2,2,6-三甲基-3H-吡喃-4-酮 | 16080-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2,2,6-三甲基-3H-吡喃-4-酮
• 英文名称: 2,2,6-trimethyl-2,3-dihydro-4H-pyran-4-one
• 英文别名: 2,3-dihydro-2,2,6-trimethyl-4H-pyran-4-one；2,6,6-trimethyl-5,6-dihydro-4H-pyran-4-one；2,2,6-trimethyl-2,3-dihydro-4-pyranone；dihydro-2,3-trimethyl-2,2,6-pyrone-4；2,2,6-trimethyl-2H-pyran-4(3H)-one；methyl pyranone；2,2,6-trimethyl-3H-pyran-4-one
• CAS: 16080-27-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: ZCHCAGXPCLIZMW-UHFFFAOYSA-N

物化性质

• 沸点：
  93-94 °C(Press: 11 Torr)
• 密度：
  1.006 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2,2,6-三甲基-3H-吡喃-4-酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 6-methyl-hept-5-ene-2,4-dione
  参考文献：
  名称：

  Gelin,S.; Gelin,R., Bulletin de la Societe Chimique de France, 1968, p. 288 - 298

  摘要：

  DOI：
• 作为产物：
  描述：

  6-hydroxy-6-methyl-2,4-heptanedione 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 以45%的产率得到2,2,6-三甲基-3H-吡喃-4-酮
  参考文献：
  名称：

  Peterson, John R.; Winter, Tamara J.; Miller, Chris P., Synthetic Communications, 1988, vol. 18, # 9, p. 949 - 964

  摘要：

  DOI：

文献信息

• A solvent-free amidation of vinylogous esters via direct aziridination
  作者：Emily C. McLaughlin、Anuska Shrestha、Madison H. Fletcher、Nathaniel S. Steinauer、Min Kyung Shinn、Sabrina M. Shahid

  DOI：10.1016/j.tetlet.2013.07.135

  日期：2013.10

  A microwave-mediated aziridination of α,β-unsaturated ketones and esters through the decomposition of ethyl azidoformate has been developed. When the same atom-economical reaction conditions are applied to cyclic vinylogous esters, N-functionalization at the α-position occurs. Based on NMR analysis, these amidation products appear to be formed from the desired aziridine in moderate to good yields.

  通过叠氮甲酸乙酯的分解，对α，β-不饱和酮和酯进行了微波介导的叠氮化。当将相同的原子经济反应条件应用于环状乙烯基酯时，在α位发生N-官能化。基于NMR分析，这些酰胺化产物似乎由所需的氮丙啶以中等至良好的产率形成。
• A New General Synthesis of 2,2-Dialkyl-2,3-dihydro-4H-pyran-4-ones and Their Application for thein situ Preparation of Electron-Rich Dienes in Carbonyl-Alkyne Exchange Reactions with Acetylenes
  作者：Daniel Obrecht

  DOI：10.1002/hlca.19910740106

  日期：1991.1.30

  reactions with electron-poor alkynes VII to yield the highly substituted aromatic compounds VIII and IX. These reactions proceed in good yields and with excellent degree of regioselectivity. Aryl-substituted 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones III (R1 = Ar) subsequently yield highly substituted biaryls. Reaction mechanisms are presented for the formation of the 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones

  II和III型取代的2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮是通过酸催化环化相应的取代炔基酮I制备的，收率良好至优异（方案1）。这些2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮II和III已用于在羰基炔烃交换中原位制备IV - VI型高反应性二烯（方案2）与贫电子炔烃VII反应生成高度取代的芳族化合物VIII和IX。这些反应以良好的收率和优异的区域选择性进行。芳基取代的2，2-二烷基-2，3-二氢-4 H-吡喃-4-酮III（R 1＝ Ar）随后产生高度取代的联芳基。提出了形成2，2-二烷基-2，3-二氢-4 H-吡喃-4-酮以及与贫电子乙炔的羰基炔交换反应的反应机理。
• Brønsted Acid Catalyzed Cycloisomerizations of 5,2-Enyne-1-ones: Highly Regioselective Synthesis of 2,3-Dihydro-4<i>H</i>-pyran-4-ones
  作者：Fang Yang、Ke-Gong Ji、Shu-Chun Zhao、Shaukat Ali、Yu-Ying Ye、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1002/chem.201103771

  日期：2012.5.21

  Dual‐action catalyst: A Brønsted acid catalyzed regioselective cycloisomerization was found to be highly effective for the preparation of structurally diverse 2,3‐dihydro‐4H‐pyran‐4‐ones in a 6‐exo‐trig manner from the corresponding 5,2‐enyne‐1‐ones. In this reaction, the Brønsted acid acts as a dual catalyst activating both the carbonyl and alkene moieties in a cascade manner (see scheme).

  双作用催化剂：布朗斯台德酸催化的区域选择性环异构被认为是用于制备非常有效的结构不同的2,3-二氢-4- ħ -吡喃-4-酮在6-外型-trig方式从相应的5-， 2炔1酮 在该反应中，布朗斯台德酸作为双重催化剂以级联方式激活羰基和烯烃部分（参见方案）。
• Photocyclodimerization of 5-Methyl-2<i>H</i>-pyran-3(6<i>H</i>)-one
  作者：Ljubov Groesch、Jürgen Kopf、Paul Margaretha

  DOI：10.1002/hlca.200890239

  日期：2008.12

  The structures of the main products resulting from photocyclodimerization of the title compound 2 and of other 3-methyl-substituted ‘oxacyclohex-2-en-1-ones’ (=dihydropyranones) were determined by X-ray crystallography. In connection, the 13C-NMR chemical shifts of the cyclobutane C-atoms of these dimers allow a clear differentiation between head-to-head and head-to-tail regioisomers, all structurally

  由标题化合物2和其他3-甲基取代的“氧杂环己-2-烯-1-酮”（＝二氢吡喃酮）的光环二聚作用产生的主要产物的结构通过X射线晶体学测定。与此相关，这些二聚体的环丁烷C原子的13 C-NMR化学位移可实现头对头和头对尾区域异构体之间的清晰区分，所有这些结构异构体均与异佛尔酮（1）相关。
• Red organic electroluminescent devices
  申请人：EASTMAN KODAK COMPANY

  公开号：EP1351322A1

  公开（公告）日：2003-10-08

  An organic EL device, having an anode and a cathode, and at least one organic luminescent medium including a compound of the formula: wherein: R1, and R2 are individually alkyl of from 1 to 20 carbon atoms, aryl, substituted aryl, carbocyclic and other heterocyclic systems; and R1, and R2 can be connected to form 5 or 6 member ring systems; and R3, and R4 are individually hydrogen; alkyl of from 1 to 10 carbon atoms, and a branched or unbranched 5 or 6 member substituent ring connecting with R1, R2 respectively; and R5 and R6 are individually hydrogen; alkyl of from 1 to 20 carbon atoms; aryl and heteroaryl of from 5 to 24 carbon atoms; and R6 can be connected with R5 to form a branched or unbranched 5 or 6 member carbocyclic ring.

  一种有机电致发光器件，具有阳极和阴极，以及至少一种包括式化合物的有机发光介质： 其中 R1和R2分别为1至20个碳原子的烷基、芳基、取代芳基、碳环和其它杂环系统；R1和R2可连接形成5或6个成员的环系统；R3和R4分别为氢；R5 和 R6 分别为氢、1-20 个碳原子的烷基、5-24 个碳原子的芳基和杂芳基；R6 可与 R5 连接形成支链或未支链的 5 或 6 个碳环。