2,2,7-三甲基-2H-吡喃并[4,3-b]吡喃-5-酮 | 220633-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2,2,7-三甲基-2H-吡喃并[4,3-b]吡喃-5-酮
• 英文名称: 2,2,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one
• 英文别名: 2,2,7-trimethylpyrano[4,3-b]pyran-5-one
• CAS: 220633-52-3
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD08752456
• 分子量: 192.214
• InChiKey: HXXIFLAWGKQKAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,7-三甲基-2H-吡喃并[4,3-b]吡喃-5-酮 在 二甲基二环氧乙烷 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以63%的产率得到(3R,4S)-3,4-Dihydroxy-2,2,7-trimethyl-3,4-dihydro-2H-pyrano[4,3-b]pyran-5-one
  参考文献：
  名称：

  Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

  摘要：

  An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-0-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.022
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 3-甲基-2-丁烯醛 在 2,4,8,10-tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 以99%的产率得到2,2,7-三甲基-2H-吡喃并[4,3-b]吡喃-5-酮
  参考文献：
  名称：

  布朗斯台德酸通过正式的[3 + 3]环加成反应合成吡喃

  摘要：

  布朗斯台德酸通过正规的[3 + 3]环加成反应，在温和的条件下以高收率催化将可烯化的β-酮酯加成到α，β-不饱和醛上，从而以高收率生成取代的2H-吡喃。

  DOI：

  10.1002/adsc.200700375

文献信息

• Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2<i>H</i>-Chromenones, Pyranones, and Tetrahydroquinolinones
  作者：Julie Moreau、Claudie Hubert、Jessika Batany、Loic Toupet、Thierry Roisnel、Jean-Pierre Hurvois、Jean-Luc Renaud

  DOI：10.1021/jo901238y

  日期：2009.12.4

  Brønsted acids catalyze the addition of enolizable β-diketones, β-ketoesters, and vinylogous amides to α,β-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetrahydroquinolinones in good yields under mild reaction conditions via a formal [3 + 3] cycloaddition.

  布朗斯台德酸通过形式化的[3 + 3]在温和的反应条件下催化将可烯化的β-二酮，β-酮酸酯和乙烯基酰胺添加到α，β-不饱和醛中，从而以高收率生成取代的色农酮，吡喃酮和四氢喹啉酮。环加成。
• Brønsted Acid‐Catalyzed Synthesis of Pyrans <i>via</i> a Formal [3+3] Cycloaddition
  作者：Claudie Hubert、Julie Moreau、Jessika Batany、Agathe Duboc、Jean‐Pierre Hurvois、Jean‐Luc Renaud

  DOI：10.1002/adsc.200700375

  日期：2008.1.4

  Brønsted acids catalyze the addition of enolizable β-keto esters to α,β-unsaturated aldehydes leading to substituted 2H-pyrans in good yields under mild conditions via a formal [3+3] cycloaddition.

  布朗斯台德酸通过正规的[3 + 3]环加成反应，在温和的条件下以高收率催化将可烯化的β-酮酯加成到α，β-不饱和醛上，从而以高收率生成取代的2H-吡喃。
• [EN] PYRANOPYRANONE DERIVATIVES AS ANTIMICROBIAL AGENTS<br/>[FR] DÉRIVÉS DE PYRANOPYRANONE COMME AGENTS ANTIMICROBIENS
  申请人：BASF SE

  公开号：WO2011107411A1

  公开（公告）日：2011-09-09

  Disclosed is the use of pyranopyranone derivatives of formula (1), wherein R1, R2, R3, R4 and R5 independently of one another are hydrogen; C1-C30alkyl, C2-C30alkenyl, or C3-C12cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2-C18alkenyl, C2-10 C18alkynyl, C7-C25aralkyl, or -CO-R6; -SiR8 R9R10; or R4 and R5 together form a five or six membered ring; or R3 and R4 together form a five or six membered ring; D is -CO-; -COO-; -S-; -SO-; -SO2-; -O-; -NR7-; -SiR8R9-; -POR10-; -CR12=CR13-; or -C≡C-; and E is OR6; -SR6; -NR14R15; -NR14COR15; -COR6; -COOR6; -CONR14R15; -CN; halogen; or OSO3R11; SO3R11; SO2R11; PO3(R11)2; OPO3(R11)2; G is E; C1-C18alkyl, which is optionally interrupted by D; C1-C18perfluoroalkyl; C1-C18alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R6 is H; C6-C18aryl which is optionally substituted by OH, C1-C30alkyl or C1-C30alkoxy; or C1-C30alkyl which is optionally interrupted by O-; R7 is H; C6-C18aryl which is optionally substituted by OH, C1-C30alkyl or C1-C30alkoxy; or C1-C30alkyl which is optionally interrupted by O-; R8, R9 and R10 independently of each other are hydrogen; C1-C30alkyl; C6-C18aryl which is optionally substituted by C1-C30alkyl; and R11 is hydrogen; C6-C18aryl, which is optionally substituted by OH, C1-C30alkyl or C1- C30alkoxy; or C1-C30alkyl, which is optionally interrupted by O-; R12, R13, R14 and R15 independently of each other are hydrogen; C6-C18aryl which is optionally substituted by OH, C1-C30alkyl or C1-C30alkoxy; C1-C30alkyl, which is optionally interrupted by O-; or R14 and R15 together form a five or six membered ring; as antimicrobial and/or preserving agents.

  本发明揭示了使用式（1）的吡喃并吡喃酮衍生物，其中R1、R2、R3、R4和R5独立地为氢；C1-C30烷基，C2-C30烯基或C3-C12环烷基，可以由一个或多个E取代和/或由一个或多个D中断；C6-C20芳基，可以由一个或多个G取代；C4-C20杂芳基，可以由一个或多个G和/或C2-C18烯基，C2-10 C18炔基，C7-C25芳基烷基或-CO-R6取代；-SiR8R9R10；或R4和R5共同形成五元或六元环；或R3和R4共同形成五元或六元环；D为-CO-；-COO-；-S-；-SO-；-SO2-；-O-；-NR7-；-SiR8R9-；-POR10-；-CR12=CR13-；或-C≡C-；E为OR6；-SR6；-NR14R15；-NR14COR15；-COR6；-COOR6；-CONR14R15；-CN；卤素；或OSO3R11；SO3R11；SO2R11；PO3（R11）2；OPO3（R11）2；G为E；C1-C18烷基，可以由D中断；C1-C18全氟烷基；C1-C18烷氧基，可以由E取代和/或由D中断；其中R6为H；C6-C18芳基，可以选择性地由OH，C1-C30烷基或C1-C30烷氧基取代；或者C1-C30烷基，可以选择性地由O-中断；R7为H；C6-C18芳基，可以选择性地由OH，C1-C30烷基或C1-C30烷氧基取代；或者C1-C30烷基，可以选择性地由O-中断；R8、R9和R10独立地为氢；C1-C30烷基；C6-C18芳基，可以选择性地由C1-C30烷基取代；R11为氢；C6-C18芳基，可以选择性地由OH，C1-C30烷基或C1-C30烷氧基取代；或C1-C30烷基，可以选择性地由O-中断；R12、R13、R14和R15独立地为氢；C6-C18芳基，可以选择性地由OH，C1-C30烷基或C1-C30烷氧基取代；C1-C30烷基，可以选择性地由O-中断；或者R14和R15共同形成五元或六元环；作为抗菌和/或防腐剂。
• Pyranopyranone derivatives as antimicrobial agents
  申请人：Wagner Barbara

  公开号：US20110224170A1

  公开（公告）日：2011-09-15

  Disclosed is the use of pyranopyranone derivatives of formula wherein R 1 , R 2 , R 3 , R 4 and R 5 independently of one another are hydrogen; C 1 -C 30 alkyl, C 2 -C 30 alkenyl, or C 3 -C 12 cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, or —CO—R 6 ; —SiR 8 R 9 R 10 ; or R 4 and R 5 together form a five or six membered ring; or R 3 and R 4 together form a five or six membered ring; D is —CO—; —COO—; —S—; —SO—; —SO 2 —; —O—; —NR 7 —; —SiR 8 R 9 —; —POR 10 —; —CR 12 ═CR 13 —; or —C≡C—; and E is —OR 6 ; —SR 6 ; —NR 14 R 15 ; —NR 14 COR 15 ; —COR 6 ; —COOR 6 ; —CONR 14 R 15 ; —CN; halogen; or OSO 3 R 11 ; SO 3 R 11 ; SO 2 R 11 ; PO 3 (R 11 ) 2 ; OPO 3 (R 11 ) 2 ; G is E; C 1 -C 18 alkyl, which is optionally interrupted by D; C 1 -C 18 perfluoroalkyl; C 1 -C 18 alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R 6 is H; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 30 alkyl or C 1 -C 30 alkoxy; or C 1 -C 30 alkyl which is optionally interrupted by —O—; R 7 is H; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 30 alkyl or C 1 -C 30 alkoxy; or C 1 -C 30 alkyl which is optionally interrupted by —O—; R 8 , R 9 and R 10 independently of each other are hydrogen; C 1 -C 30 alkyl; C 6 -C 18 aryl which is optionally substituted by C 1 -C 30 alkyl; and R 11 is hydrogen; C 6 -C 18 aryl, which is optionally substituted by OH, C 1 -C 30 alkyl or C 1 -C 30 alkoxy; or C 1 -C 30 alkyl, which is optionally interrupted by —O—; R 12 , R 13 , R 14 and R 15 independently of each other are hydrogen; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 30 alkyl or C 1 -C 30 alkoxy; C 1 -C 30 alkyl, which is optionally interrupted by —O—; or R 14 and R 15 together form a five or six membered ring; as antimicrobial and/or preserving agents.

  本发明涉及使用式（I）的吡喃并吡喃酮衍生物，其中R1、R2、R3、R4和R5独立地为氢；C1-C30烷基，C2-C30烯基或C3-C12环烷基，可以被一个或多个E取代和/或被一个或多个D打断；C6-C20芳基，可以被一个或多个G取代；C4-C20杂环芳基，可以被一个或多个G取代，C2-C18烯基，C2-C18炔基，C7-C25芳基烷基或-CO-R6；-SiR8R9R10；或R4和R5一起形成五元或六元环；或R3和R4一起形成五元或六元环；D是-CO-；-COO-；-S-；-SO-；-SO2-；-O-；-NR7-；-SiR8R9-；-POR10-；-CR12═CR13-；或-C≡C-；E是-OR6；-SR6；-NR14R15；-NR14COR15；-COR6；-COOR6；-CONR14R15；-CN；卤素；或OSO3R11；SO3R11；SO2R11；PO3（R11）2；OPO3（R11）2；G是E；C1-C18烷基，可选地被D打断；C1-C18全氟烷基；C1-C18烷氧基，可选地被E取代和/或被D打断；其中R6是H；C6-C18芳基，可选地被OH，C1-C30烷基或C1-C30烷氧基取代；或C1-C30烷基，可选地被-O-打断；R7是H；C6-C18芳基，可选地被OH，C1-C30烷基或C1-C30烷氧基取代；或C1-C30烷基，可选地被-O-打断；R8、R9和R10独立地为氢；C1-C30烷基；C6-C18芳基，可选地被C1-C30烷基取代；R11为氢；C6-C18芳基，可选地被OH，C1-C30烷基或C1-C30烷氧基取代；或C1-C30烷基，可选地被-O-打断；R12、R13、R14和R15独立地为氢；C6-C18芳基，可选地被OH，C1-C30烷基或C1-C30烷氧基取代；C1-C30烷基，可选地被-O-打断；或R14和R15一起形成五元或六元环；作为抗微生物和/或保藏剂。
• A Lewis Acid-Catalyzed Formal [3 + 3] Cycloaddition of α,β-Unsaturated Aldehydes with 4-Hydroxy-2-Pyrone, Diketones, and Vinylogous Esters
  作者：Aleksey V. Kurdyumov、Nan Lin、Richard P. Hsung、Glen C. Gullickson、Kevin P. Cole、Nadiya Sydorenko、Jacob J. Swidorski

  DOI：10.1021/ol0523042

  日期：2006.1.1

  A Lewis acid-catalyzed formal cycloaddition of alpha,beta-unsaturated aldehydes with 6-methyl-4-hydroxy-2-pyrone, 1,3-diketones, and vinylogous silyl esters is described here.