF FLUORENE AND PHENANTHRENE
    作者:P. M. G. Bavin
    DOI:10.1139/v60-128
    日期:1960.6.1
    Methyl fluorene-9-carboxylate and 9-methyl-9-acetylfluorene have been nitrated and the products converted to 2-nitrophenanthrene and 2-nitro-9,10-dimethylphenanthrene, respectively.Acetylation of 9,10-dimethylphenanthrene has given only one ketone, probably the 3-isomer. 4-Nitrofluorenone has been synthesized by a convenient route.
    芴9-羧酸甲酯和9-甲基-9-乙酰芴已被硝化,产物分别转化为2-硝基菲和2-硝基-9,10-二甲基菲。9,10-二甲基菲乙酰化仅得到一个酮, 可能是 3-异构体。4-硝基芴酮已通过方便的路线合成。
  • [EN] COMPOUNDS FOR USE IN MODULATING THE NMDA RECEPTOR<br/>[FR] MODULATEURS POSITIFS ET NÉGATIFS DES RÉCEPTEURS NMDA
    申请人:UNIV NEBRASKA
    公开号:WO2012019106A8
    公开(公告)日:2012-09-27
  • ATTEMPTS TO FIND NEW ANTIMALARIALS. XII. DERIVATIVES OF PHENANTHRENE, IV. 1 (OR 8)-ACETYL-9-HALOPHENANTHRENE
    作者:J. SCHULTZ、M. A. GOLDBERG、E. P. ORDAS、G. CARSCH
    DOI:10.1021/jo01174a004
    日期:1946.7
  • STUDIES IN THE PHENANTHRENE SERIES. II. PHENANTHRENE CARBOXYLIC ACIDS AND 9-BROMOPHENANTHRENE DERIVATIVES<sup>1</sup>
    作者:Erich Mosettig、Jacob van de Kamp
    DOI:10.1021/ja01347a046
    日期:1932.8
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
hnmr
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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