7-(acetylamino)-2,2-dimethyl-2H-1-benzopyran | 79014-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-(acetylamino)-2,2-dimethyl-2H-1-benzopyran
• 英文别名: 7-Acetamido-2,2-dimethyl-2H-chromene；7-Acetylaminochromene；7-acetamido-2,2-dimethyl-2H-benzo[b]pyran；7-acetoamino-2,2-dimethyl-6-2H-1-benzopyran；N-(2,2-Dimethyl-2H-1-benzopyran-7-yl)acetamide；N-(2,2-dimethylchromen-7-yl)acetamide
• CAS: 79014-11-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: QNYIOCDNXGPDPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(acetylamino)-2,2-dimethyl-2H-1-benzopyran 在 盐酸 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 2-(2,2-Dimethyl-2H-chromen-7-ylamino)-6-methyl-1,4-benzoquinone
  参考文献：
  名称：

  Synthesis of some carbazolequinone alkaloids and their analogues. Facile palladium-assisted intramolecular ring closure of arylamino-1,4-benzoquinones to carbazole-1,4-quinones.

  摘要：

  碳唑醌生物碱、毛果杨梅醌-A（1a）、 pyrayaquinone-A（2）和-B（3），以及吡喃[3, 2-b]碳唑醌5（2和3的异构体），通过钯催化的分子内环闭合反应，便捷地从相应的2-芳基氨基-甲基-1, 4-苯醌（9a和9i-k）合成而成。此外，还以相同的方法合成了系列类似物，包括6-、7-和8-取代的3-甲基碳唑-1, 4-醌衍生物（1b-g）以及与1a-g对应的2-甲基碳唑醌（6a-g）。碳-13核磁共振谱的比较分析提供了对2-或3-甲基碳唑醌结构分配的有用信息。

  DOI：

  10.1248/cpb.39.328
• 作为产物：
  描述：

  N-(3-羟基苯基)乙酰胺 在 水 、 potassium carbonate 、 N,N-二乙基苯胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 98.0h， 生成 7-(acetylamino)-2,2-dimethyl-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis of some carbazolequinone alkaloids and their analogues. Facile palladium-assisted intramolecular ring closure of arylamino-1,4-benzoquinones to carbazole-1,4-quinones.

  摘要：

  碳唑醌生物碱、毛果杨梅醌-A（1a）、 pyrayaquinone-A（2）和-B（3），以及吡喃[3, 2-b]碳唑醌5（2和3的异构体），通过钯催化的分子内环闭合反应，便捷地从相应的2-芳基氨基-甲基-1, 4-苯醌（9a和9i-k）合成而成。此外，还以相同的方法合成了系列类似物，包括6-、7-和8-取代的3-甲基碳唑-1, 4-醌衍生物（1b-g）以及与1a-g对应的2-甲基碳唑醌（6a-g）。碳-13核磁共振谱的比较分析提供了对2-或3-甲基碳唑醌结构分配的有用信息。

  DOI：

  10.1248/cpb.39.328

文献信息

• Synthesis and antihypertensive activity of 6,7-disubstituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols
  作者：John M. Evans、Charles S. Fake、Thomas C. Hamilton、Robert H. Poyser、Graham A. Showell

  DOI：10.1021/jm00375a007

  日期：1984.9

  A series of novel 6,7-disubstituted trans-3,4-dihydro-2, 2-dimethyl-4-pyrrolidino-(or piperidino)-2H-1-benzopyran-3-ols was prepared and tested for antihypertensive activity in the conscious spontaneously hypertensive rat (SHR) and compared with certain of their monosubstituted analogues. The potent blood pressure lowering activity of the 6-monosubstituted compounds was enhanced by incorporation of

  制备了一系列新颖的6,7-二取代的反式3,4-二氢-2,2-二甲基-4-吡咯烷基-（或哌啶子基）-2H-1-苯并吡喃-3-醇，并在其中测试了降压活性有意识的自发性高血压大鼠（SHR），并与某些单取代类似物进行了比较。通过在C（7）处引入一个乙酰氨基或氨基，可以增强6个单取代化合物的有效降压活性，而在一个C（7）处引入一个氨基（而不是一个乙酰氨基），可以增强7-硝基取代的化合物的降血压活性。 C（6）。在反式-4-吡咯烷基-或-4-哌啶子基-2,2-二甲基-2H中6-硝基或6-氰基与7-（乙酰氨基）或7-氨基和6-氨基与7-硝基的组合-1-苯并吡喃酚在SHR中对肼屈嗪和钙拮抗剂硝苯地平具有优异的降压活性。这些化合物的合成途径涉及将2H-1-苯并吡喃转化为用吡咯烷或哌啶处理的溴代醇。当以6-氰基-7-[[（三氟乙酰基）氨基] -2,2-二甲基苯并吡喃]为起始原料时，完成了6-氰基-7-氨基类似物的制备。
• 4-Acylaminobenzopyrans useful as anti-hypertensive agents
  申请人：Beecham Group p.l.c.

  公开号：US04481214A1

  公开（公告）日：1984-11-06

  Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.2 is nitro, cyano or C.sub.1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C.sub.1-6 alkyl or by C.sub.2-7 alkanoyl; one of R.sub.3 and R.sub.4 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.3 and R.sub.4 together with the carbon atom to which they are attached are C.sub.2-5 polymethylene; either R.sub.5 is hydroxy, C.sub.1-6 alkoxy or C.sub.2-7 acyloxy and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 together are a bond; R.sub.7 is hydrogen, C.sub.1-6 alkyl optionally substituted by hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl or carboxy, or C.sub.1-2 alkyl substituted by halogen, or C.sub.2-6 alkenyl; R.sub.8 is hydrogen or C.sub.1-6 alkyl; and X is oxygen or sulphur; the R.sub.8 --N--CX--R.sub.7 group being trans to the R.sub.5 group when R.sub.5 and R.sub.6 together are not a bond; or, when one or the other of R.sub.1 and R.sub.2 is an amino or an amino-containing group, a pharmaceutically acceptable salt thereof, having anti-hypertensive activity.

  化合物的式子（I）：##STR1## 其中：R.sub.1和R.sub.2中的任意一个是氢，另一个选择自C.sub.1-6烷基羰基，C.sub.1-6烷氧羰基，C.sub.1-6烷基羰氧基，C.sub.1-6烷基羟甲基，硝基，氰基，氯基，三氟甲基，C.sub.1-6烷基磺酰基，C.sub.1-6烷基磺酰基，C.sub.1-6烷氧基磺酰基，C.sub.1-6烷氧基磺酰基，C.sub.1-6烷基羰基氨基，C.sub.1-6烷氧基羰基氨基，C.sub.1-6硫代羰基烷基，C.sub.1-6硫代羰基烷氧基，C.sub.1-6烷基硫代羰基氧基，C.sub.1-6烷基硫代甲基，甲酰基或氨基磺酰基，氨基部分可以选择性地被一个或两个C.sub.1-6烷基取代，或C.sub.1-6烷基磺酰基氨基，C.sub.1-6烷基磺酰胺基C.sub.1-6烷氧基磺酰基氨基或C.sub.1-6烷氧基磺酰胺基或以C.sub.1-6烷基羰基，硝基或氰基末端取代的乙烯基，或--C(C.sub.1-6烷基)NOH或--C(C.sub.1-6烷基)NNH.sub.2，或R.sub.1和R.sub.2中的一个是硝基，氰基或C.sub.1-3烷基羰基，另一个是甲氧基或氨基，可以选择性地被一个或两个C.sub.1-6烷基或C.sub.2-7烷酰基取代；R.sub.3和R.sub.4中的一个是氢或C.sub.1-4烷基，另一个是C.sub.1-4烷基或R.sub.3和R.sub.4与它们所连接的碳原子一起是C.sub.2-5聚亚甲基；R.sub.5是羟基，C.sub.1-6烷氧基或C.sub.2-7酰氧基，R.sub.6是氢或R.sub.5和R.sub.6一起是一个键；R.sub.7是氢，C.sub.1-6烷基，可以选择性地被羟基，C.sub.1-6烷氧基，C.sub.1-6烷氧羰基或羧基取代，或由卤素取代的C.sub.1-2烷基，或C.sub.2-6烯基；R.sub.8是氢或C.sub.1-6烷基；X是氧或硫；当R.sub.5和R.sub.6一起不是键时，R.sub.8--N--CX--R.sub.7基团与R.sub.5基团是反式的；或者，当R.sub.1和R.sub.2中的一个是氨基或含氨基的基团时，其药学上可接受的盐具有抗高血压活性。
• Benzopyrans useful for treating hypertension
  申请人：Beecham Group p.l.c.

  公开号：US04568692A1

  公开（公告）日：1986-02-04

  Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or -C(C.sub.1-6 alkyl)NOH or -C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.2 is nitro, cyano or C.sub.1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C.sub.1-6 alkyl or by C.sub.2-7 alkanoyl; one of R.sub.3 and R.sub.4 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.3 and R.sub.4 together with the carbon atom to which they are attached are C.sub.2-5 polymethylene; either R.sub.5 is hydroxy, C.sub.1-6 alkoxy or C.sub.2-7 acyloxy and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 together are a bond; R.sub.7 is hydrogen, C.sub.1-6 alkyl optionally substituted by hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl or carboxy, or C.sub.1-2 alkyl substituted by halogen, or C.sub.2-6 alkenyl; R.sub.8 is hydrogen or C.sub.1-6 alkyl; and X is oxygen or sulphur; the R.sub.8 --N--CX--R.sub.7 group being trans to the R.sub.5 group when R.sub.5 and R.sub.6 together are not a bond; or, when one or the other of R.sub.1 and R.sub.2 is an amino or an amino-containing group, a pharmaceutically acceptable salt thereof, having anti-hypertensive activity.

  式（I）的化合物：##STR1## 其中：R.sub.1和R.sub.2中的任意一个是氢，另一个选自C.sub.1-6烷基羰基，C.sub.1-6烷氧基羰基，C.sub.1-6烷基羰氧基，C.sub.1-6烷基羟甲基，硝基，氰基，氯代，三氟甲基，C.sub.1-6烷基亚磺酰基，C.sub.1-6烷基磺酰基，C.sub.1-6烷氧基亚磺酰基，C.sub.1-6烷氧基磺酰基，C.sub.1-6烷基羰基氨基，C.sub.1-6烷氧基羰基氨基，C.sub.1-6烷基硫代羰基，C.sub.1-6烷氧基硫代羰基，C.sub.1-6烷基硫代羰氧基，C.sub.1-6烷基硫甲基，甲酰基或氨基亚磺酰基，氨基磺酰基或氨基羰基，氨基基团可选择地被一个或两个C.sub.1-6烷基取代，或C.sub.1-6烷基亚磺酰氨基，C.sub.1-6烷基磺酰氨基，C.sub.1-6烷氧基亚磺酰氨基或C.sub.1-6烷氧基磺酰氨基或以C.sub.1-6烷基羰基，硝基或氰基为末端的乙烯基，或 -C（C.sub.1-6烷基）NOH或-C（C.sub.1-6烷基）NNH.sub.2中的一个为R.sub.1和R.sub.2中的一个是硝基，氰基或C.sub.1-3烷基羰基，另一个是甲氧基或氨基，可选择地被一个或两个C.sub.1-6烷基或C.sub.2-7烷酰基取代;R.sub.3和R.sub.4中的一个是氢或C.sub.1-4烷基，另一个是C.sub.1-4烷基或R.sub.3和R.sub.4与它们连接的碳原子一起是C.sub.2-5聚亚甲基; R.sub.5是羟基，C.sub.1-6烷氧基或C.sub.2-7酰氧基，R.sub.6是氢或R.sub.5和R.sub.6一起是一个键; R.sub.7是氢，可选择地被羟基，C.sub.1-6烷氧基，C.sub.1-6烷氧基羰基或羧基取代的C.sub.1-6烷基，或被卤素取代的C.sub.1-2烷基，或C.sub.2-6烯基; R.sub.8是氢或C.sub.1-6烷基; X是氧或硫; 当R.sub.5和R.sub.6一起不是键时，R.sub.8--N--CX--R.sub.7基团是与R.sub.5基团反向的; 或者，当R.sub.1和R.sub.2中的一个是氨基或含氨基的基团时，其药学上可接受的盐具有降压活性。
• Anti-hypertensive chromanol derivatives
  申请人：Beecham Group Limited

  公开号：US04366163A1

  公开（公告）日：1982-12-28

  Compounds of the formula (I) ##STR1## and salts and pro-drugs thereof, wherein: R.sub.1 is a hydrogen atom or a lower alkyl group; R.sub.2 is a hydrogen atom or a lower alkyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; R.sub.4 is a hydrogen atom or an alkyl group; R.sub.5 is a lower alkyl or a substituted alkyl group; or R.sub.4 and R.sub.5 are joined so that together with the nitrogen atom to which they are attached they form a 5-, 6- or 7-membered ring optionally containing an oxygen or sulphur atom; R.sub.6 is an electron donating group; R.sub.7 is an electron withdrawing group; and the NR.sub.4 R.sub.5 and OR.sub.3 moieties are trans having compositions containing them and processes for their preparation.

  公式(I)的化合物及其盐和前药，其中：R.sub.1是氢原子或低碳基；R.sub.2是氢原子或低碳基；R.sub.3是氢原子或低碳基；R.sub.4是氢原子或烷基；R.sub.5是低碳基或取代烷基；或R.sub.4和R.sub.5结合在一起，与它们附着的氮原子一起形成一个可选包含氧或硫原子的5、6或7元环；R.sub.6是电子供体基团；R.sub.7是电子提取基团；以及包含它们的组成物和其制备方法。
• New Carbazole Alkaloids from Murraya euchrestifolia.
  作者：Chiriro ITO、Mayumi NAKAGAWA、Tian-Shung WU、Hiroshi FURUKAWA

  DOI：10.1248/cpb.39.1668

  日期：——

  Seven new carbazole alkaloids, named pyraryafolines-B (1), -C (3), and -D (5), and euchrestines-A (7), -B (9), -C (10), and -D (11) were isolated from stem bark of Murraya euchrestifolia HAYATA (Rutaceae) collected in Taiwan and their sturctures were characterized by means of spectral methods. Pyrayafoline-B (1) was also synthesized.

  从台湾采集的芸香科植物 Murraya euchrestifolia HAYATA 的茎皮中分离出 7 种新的咔唑生物碱，分别命名为 pyraryafolines-B (1)、-C (3) 和 -D (5)，以及 euchrestines-A (7)、-B (9)、-C (10) 和 -D (11)。还合成了 Pyrayafoline-B（1）。