3-bromo-5,6-dihydro-1-methylpyridin-2(1H)-one | 51263-41-3

• 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
• 英文名称: 3-bromo-5,6-dihydro-1-methylpyridin-2(1H)-one
• 英文别名: 5-Bromo-1-methyl-2,3-dihydropyridin-6-one
• CAS: 51263-41-3
• 化学式: C₆H₈BrNO
• 分子量: 190.04
• InChiKey: MAWBXPLOVHDGED-UHFFFAOYSA-N

物化性质

• 沸点：
  312.3±41.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-5,6-dihydro-1-methylpyridin-2(1H)-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 三甲基氯硅烷 、 噻吩-2-甲酸亚铜(I) 、 三苯胂 、 copper;N-[[(4R,5R)-2-[2-[(4R,5R)-4-(methanesulfonamidomethyl)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl]-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]methyl]methanesulfonamide;trifluoromethanesulfonate 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 19.5h， 生成 methyl ((4aS,8R,8aS)-6-((tert-butyldimethylsilyl)oxy)-8-methoxy-2-methyl-1-oxo-1,2,3,4,4a,5,8,8a-octahydroisoquinoline-8a-carbonyl)carbamate
  参考文献：
  名称：

  α-亚烷基β-酮亚胺的催化不对称[4 + 2]环加成反应和Hosomi-Sakurai反应

  摘要：

  描述了合理设计的α-亚烷基β-酮酰亚胺的高度对映选择性催化不对称反应。α-亚烷基β-酮酰亚胺的[4 + 2]环加成反应和Hosomi-Sakurai反应以高对映选择性和高收率进行。酰亚胺与各种二烯的[4 + 2]环加成反应提供的产物在环结处带有全碳四元立体异构中心。α-亚烷基β-酮酰亚胺应用于天然产物的对映选择性全合成和其他催化不对称应用。

  DOI：

  10.1021/ol303381c
• 作为产物：
  描述：

  1-methyl-3,3-dibromo-2-piperidone 在 calcium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到3-bromo-5,6-dihydro-1-methylpyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 5,6-dihydro-4H -benzo[d ]isoxazol-7-one and 5,6-dihydro-4H -isoxazolo[5,4-c ]pyridin-7-one Derivatives as Potential Hsp90 Inhibitors

  摘要：

  A novel class of 5,6‐dihydro‐4H‐benzo[d]isoxazol‐7‐ones and 5,6‐dihydro‐4H‐isoxazolo[5,4‐c]pyridin‐7‐ones was designed, synthesized, and assayed to investigate the affinity toward Hsp90 protein. The synthetic route was based on a 1,3‐dipolar cycloaddition of nitriloxides, generated in situ from suitable benzaldoximes, with 2‐bromocyclohex‐2‐enones or 3‐bromo‐5,6‐dihydro‐1H‐pyridin‐2‐ones. Whereas all the compounds bearing a benzamide group on the bicyclic scaffold were devoid of activity, the derivatives carrying a resorcinol‐like fragment showed a remarkable inhibitory effect on Hsp90. Docking calculations were performed to investigate the orientation of the new compounds within the binding site of the enzyme.

  DOI：

  10.1111/cbdd.12570

文献信息

• Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System
  作者：Masahisa Nakada、Katsuhiro Komuro、Aiichiro Nagaki、Hiroki Shimoda、Masahiro Uwamori、Jun-ichi Yoshida

  DOI：10.1055/s-0037-1610228

  日期：2018.9

  emphasized in the reaction of the organolithium compound with methoxycarbonyl isocyanate, which gave the desired imide in 78% yield by using the flow microreactor system whereas the yield of the corresponding batch reaction was only 2%. The established flow microreactor system was also effectively used for the reaction of the organolithium compound with phenyl isocyanate to afford the desired product in 52%

  描述了 3-iodo-1-methyl-5,6-dihydropyridin-2(1H)-one 通过卤素-锂交换和随后在流动微反应器系统中的反应成功转化为其衍生物。在流动微反应器系统中由 3-iodo-1-methyl-5,6-dihydropyridin-2(1H)-one 产生的有机锂化合物的甲基化以 68% 的产率提供了所需的甲基化产物，而相应批次的产率反应率为 23%。流动微反应器系统的这种优势在有机锂化合物与异氰酸甲氧基羰基酯的反应中得到进一步强调，使用流动微反应器系统以 78% 的收率得到所需的酰亚胺，而相应的间歇反应的收率仅为 2%。
• [EN] PIPERLONGUMINE-BASED COMPOUND AND IMMUNOMODULATOR COMPRSING SAME<br/>[FR] COMPOSÉ À BASE DE PIPERLONGUMINE ET IMMUNOMODULATEUR LE COMPRENANT<br/>[KO] 피페론구민계 화합물 및 이를 포함하는 면역조절제
  申请人：[en]HUSCION CO., LTD.;[ko]주식회사 휴사이온

  公开号：WO2022145707A1

  公开（公告）日：2022-07-07

  본 발명은 신규한 피페론구민계 화합물 및 상기 화합물, 이의 약학적으로 허용 가능한 염 또는 용매화물을 유효성분으로 포함하는 면역조절제, 면역조절용 건강기능식품을 제공한다.
• [EN] PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING VIRAL INFECTIONS CONTAINING PIPERLONGUMINE-BASED COMPOUND AS ACTIVE INGREDIENT<br/>[FR] COMPOSITION PHARMACEUTIQUE DESTINÉE À PRÉVENIR OU À TRAITER DES INFECTIONS VIRALES CONTENANT UN COMPOSÉ À BASE DE PIPERLONGUMINE UTILISÉ COMME PRINCIPE ACTIF<br/>[KO] 피페론구민계 화합물을 유효성분으로 포함하는 바이러스 감염증의 예방 또는 치료용 약학적 조성물
  申请人：[en]HUSCION CO., LTD.;[ko]주식회사 휴사이온

  公开号：WO2022145923A1

  公开（公告）日：2022-07-07

  본 발명은 피페론구민계 화합물을 유효성분으로 포함하는 바이러스 감염증의 예방 또는 치료용 약학적 조성물에 관한 것이다. 구체적으로, 본 발명에 따른 피페론구민계 화합물은 신종 코로나바이러스(SARS-CoV-2)의 감염을 저해함으로써, 바이러스의 감염, 특히 RNA 바이러스 감염증의 치료에 유용하게 사용될 수 있다.