2-溴-6-甲基吡啶-3-甲醛 | 853179-74-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-溴-6-甲基吡啶-3-甲醛
• 中文别名: 2-溴-6-甲基吡啶-3-羧醛
• 英文名称: 2-bromo-6-methylpyridine-3-carbaldehyde
• 英文别名: 2-bromo-3-formyl-6-methyl pyridine；2-Bromo-6-methylnicotinaldehyde
• CAS: 853179-74-5
• 化学式: C₇H₆BrNO
• 分子量: 200.035
• InChiKey: MQSSRBWNPRWQRS-UHFFFAOYSA-N

物化性质

• 熔点：
  66℃
• 沸点：
  273.5±35.0 °C(Predicted)
• 密度：
  1.577

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331

反应信息

• 作为反应物：
  描述：

  2-溴-6-甲基吡啶-3-甲醛 在 sodium tetrahydroborate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (2-Bromo-6-methylpyridin-3-yl)methyl-triphenylphosphanium;bromide
  参考文献：
  名称：

  A new approach to the 1,10-phenanthroline core

  摘要：

  A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of eiv-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinalclehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.073
• 作为产物：
  描述：

  2-溴-3-氰基-6-甲基吡啶 在 二异丁基氢化铝 、 硫酸 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 18.5h， 以93%的产率得到2-溴-6-甲基吡啶-3-甲醛
  参考文献：
  名称：

  Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone

  摘要：

  Heck vinylation of 2-bromo-6-methyl-3-substituted pyridines using eta(3)-allylpalladium chloride dimer/P(o-Tol)(3) complex/toluene and dimethylacetamide (DMA) as co-solvent with methyl acrylate is reported. Electronic and steric effects were investigated engaging diversely 2-bromo-3,6-disubstituted pyridines. As application, a new synthesis of the 6-methyl cyclopenta[b]pyridinone building-block connecting Heck vinylation, alkene reduction and Dieckmann condensation is described. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.03.008

文献信息

• Synthesis of stereodefined 1-aryl(heteroaryl) substituted 1,2-bis(2-bromopyridin-3-yl)ethenes by selective tandem Suzuki–Miyaura cross-coupling reactions
  作者：Giorgio Chelucci、Salvatore Baldino

  DOI：10.1016/j.tetlet.2008.02.149

  日期：2008.4

  A protocol for the synthesis of stereodefined 1-aryl(heteroaryl) substituted 1,2-bis(2-bromopyridin-3-yl)ethenes by tandem Suzuki–Miyaura cross-coupling reactions and an example of convention into 5-phenyl-1,10-phenanthroline are described.

  串联铃木-宫浦交叉偶联反应合成立体定义的1-芳基（杂芳基）取代的1，2-双（2-溴吡啶基-3-基）乙烯的规程，以及将规例转化为5-苯基-1的例子，描述了10-菲咯啉。
• [EN] GHRELIN O-ACYLTRANSFERASE INHIBITORS<br/>[FR] INHIBITEURS DE LA GHRÉLINE O-ACYLTRANSFÉRASE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019149959A1

  公开（公告）日：2019-08-08

  This invention relates to novel compounds according to Formula (I) which are inhibitors of ghrelin O-acyltransferase (GOAT), to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy for the treatment of metabolic disorders (e.g. Prader-Willi syndrome, metabolic syndrome, insulin resistance, impaired glucose tolerance, prediabetes, diabetes mellitus (e.g., type II diabetes mellitus), dysglycemia (e.g., hyperglycemia), obesity (e.g., obesity caused by Prader-Willi syndrome), increased adiposity, poor glycemic control, hyperphagia, impaired satiety, dyslipidemia (e.g., atherogenic dyslipidemia), hepatic steatosis (e.g., non-alcoholic fatty liver disease (e.g., non-alcoholic steatohepatitis))), psychiatric disorders (e.g., eating disorders (e.g., bulimia nervosa, binge eating disorder, night-time eating syndrome), substance related disorders (e.g., addiction disorders (e.g., alcohol, smoking, overeating, or use of illicit drugs))), as well as disorders related to or complications of metabolic or psychiatric disorders (e.g., cardiovascular diseases (e.g., diabetic heart disease (e.g., diabetic cardiomyopathy), heart failure, or hypertension), ischemia (e.g., myocardial ischemia, cerebral ischemia, ischemic stroke), or BMI-related cancers (e.g., pancreatic cancer, gallbladder cancer, esophageal cancer, colorectal cancer, breast cancer etc.).

  本发明涉及一种新型化合物，其具有公式（I）所示的结构，可作为胃饥饿素O-酰基转移酶（GOAT）的抑制剂，以及包含它们的制药组合物、它们的制备方法，以及它们在治疗代谢性疾病（例如普拉德-威利综合征、代谢综合征、胰岛素抵抗、糖耐量受损、糖尿病（例如2型糖尿病）、血糖异常（例如高血糖）、肥胖症（例如由普拉德-威利综合征引起的肥胖症）、增加的脂肪含量、差劲的血糖控制、暴食、饱腹感受障碍、血脂异常（例如致动脉粥样硬化的血脂异常）、肝脂肪变性（例如非酒精性脂肪肝病（例如非酒精性脂肪性肝炎）））、精神障碍（例如饮食障碍（例如暴食症、厌食症、夜间进食综合征）、物质相关障碍（例如成瘾障碍（例如酒精、吸烟、暴饮暴食或使用非法药物））），以及与代谢或精神障碍相关或并发的疾病（例如心血管疾病（例如糖尿病性心脏病（例如糖尿病性心肌病）、心力衰竭或高血压）、缺血（例如心肌缺血、脑缺血、缺血性中风）或与BMI相关的癌症（例如胰腺癌、胆囊癌、食管癌、结直肠癌、乳腺癌等）的治疗中使用。
• Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone
  作者：Nicolas Robert、Christophe Hoarau、Sylvain Célanire、Pierre Ribéreau、Alain Godard、Guy Quéguiner、Francis Marsais

  DOI：10.1016/j.tet.2005.03.008

  日期：2005.5

  Heck vinylation of 2-bromo-6-methyl-3-substituted pyridines using eta(3)-allylpalladium chloride dimer/P(o-Tol)(3) complex/toluene and dimethylacetamide (DMA) as co-solvent with methyl acrylate is reported. Electronic and steric effects were investigated engaging diversely 2-bromo-3,6-disubstituted pyridines. As application, a new synthesis of the 6-methyl cyclopenta[b]pyridinone building-block connecting Heck vinylation, alkene reduction and Dieckmann condensation is described. (c) 2005 Published by Elsevier Ltd.
• A new approach to the 1,10-phenanthroline core
  作者：Giorgio Chelucci、Daniele Addis、Salvatore Baldino

  DOI：10.1016/j.tetlet.2007.03.073

  日期：2007.5

  A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of eiv-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinalclehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained. (c) 2007 Elsevier Ltd. All rights reserved.