2-甲基-2,6,7,8-四氢-5H-苯并吡喃-5-酮 | 58133-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-2,6,7,8-四氢-5H-苯并吡喃-5-酮
• 英文名称: 2-methyl-2,6,7,8-tetrahydro-chromen-5-one
• 英文别名: 2-methyl-7,8-dihydro-2H-chromen-5(6H)-one；2-methyl-2,6,7,8-tetrahydrochromen-5-one；2-methyl-5,6,7,8-tetrahydro-2H-1-benzopyran-5-one
• CAS: 58133-98-5
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD08752420
• 分子量: 164.204
• InChiKey: TZDNUIAAQCSNHY-UHFFFAOYSA-N

物化性质

• 熔点：
  40-42 °C
• 沸点：
  95-96 °C(Press: 2 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-甲基-2,6,7,8-四氢-5H-苯并吡喃-5-酮 、 丙炔酸甲酯 以70%的产率得到
  参考文献：
  名称：

  SALOMON R. G.; BURNS J. R.; DOMINIC W. J., J. ORG. CHEM. , 1976, 41, NO 17, 2918-2920

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆醛 、 1,3-环己二酮 以 neat (no solvent) 为溶剂， 反应 8.0h， 以92%的产率得到2-甲基-2,6,7,8-四氢-5H-苯并吡喃-5-酮
  参考文献：
  名称：

  Microwave-Assisted Solvent and Catalyst Free Synthesis of 2H-Pyrans

  摘要：

  本文描述了一种简单高效的方法，利用多米诺克诺维纳格尔/$6{\pi}$电环化反应，在无溶剂和催化剂条件下通过微波辐射制备多种2H-吡喃。该方法具有绿色环保、高产率和短反应时间的优点。十六个化合物（9a-p）通过该过程以良好的至优异的产率获得。

  DOI：

  10.5012/bkcs.2013.34.10.2963

文献信息

• Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products
  作者：Ene Jin Jung、Byung Ho Park、Yong Rok Lee

  DOI：10.1039/c0gc00265h

  日期：——

  In water medium, environmentally benign, facile, and efficient synthesis of pyrans was achieved in good yields by the reactions of a variety of cyclic 1,3-dicarbonyls with several α,β-unsaturated aldehydes. The key strategy was a formal [3+3] cycloaddition by domino Knoevenagel/6π- electrocyclization. This methodology was applied to the synthesis of biologically interesting pyranocoumarin, pyranoquinolinone, and pyranonaphthoquinone derivatives along with selected natural and non-natural products.

  在水相介质中，通过多种环状1,3-二羰基化合物与若干α,β-不饱和醛的反应，以良好产率实现了吡喃的环保、简便、高效合成。关键策略是形式上的[3+3]环加成，通过多米诺Knoevenagel缩合/6π电环化反应实现。这一方法被应用于生物活性吡喃香豆素、吡喃喹啉酮和吡喃萘醌衍生物的合成，以及部分天然与合成产物的制备。
• 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。
• Lipase-catalyzed regioselective domino reaction for the synthesis of chromenone derivatives
  作者：Qi Yang、Long-Hua Zhou、Wan-Xia Wu、Wei Zhang、Na Wang、Xiao-Qi Yu

  DOI：10.1039/c5ra13267c

  日期：——

  An efficient synthesis of 2H-chromenones and 2-hydroxyl-2H-chromenones derivatives has been developed from 1,3-dicarbonyls and α,β-unsaturated aldehydes by a controllable regioselective domino cyclization reaction under catalysis of different lipases. 2H-Chromenones derivatives were synthesized by bovine pancreatic lipase (BPL) in acetonitrile, while lipase from Pseudomonas fluorescens (PFL) can catalyze

  为2个的有效的合成ħ -chromenones和2-羟基-2- ħ -chromenones衍生物已经从1,3-二羰基和α，β不饱和醛通过在不同脂肪酶催化的可控区域选择性多米诺环化反应的发展。2 H- Chromenones衍生物是由牛胰脂肪酶（BPL）在乙腈中合成的，而荧光假单胞菌（PFL）的脂肪酶则可以在二氯甲烷中以中等至高收率催化2-hydroxyl-2 H -chromenones衍生物的合成。
• Benzo[A] [phenazin-11-carboxamide derivatives and their use as joint inhibitors of topomerase I and II
  申请人：——

  公开号：US20030139409A1

  公开（公告）日：2003-07-24

  A compound which is a benzo[a]phenazine-11-carboxamide derivative of formula (I) wherein each of R 1 to R 4 , which are the same or different, is selected from hydrogen, halogen, hydroxyl, C 1 -C 6 alkoxy which is unsubstituted or substituted, heteroaryloxy, C 1 -C 6 alkyl which is unsubstituted or substituted, nitro, cyano, azido, amidoxime, CO 2 R 10 , CON(R 12 ) 2 , OCON(R 12 ), SR 10 , SOR 11 , SO 2 (R 11 ), SO 2 N(R 12 ) 2 , N(R 12 ) 2 , NR 10 SO 2 R 11 , N(SO 2 R 11 ) 2 NR 10 (CH 2 ) n CN, NR 10 COR 11 , OCOR 11 or COR 10 ; each of R 5 to R 7 , which are the same or different, is selected from hydrogen, halogen, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, SR 10 and N(R 12 ) 2 ; Q is C 1 -C 6 alkylene which is unsubstituted or substituted by (i) C 1 -C 6 alkyl which is unsubstituted or substituted, (ii) hydroxy, provided that the hydroxy group is not, to either of the N atoms adjacent to Q in formula (I), (iii) CO 2 R 10 , or (iv) CON(R 12 ); R 1 and R 9 , which are the same or different, are each hydrogen or C 1 -C 6 alkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a saturated 5- or 6-membered N-containing heterocyclic ring which may include one additional heteroatom selected from O, N and S, or one of R 8 and R 9 is an alkylene chain optionally interrupted by O, N or S, which is attached to a carbon atom on the alkylene chain represented by Q to complete a saturated 5- or 6-membered N-containing heterocyclic ring as defined above; or a pharmaceutically acceptable salt thereof; with the proviso that at least one R 1 to R 4 is other than hydrogen. These compounds are inhibitors of topoisomerase I and/or topoisomerase II and can be used to treat tumours, including tumours which express MDR.

  一种化合物，是一种公式（I）的苯并[a]菲啉-11-甲酰胺衍生物，其中R1至R4中的每一个，它们相同或不同，被选择为氢、卤素、羟基、未取代或取代的C1-C6烷氧基、杂环氧基、未取代或取代的C1-C6烷基、硝基、氰基、叠氮基、酰肼基、CO2R10、CON(R12)2、OCON(R12)、SR10、SOR11、SO2(R11)、SO2N(R12)2、N(R12)2、NR10SO2R11、N(SO2R11)2NR10(CH2)nCN、NR10COR11、OCOR11或COR10；R5至R7中的每一个，它们相同或不同，被选择为氢、卤素、羟基、C1-C6烷氧基、C1-C6烷基、SR10和N(R12)2；Q是未取代或取代的C1-C6烷基，其被（i）未取代或取代的C1-C6烷基，（ii）羟基、前提是羟基不是在公式（I）中与Q相邻的任一N原子，（iii）CO2R10，或（iv）CON(R12)所取代；R1和R9，它们相同或不同，分别是氢或C1-C6烷基，或R8和R9连同它们连接到的氮原子形成饱和的5-或6-成员N-含杂环戊或六元环，可能包括一个额外的由O、N和S中选择的杂原子，或R8和R9中的一个是由O、N或S随机中断的烷基链，它连接到由Q表示的烷基链上的碳原子，以完成上述定义的饱和的5-或6-成员N-含杂环戊或六元环；或其药学上可接受的盐；但至少一个R1到R4不是氢。这些化合物是拓扑异构酶I和/或拓扑异构酶II的抑制剂，可用于治疗肿瘤，包括表达MDR的肿瘤。
• 2-(1-azabicyclo[2.2.2]oct-3 s-yl)-6-hydroxy-2,4,5,6-tetrahydro-1H-benz[DE]i
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05492914A1

  公开（公告）日：1996-02-20

  This invention relates to 2-(1'-azabicyclo[2.2.2]oct-3'S-yl)-6-hydroxy-2,4,5,6-tetrahydro-1H-benz[de ]isoquinolin-1-one and 2-(1'-azabicyclo[2.2.2]oct-3'S-yl)-6-hydroxy-2,3,3a,4,5,6-hexahydro-1H-ben z[de]isoquinolin-1-one and their individual stereoisomers and uses and the processes for their making.

  本发明涉及2-(1'-azabicyclo[2.2.2]oct-3'S-yl)-6-羟基-2,4,5,6-四氢-1H-苯[de]异喹啉-1-酮和2-(1'-azabicyclo[2.2.2]oct-3'S-yl)-6-羟基-2,3,3a,4,5,6-六氢-1H-苯[de]异喹啉-1-酮及其各个立体异构体、用途和制备过程。