2H-吡喃-2-酮,4-氯-6-甲基- | 17422-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2H-吡喃-2-酮,4-氯-6-甲基-
• 英文名称: 4-Chloro-6-methylpyran-2-one
• 英文别名: 4-chloro-6-methyl-2H-pyran-2-one；4-chloro-6-methyl-2-pyrone；4-Chlor-6-methyl-pyran-2-on
• CAS: 17422-72-9
• 化学式: C₆H₅ClO₂
• 分子量: 144.558
• InChiKey: RKJCPBWPPDKSHC-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C(Solv: water (7732-18-5))
• 沸点：
  230-232 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2H-吡喃-2-酮,4-氯-6-甲基- 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到4-azido-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  4-amino-6-methyl-2-pyran-2-one. Preparation and reactions with aromatic aldehydes

  摘要：

  DOI：

  10.1016/s0040-4020(01)90086-9
• 作为产物：
  描述：

  2,2-dimethyl-6-(2-oxopropyl)-4H-1,3-dioxin-4-one 在 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2H-吡喃-2-酮,4-氯-6-甲基-
  参考文献：
  名称：

  Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

  摘要：

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.084

文献信息

• Halogenated-2-pyrones in Sonogashira cross-coupling: limitations, optimisation and consequences for GC analysis of Pd-mediated reactions
  作者：Ian J.S. Fairlamb、Adam F. Lee、Faidjiba E.M. Loe-Mie、Elina H. Niemelä、Ciara T. O'Brien、Adrian C. Whitwood

  DOI：10.1016/j.tet.2005.07.102

  日期：2005.10

  (14) and to a lesser extent (E) and (Z)-ethyl 3-iodo-2-propenonate (16) under similar conditions. A more efficient quenching system (using excess dppe) has been developed to enable accurate determinations in product conversions. Alternatively, solvent and base (Et3N) removal in vacuo, or quench with saturated aqueous ammonium chloride, prevents further turnover in Sonogashira coupling. An ESI-MS study

  在CuI助催化剂的存在下，详细研究了Pd（PPh 3）2 Cl 2介导的4-溴-6-甲基-2-吡喃酮（5）与苯乙炔的Sonogashira偶联。Pd的浓度极大地影响了产品的产量，较低的Pd负载量有利于更高的转化率和更纯的交叉偶联产品。在仅用硅胶淬灭的样品（用CH 2 Cl 2洗脱）中观察到产物转化的后反应时间依赖性。在使用4-硝基溴苯（14）以及较小程度地（E）和（Z）-3-碘-2-丙酸乙酯（16）的反应中反映出了这种效果。）在相似的条件下。已经开发出了更有效的淬火系统（使用过量的dppe）以能够准确确定产品转化率。或者，在真空中除去溶剂和碱（Et 3 N），或用饱和氯化铵水溶液淬灭，可防止Sonogashira偶联剂进一步流失。对通过硅胶洗脱的样品进行了ESI-MS研究，以探讨可溶性Pd / Cu物质的性质。4-氯和6-氯-2-吡喃酮的Sonogashira交叉偶联（18和20，分别进行
• Palladium catalyzed C(sp²)–C(sp²) bond formation. A highly regio- and chemoselective oxidative Heck C-3 alkenylation of pyrones and pyridones
  作者：Hafiz Ul Lah、Faheem Rasool、Syed Khalid Yousuf

  DOI：10.1039/c5ra12631b

  日期：——

  Palladium catalysed ligand free direct dehydrogenative C-3 alkenylation of pyrones and unprotected pyridones from unactivated alkenes is reported. The process is highly regio- and chemoselective. A wide variety of alkene partners reacted to broaden the substrate scope of the process. The effect of the C-3 substituent on the rate of reaction is also studied.

  据报道，吡喃酮和未保护的吡啶酮不受未活化的烯烃的钯催化的无配体的直接脱氢C-3烯基化。该过程具有高度的区域选择性和化学选择性。各种各样的烯烃伙伴反应以扩大该方法的底物范围。还研究了C-3取代基对反应速率的影响。
• Synthesis of polyfluorinated indacenes – a new type of sterically hindered alkenes
  作者：Ireneusz Nowak

  DOI：10.1016/s0022-1139(99)00110-4

  日期：1999.10

  Sulfur tetrafluoride fluorinations of bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydrides provided an access to many polyfluorinated, polycyclic alkenes of a new structure. Factors responsible for the successful outcome include electronic character of substituents and reaction conditions. The thorough spectral analysis of isolated products led to the discovery of “through space” couplings

  双环[2.2.2] oct-7-ene-2,3,5,6-四羧酸二酐的四氟化硫氟化提供了许多新结构的多氟化多环烯烃的获得途径。导致成功结果的因素包括取代基的电子特性和反应条件。对分离出的产物进行彻底的光谱分析后，发现了“贯通空间”耦合，这表明由双键周围的氟原子引起的空间拥挤。
• Pyrrole derivatives useful for farnesyl transferase inhibitors and their preparations
  申请人：LG Life Sciences, Ltd.

  公开号：US06511978B1

  公开（公告）日：2003-01-28

  The present invention relates to a novel pyrrole derivative which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts or isomers thereof; to a process for preparation of said compound; and to a pharmaceutical composition such as anti-cancer composition, etc. comprising said compound as an active ingredient together with pharmaceutically acceptable carrier.

  本发明涉及一种新型吡咯衍生物，该衍生物显示出对法尼酰转移酶的抑制活性，或其药学上可接受的盐或异构体；以及制备该化合物的过程；以及包括该化合物作为活性成分的药物组合物，例如抗癌组合物等，以及药学上可接受的载体。
• Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins
  作者：Mario Di Braccio、Giancarlo Grossi、Giorgio Roma、Maria Grazia Signorello、Giuliana Leoncini

  DOI：10.1016/j.ejmech.2003.12.010

  日期：2004.5

  Pursuing our chemical and biological studies in this field, we described the multistep preparation of the new 5-, 6-, or 7-alkoxy and 7-alkoxy-8-methyl substituted 4-(1-piperazinyl)coumarins 5d-v, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187. Compounds 5h-j,p,r-u showed notably high activity towards all the platelet aggregation inducers used, and the most active one, 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin (5t), proved to be a potent in vitro antiplatelet agent. (C) 2004 Elsevier SAS. All rights reserved.