(2,5-dimethoxybenzyl)-(2,2-dimethoxyethyl)amine | 54879-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,5-dimethoxybenzyl)-(2,2-dimethoxyethyl)amine
• 英文别名: acetaldehyde dimethyl acetal；N-(2,5-dimethoxybenzyl)-2,2-dimethoxyethanamine；N-[(2,5-dimethoxyphenyl)methyl]-2,2-dimethoxyethanamine
• CAS: 54879-79-7
• 化学式: C₁₃H₂₁NO₄
• mdl: MFCD12515585
• 分子量: 255.314
• InChiKey: FMBQHYNNSVDSFH-UHFFFAOYSA-N

物化性质

• 沸点：
  155 °C(Press: 1.3 Torr)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  (2,5-dimethoxybenzyl)-(2,2-dimethoxyethyl)amine 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 硫酸 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 77.5h， 生成 7-(甲基氨基)异喹啉-5,8-二酮
  参考文献：
  名称：

  Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of Caulibugulones A–D

  摘要：

  Marine alkaloids caulibugulones A-D were synthesized in six steps starting from the readily available 2,5-dimethoxybenzaldehyde. Pomeranz-Fritsch reaction of N-(2,S-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide proceeded smoothly to give 5,8-dimethoxyisoquinoline, which was oxidized to isoquinolinadiones by a tunable oxidation reaction with N-haloimides. Therefore, NBS furnished direct conversion to the isoquinoline-5,8-dione; alternatively, N-haloimides of cyanuric acid provided both oxidation and halogenation generating 6,7-dihaloisoquinoline-5,8-diones. Aminolyses of these isoquinolinediones with methylamine or ethanolamine produced the isoquinolinedione alkaloids caulibugulones A-D in 24-57% overall yield.

  DOI：

  10.1021/jo302772t
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (2,5-dimethoxybenzyl)-(2,2-dimethoxyethyl)amine
  参考文献：
  名称：

  N-（三氟乙酰基）-4-去甲氧基柔红霉素的9-氮杂类似物的总化学合成和抗肿瘤评估。

  摘要：

  N-（三氟乙酰基）-4-脱甲氧基柔红霉素的9-氮杂类似物是由2，5-二甲氧基苯甲醛合成的。Pomeranz-Fritsch缩合反应，然后进行硼氢化物还原反应和酸催化的环化反应，平稳地生成了4-羟基-5,8-二甲氧基-1,2,3,4-四氢异喹啉。选择性的N-乙酰化和随后的邻苯二甲酸酐的Friedel-Crafts酰化反应生成2-乙酰基5,12-二羟基-1,2-二氢-2-氮杂并蒽-6,11-二酮，将其作为二甲醚进行保护并环氧化为酰化的氮杂布里格酸酐。通过脱水成4-酮基，将其转化为（+/-）-2-乙酰基-4-羟基-5,12-二甲氧基-1,2,3,4-四氢-2-氮杂并蒽-6,11-二酮。类似物，然后逐步或原位还原氰基硼氢化物。用三氯化硼除去保护基，并用旋光的N，O-双（三氟乙酰基）金葡糖胺溴化物和三氟甲磺酸银将所得的糖苷配基糖苷化。通过柱色谱分离得到的非对映异构体，并通过CD和NMR光谱确定其结构

  DOI：

  10.1021/jm00157a027

文献信息

• Synthesis of Indenoisoquinoliniums and Methods of Use
  申请人：Cushman Mark S.

  公开号：US20080242692A1

  公开（公告）日：2008-10-02

  Substituted indenoisoquinolinium compounds, and pharmaceutical formulations of substituted indenoisoquinolinium compounds are described. Also described are processes for preparing substituted indenoisoquinolinium compounds. Also described are methods for treating cancer in mammals using the described substituted indenoisoquinolinium compounds or pharmaceutical formulations thereof.

  描述了取代的茚喹啉化合物，以及取代的茚喹啉化合物的制药配方。还描述了制备取代的茚喹啉化合物的方法。还描述了使用所述的取代的茚喹啉化合物或其制药配方来治疗哺乳动物癌症的方法。
• Synthesis of indenoisoquinoliniums and methods of use
  申请人：Purdue Research Foundation

  公开号：US07781445B2

  公开（公告）日：2010-08-24

  Substituted indenoisoquinolinium compounds, and pharmaceutical formulations of substituted indenoisoquinolinium compounds are described. Also described are processes for preparing substituted indenoisoquinolinium compounds. Also described are methods for treating cancer in mammals using the described substituted indenoisoquinolinium compounds or pharmaceutical formulations thereof.

  本文介绍了替代的吲哚异喹啉化合物以及替代的吲哚异喹啉化合物的药物配方。还介绍了制备替代吲哚异喹啉化合物的方法。同时，本文还介绍了使用所述的替代吲哚异喹啉化合物或其药物配方治疗哺乳动物癌症的方法。
• Synthesis and Mechanism of Action Studies of a Series of Norindenoisoquinoline Topoisomerase I Poisons Reveal an Inhibitor with a Flipped Orientation in the Ternary DNA−Enzyme−Inhibitor Complex As Determined by X-ray Crystallographic Analysis
  作者：Alexandra Ioanoviciu、Smitha Antony、Yves Pommier、Bart L. Staker、Lance Stewart、Mark Cushman

  DOI：10.1021/jm050076b

  日期：2005.7.1

  Several norindenoisoquinolines substituted with methoxy or methylenedioxy groups have been prepared and their anticancer properties evaluated in cancer cell cultures and in topoisomerase I inhibition assays. 2,3-Dimethoxy-8,9-methylenedioxy-11H-indeno[1,2-c]isoquinoline hydrochloride (14) is a strong topoisomerase I inhibitor and also displays very high cytotoxicity in the NCI cancer cell culture screen (mean graph midpoint of 50 nM). The X-ray crystal structure of norindenoisoquinoline 14 in complex with topoisomerase I and DNA has been solved, providing insight into the structure-activity relationships within this class of new anticancer agents. The number and position of the norindenoisoquinoline substituents have a significant influence on biological activity and demonstrate that substitution on the nitrogen atom is not an absolute requirement for the antitumor effect of the indenoisoquinolines. Removal of the 11-keto group from the lead compound 1 and replacement of the N-alkyllactam with an unsubstituted pyridine ring causes the indenoisoquinoline ring system to flip over in the DNA-enzyme-inhibitor ternary complex. This allows the nitrogen atom to assume the hydrogen bond acceptor role of the 11-keto group, resulting in hydrogen bonding to Arg364.
• SYNTHESIS OF INDENOISOQUINOLINIUMS AND METHODS OF USE
  申请人：Purdue Research Foundation

  公开号：EP1735281A2

  公开（公告）日：2006-12-27
• US7781445B2
  申请人：——

  公开号：US7781445B2

  公开（公告）日：2010-08-24