3-(dimethylaminomethylene)-4-chromanone | 74396-87-5

• 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: 3-(dimethylaminomethylene)-4-chromanone
• 英文别名: 3-(dimethylamino)methylenechroman-4-one；3-(Dimethylaminomethylene)-chroman-4-one；3-(dimethylaminomethylidene)chromen-4-one
• CAS: 74396-87-5
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: GMSGZAPXOBAWPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethylaminomethylene)-4-chromanone 在 sodium acetate 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-Methylsulfinyl-5H-[1]benzopyrano[4,3-d]pyrimidine
  参考文献：
  名称：

  Antiinflammatory agents: new series of N-substituted amino acids with complex pyrimidine structures endowed with antiphlogistic activity

  摘要：

  A series of N-methyl-N-pyrimidin-2-yl glycines 2a-e, having the pyrimidine ring fused with a cyclohexane [N-methyl-N-(5,6,7,8-tetrahydroquinazolin-2-yl)glycine], cyclohexene [N-methyl-N-(5,6-dihydroquinazolin-2-yl)glycine], 1,2,3,4-tetrahydronaphthalene [N-methyl-N-(5,6-dihydrobenzo[e]quinazolin-2-yl)glycine], benzopyrane [N-methyl-N-(5-phenyl-5H-[1]benzopyrano[4,3-d]pyrimidin-2-yl)glyci ne] and benzothiopyrane [N-methyl-N-(5H-[1]benzothiopyrano[4,3-d]pyrimidin-2-yl)glycine] ring, was prepared and tested for antiinflammatory activity. With the same purpose a number of N-5H-[1]benzopyrano[4,3-d]pyrimidin-2-yl substituted amino acids 3a-e, having a different chain length and branching were also synthesized and tested. All the described products 2 and 3 showed an appreciable antiphlogistic activity, particularly 2b and 2c.

  DOI：

  10.1016/s0014-827x(98)00109-8
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以13.6 g的产率得到3-(dimethylaminomethylene)-4-chromanone
  参考文献：
  名称：

  一种具有抗氧化作用的苯并吡喃类化妆品辅料及其制备方法

  摘要：

  本发明公开了一种具有抗氧化作用的苯并吡喃类化妆品辅料及其制备方法，属于功能有机分子的合成技术领域。本发明的技术方案要点为：该苯并吡喃类化妆品辅料具有结构本发明通过一种新的方法合成了一种结构新颖的苯并呋喃类化合物，并且进行了抗氧化研究，并且进行了人体皮肤斑贴实验，显示在一定浓度下对人体皮肤没有不良影响，进而希望能够应用到化妆品中，作为抗氧化添加剂辅料。

  公开号：

  CN109879882A

文献信息

• 一种具有清除自由基效果的苯并吡喃类化妆 品辅料及其制备方法
  申请人：浙江瑀美生物科技有限公司

  公开号：CN109912611B

  公开（公告）日：2021-07-20

  本发明公开了一种具有清除自由基效果的苯并吡喃类化妆品辅料及其制备方法，属于功能有机分子的合成技术领域。本发明的技术方案要点为：该苯并吡喃类化妆品辅料具有结构本发明通过一种新的方法合成了一种结构新颖的苯并呋喃类化合物，并且进行了抗氧化研究，并且进行了人体皮肤斑贴实验，显示在一定浓度下对人体皮肤没有不良影响，进而希望能够应用到化妆品中，作为抗氧化添加剂辅料。
• Fused polycyclic 2-aminopyrimidine derivatives
  申请人：Celltech R & D Limited

  公开号：US06599908B1

  公开（公告）日：2003-07-29

  Fused polycyclic 2-aminopyrimidines of formula (1): wherein Ar is an optionally substituted aromatic or heteroaromatic group; X is a carbon or nitrogen atom; Y is a carbon or nitrogen atom; Z is a linker group; A together with X and Y forms an optionally substituted monocyclic or bicyclic aromatic or heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof are described. The compounds are potent and selective inhibitors of the protein tyrosine kinases p56lck and p59fyn and are of use in the prophylaxis and treatment of immune diseases, hyperproliferative disorders and other diseases in which inappropriate p56lck and/or p59fyn activity is believed to have a role.

  化合物的化学式为（1）：其中，Ar为可选取代的芳香或杂芳基；X为碳或氮原子；Y为碳或氮原子；Z为连接基；A与X和Y一起形成可选取代的单环或双环芳香或杂芳基；以及其盐、溶剂化物、水合物和N-氧化物。这些化合物是蛋白酪氨酸激酶p56lck和p59fyn的有效选择性抑制剂，并可用于预防和治疗免疫疾病、高增殖性疾病和其他与不适当的p56lck和/或p59fyn活性有关的疾病。
• Reaction of ketenes with<i>N,N</i>-disubstituted à-aminomethyleneketones. IX. Synthesis of 2<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>][1]benzopyran derivatives
  作者：Luisa Mosti、Pietro Schenone、Giulia Menozzi

  DOI：10.1002/jhet.5570170112

  日期：1980.1

  3-dichloro-3,4-dihydro-5H-pyrano[3,2-c][1]benzopyran-2-ones only in the case of aromatic N-substitution. Dehydrochlorination with triethylamine of these adducts afforded N,N-disubstituted 4-amino-3-chloro-5H-pyrano[3,2-c][1]benzopyran-2-ones in good to moderate yield. The cycloaddition to 3-dimethylaminomethylene-4-chromanone led directly to 3-chloro-4-dimethylamino-5H-pyrano[3,2-c][1]benzopyran-2-one.

  将二氯乙烯酮环加成到N，N-二取代的3-氨基亚甲基-4-发色酮上，得到高收率的N，N-二取代的4-氨基-3，3-二氯-3，4-二氢-5 H-吡喃并[3,2- c ] [1]苯并吡喃-2-酮仅在芳族N-取代的情况下。这些加合物用三乙胺脱氯化氢可得到良好产率的N，N-二取代的4-氨基-3-氯-5 H-吡喃并[3，2- c ] [1]苯并吡喃-2-酮。环加成到3-甲基氨基亚甲基-4-苯并二氢吡喃直接导致3-氯-4-二甲氨基-5- ħ吡喃并[3,2- c ^ ] [1]苯并吡喃-2-酮。
• New polycyclic pyrimidine derivatives with antiplatelet in vitro activity: synthesis and pharmacological screening
  作者：Olga Bruno、Silvia Schenone、Angelo Ranise、Francesco Bondavalli、Elisabetta Barocelli、Vigilio Ballabeni、Milena Chiavarini、Simona Bertoni、Massimiliano Tognolini、Mariannina Impicciatore

  DOI：10.1016/s0968-0896(00)00272-8

  日期：2001.3

  The preparation and the pharmacological screening of novel anti-aggregatory/antiphlogistic polycyclic pyrimidine derivatives are described. The compounds were developed starting from bioactive 2-aminobenzopyranopyrimidine derivatives in order to assess the importance of the benzopyrano[4,3-d]pyrimidine structure and the role of an amino basic moiety in position 2. Antiplatelet activity was assessed in vitro against ADP and arachidonic acid-induced aggregation in guinea-pig plasma. Anti-inflammatory analgesic/antipyretic activities were studied in rat paw oedema, mouse writhing test and E coli-induced rat fever. Ulcerogenic and gastroprotective effects were also investigated in vivo on rat gastric mucosa. Among the tested compounds, the 5-substituted benzopyranopyrimidine derivatives 3d and 4d proved to be the most active antiplatelet agents as potent as acetylsalicylic acid against arachidonic acid-stimulated aggregation. Furthermore the 2-methylthio derivative 4d was endowed with greater efficacy against ADP aggregation suggesting that additional non-TXA(2) dependent mechanisms are involved in its biological activity. Orally administered at 100 mg kg(-1) in rats this latter compound displayed antiphlogistic acitivity comparable to indomethacin (10 mg kg(-1)) coupled with an unusual gastroprotective effect on ethanol-induced ulcers. In conclusion, these findings indicate that the 5-pyrrolidino-2-methylthiobenzopyrano[4d] fulfils the chemical requirements to exhibit antiplatelet activity associated with gastroprotective effect. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Bruno; Schenone; Ranise, Il Farmaco, 1996, vol. 51, # 2, p. 137 - 140
  作者：Bruno、Schenone、Ranise、Bondavalli、D'Amico、Filippelli、Berrino、Rossi

  DOI：——

  日期：——