5-[(3-甲氧基苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮 | 213699-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-[(3-甲氧基苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮
• 中文别名: 2,2-二甲基-5-[(3-甲氧基苯基氨基)亚甲基]-1,3-二氧六环-4,6-二酮
• 英文名称: 5-(((3-methoxyphenyl)amino)methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[[(3-methoxyphenyl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-(((3-methoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-((3-methoxyphenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(3-Methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxan-4,6-dione；5-[(3-methoxyphenyl-amino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione；5-{[(3-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(3-Methoxyphenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(3-methoxyanilino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 213699-52-6
• 化学式: C₁₄H₁₅NO₅
• mdl: MFCD02936591
• 分子量: 277.277
• InChiKey: VJUROJBWDHBLOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[(3-甲氧基苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 0.41h， 生成 4-(2-Aminoethyl)amino-7-methoxyquinoline
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040
• 作为产物：
  描述：

  5-(甲氧基甲烯基)-2,2-二甲基-1,3-二氧己环-4,6-二酮 、 间氨基苯甲醚 以 乙腈 为溶剂， 反应 0.25h， 以100%的产率得到5-[(3-甲氧基苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮
  参考文献：
  名称：

  Regioselective Synthesis of Quinolin-4-ones by Pyrolysis of Anilinomethylene Derivatives of Meldrum’s Acid

  摘要：

  在闪速真空热解（FVP）条件下，梅氏酸的富电子和缺电子苯胺亚甲基衍生物通过亚胺酰基乙烯中间体环化成喹啉-4-酮的效率相同。

  DOI：

  10.1055/s-0029-1217383

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099274A1

  公开（公告）日：2003-12-04

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

  丙型肝炎病毒抑制剂公开了具有以下通式：其中R1、R2、R3、R'、B、Y和X在描述中有所描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• Gas-Phase Pyrolysis in Organic Synthesis: Rapid Green Synthesis of 4-Quinolinones
  作者：Nouria Al-Awadi、Ismail Abdelhamid、Ismail Abdelhamid、Alya Al-Etaibi、Mohamed Elngadi

  DOI：10.1055/s-2007-985573

  日期：——

  Gas-phase pyrolysis of aminomethylene Meldrum’s acid derivatives gave quinolinones and/or amines depending on the -nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate.

  根据芳基氨基部分的性质，氨基亚甲基 Meldrum 的酸衍生物的气相热解得到喹啉酮和/或胺。取代基对反应速率和热解产物性质的影响支持通过最初形成的烯酮胺中间体进行的分子内亲核取代反应。
• [EN] PROCESS FOR PREPARING SUBSTITUTED QUINOLIN-4-OL COMPOUNDS<br/>[FR] MÉTHODE DE PRÉPARATION DE COMPOSÉS DE QUINOLÉINE-4-OL SUBSTITUÉS
  申请人：CALITOR SCIENCES LLC

  公开号：WO2018026877A1

  公开（公告）日：2018-02-08

  The invention relates to a process for preparing substituted quinolin-4-ol compounds useful for preparing protein tyrosine kinase (PTK) inhibitors which are useful in treating cancer.

  本发明涉及一种制备取代喹啉-4-醇化合物的方法，该化合物用于制备蛋白酪氨酸激酶（PTK）抑制剂，该抑制剂可用于治疗癌症。
• 取代的4-羟基喹啉类化合物的制备方法
  申请人：广东东阳光药业有限公司

  公开号：CN107641099A

  公开（公告）日：2018-01-30

  本发明涉及取代的4‑羟基喹啉类化合物的制备方法，该类化合物是用于制备治疗癌症的蛋白质酪氨酸激酶(PTK)抑制剂的中间体。
• Hepatitis C virus inhibitors
  申请人：——

  公开号：US20040106559A1

  公开（公告）日：2004-06-03

  Hepatitis C virus inhibitors are disclosed having the general formula: 1 wherein R 1 , R 2 , R 3 , R′, B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  本文披露了具有以下一般式的丙型肝炎病毒抑制剂：1，其中R1、R2、R3、R'、B、Y和X在说明书中有描述。还披露了包含这些化合物的组合物和使用这些化合物抑制HCV的方法。