7'-Methylspiro[cyclohexane-1,2'-pyrano[4,3-b]pyran]-5'-one | 220633-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 7'-Methylspiro[cyclohexane-1,2'-pyrano[4,3-b]pyran]-5'-one
• CAS: 220633-58-9
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: XAYVDPOFQAWONM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  7'-Methylspiro[cyclohexane-1,2'-pyrano[4,3-b]pyran]-5'-one 在 四氧化锇 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 以54%的产率得到(3R,4R)-3,4-dihydroxy-7-methylspiro[3,4-dihydropyrano[3,2-c]pyran-2,1'-cyclohexane]-5-one
  参考文献：
  名称：

  Stereoselective trans- and cis-Dihydroxylations of 2H-Pyranyl and Dihydropyridinyl Heterocycles Synthesized from Formal [3 + 3]-Cycloaddition Reactions of α,β-Unsaturated Iminium Ions with 1,3-Dicarbonyl Equivalents^†

  摘要：

  [GRAPHICS]We describe here an inherent problem in direct epoxidation of the endocyclic olefin in 2H-pyrans fused to 2-pyrones, Such difficulties led to the development of highly stereoselective trans- and cis-dihydroxylations of these olefinic systems in both 2H-pyrans and dihydropyridines fused to a 2-pyrones or a 2-cyclohexenone. Protocols for the removal of the activated allylic hydroxyl group are also reported.

  DOI：

  10.1021/ol010034r
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 环己基亚基乙醛 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 以86%的产率得到7'-Methylspiro[cyclohexane-1,2'-pyrano[4,3-b]pyran]-5'-one
  参考文献：
  名称：

  Sequential 1,2-Addition−Electrocyclic Ring Closures Involving Acyclic α,β-Unsaturated Iminiums:  A Formal [3 + 3] Cycloaddition Strategy to Unique Pyranyl Spirocycles

  摘要：

  DOI：

  10.1021/jo982165k

文献信息

• [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。
• Sequential 1,2-Addition−Electrocyclic Ring Closures Involving Acyclic α,β-Unsaturated Iminiums:  A Formal [3 + 3] Cycloaddition Strategy to Unique Pyranyl Spirocycles
  作者：Richard P. Hsung、Hong C. Shen、Christopher J. Douglas、Christopher D. Morgan、Shane J. Degen、Letitia J. Yao

  DOI：10.1021/jo982165k

  日期：1999.2.1
• Stereoselective <i>trans-</i> and <i>cis-</i>Dihydroxylations of 2<i>H</i>-Pyranyl and Dihydropyridinyl Heterocycles Synthesized from Formal [3 + 3]-Cycloaddition Reactions of α,β-Unsaturated Iminium Ions with 1,3-Dicarbonyl Equivalents^†
  作者：Luke R. Zehnder、Lin-Li Wei、Richard P. Hsung、Kevin P. Cole、Michael J. McLaughlin、Hong C. Shen、Heather M. Sklenicka、Jiashi Wang、Craig A. Zificsak

  DOI：10.1021/ol010034r

  日期：2001.7.1

  [GRAPHICS]We describe here an inherent problem in direct epoxidation of the endocyclic olefin in 2H-pyrans fused to 2-pyrones, Such difficulties led to the development of highly stereoselective trans- and cis-dihydroxylations of these olefinic systems in both 2H-pyrans and dihydropyridines fused to a 2-pyrones or a 2-cyclohexenone. Protocols for the removal of the activated allylic hydroxyl group are also reported.