5-[(甲基氨基)甲基]-2-呋喃甲醇 | 66357-60-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-[(甲基氨基)甲基]-2-呋喃甲醇
• 中文别名: 5-甲氨基-甲基-呋喃甲醇
• 英文名称: 2-hydroxymethyl-5-(methylaminomethyl)furan
• 英文别名: N-methyl-(5-hydroxymethyl)furfurylamine；5-(methylamino)methyl-2-furanmethanol；{5-[(Methylamino)methyl]furan-2-yl}methanol；[5-(methylaminomethyl)furan-2-yl]methanol
• CAS: 66357-60-6
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: YNROOCMHXMKDGB-UHFFFAOYSA-N

物化性质

• 沸点：
  231.0±30.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  5-[(甲基氨基)甲基]-2-呋喃甲醇 在 溴 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以78%的产率得到6-hydroxymethyl-1-methylpyridinium-3-olate
  参考文献：
  名称：

  Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose

  摘要：

  Brief exposure to bromine in water-methanol at 0 OC smoothly and effectively converts furfurylamines with hydroxymethyl (5) or glucosyloxymethyl substituents (16) into the respective 6-substituted 3-pyridinols 9 and 19, whereas the N-methyl-furfurylamines 10 and 17 elaborate the N-methyl-pyridinium betaines 13 and 22. Combination of this multistep one-pot reaction with the large scale-feasible generation of hydroxymethylfurfural (4) from D-fructose and its O-glucosyl analog 15 from isomaltulose, together with their ready conversion into furfurylamines by reductive amination, opens up a preparatively satisfactory, 3-step "reaction channel" from inexpensive sugars to hydrophilic 3-pyridinols, of interest as intermediate chemicals for drugs of the pyridostigmine type and agrochemicals. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00634-6
• 作为产物：
  描述：

  5-羟甲基糠醛 在 硫酸 作用下， 以 水 为溶剂， 生成 5-[(甲基氨基)甲基]-2-呋喃甲醇
  参考文献：
  名称：

  糠醛类生物质中间体的电化学还原胺化

  摘要：

  在环境条件下，使用水作为氢源，可以完成5-羟甲基糠醛（HMF）和各种HMF衍生物的电化学还原胺化反应。

  DOI：

  10.1039/c6gc01541g

文献信息

• Aminoalkyl furan derivatives
  申请人：Allen & Hanburys Limited

  公开号：US04128658A1

  公开（公告）日：1978-12-05

  Compounds of the general formula I: ##STR1## and physiologically acceptable salts thereof and N-oxides and hydrates, in which R.sub.1 and R.sub.2 which may be the same or different represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group ##STR2## in which R.sub.4 represents hydrogen or lower alkyl or R.sub.1 and R.sub.2 may, together with the nitrogen atom to which they are attached, form a heterocyclic ring which may contain other heteroatoms selected from O and ##STR3## R.sub.3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X is --CH.sub.2 --, O or S; Y represents .dbd. S, .dbd. O, .dbd. NR.sub.5 or .dbd. CHR.sub.6 ; Alk denotes a straight or branched alkylene chain of 1 to 6 carbon atoms; R.sub.5 is H, nitro, cyano, lower alkyl, aryl, alkylsulphonyl, or arylsulphonyl; R.sub.6 represents nitro, arylsulphonyl or alkylsulphonyl; M is an integer from 2 to 4; and N is 1 or 2; or when X .dbd. S, or --CH.sub.2 --, n is zero, 1 or 2. These compounds have H.sub.2 -antagonist activity. Intermediates in the production thereof are also provided.

  通式I的化合物：##STR1##及其生理上可接受的盐和N-氧化物和水合物，其中R.sub.1和R.sub.2可以相同也可以不同，代表氢、较低的烷基、环烷基、较低的烯基、芳基烷基或被氧原子或基团##STR2##中断的较低烷基，其中R.sub.4代表氢或较低烷基或R.sub.1和R.sub.2可以与它们连接的氮原子一起形成可能包含其他杂原子O和##STR3##的杂环环，R.sub.3是氢、较低烷基、较低烯基或烷氧基烷基；X是--CH.sub.2--、O或S；Y代表.dbd. S、.dbd. O、.dbd. NR.sub.5或.dbd. CHR.sub.6；Alk表示由1到6个碳原子的直链或支链烷基链；R.sub.5是H、硝基、氰基、较低烷基、芳基、烷基磺酰基或芳基磺酰基；R.sub.6代表硝基、芳基磺酰基或烷基磺酰基；M是从2到4的整数；N是1或2；或当X.dbd.S或--CH.sub.2--时，n为零、1或2。这些化合物具有H.sub.2-拮抗活性。还提供了其生产中间体。
• Reductive Amination, Hydrogenation and Hydrodeoxygenation of 5‐Hydroxymethylfurfural using Silica‐supported Cobalt‐ Nanoparticles
  作者：Vishwas G. Chandrashekhar、Kishore Natte、Asma M. Alenad、Ahmad S. Alshammari、Carsten Kreyenschulte、Rajenahally V. Jagadeesh

  DOI：10.1002/cctc.202101234

  日期：2022.1.10

  Valorization of HMF by cobalt-nanoparticles catalyzed reductive amination, hydrogenation and hydrodeoxygenation processes produce bio-based amines and heterocycles as well as 2,5-bis(hydroxymethyl)furan, (5-methylfuran-2-yl)methanol.

  钴纳米颗粒催化还原胺化、氢化和加氢脱氧过程对 HMF的增值产生生物基胺和杂环以及 2,5-双（羟甲基）呋喃、（5-甲基呋喃-2-基）甲醇。
• ELECTROCHEMICAL REDUCTIVE AMINATION OF FURFURAL-BASED MOLECULES
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20180057949A1

  公开（公告）日：2018-03-01

  Electrochemical cells for the reductive amination of furfural-based molecules are provided. Also provided are methods of using the electrochemical cells to carry out the electrochemical reductive amination reactions. Using the cells and methods, furfural-based molecules can be converted into amines via the conversion of their formyl groups to amine groups.

  提供了用于呋喃基分子还原胺化的电化学电池。还提供了使用这些电化学电池进行电化学还原胺化反应的方法。利用这些电池和方法，可以通过将呋喃基分子的甲酰基转化为胺基将其转化为胺。
• [EN] PREPARATION OF AMINOMETHYL FURANS AND ALKOXYMETHYL FURAN DERIVATIVES FROM CARBOHYDRATES<br/>[FR] PRÉPARATION D'AMINOMÉTHYLFURANES ET DE DÉRIVÉS D'ALCOXYMÉTHYLFURANES À PARTIR DE GLUCIDES
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2012082665A1

  公开（公告）日：2012-06-21

  Described herein are single step methods of making various classes of alkylamine derivatives of furan and tetrahydrofuran by simultaneous contact of a sugar with H2, an acid catalyst and hydrogenation catalyst in the presence of an alkylamide solvent. The hydrogenation catalyst is a heterogeneous catalyst comprising a metal selected from the group consisting of Pt, Pd, and nickel. The acid catalysts may be homogeneous mineral acid or a heterogeneous acid catalyst on substrate. In a preferred practice the two catalysts are provided on a common heterogeneous bifunctional support. Using similar combinations of acid and hydrogenation catalysts, there is also described single step methods for making furandimethanol by simultaneously contacting a hexose with the two separate catalysts in the presence of H2 in an aprotic solvent, such as dimethylformamide. With the same catalyst system and similar reaction conditions, 2, 5 furan dialkylethers can also be made in a single step when the solvent includes an ROH alcohol.

  本文描述了一种单步法制备各种类别的呋喃和四氢呋喃的烷基胺衍生物的方法，即在存在烷基酰胺溶剂的情况下，将糖与H2、酸催化剂和加氢催化剂同时接触。加氢催化剂是一种杂质催化剂，包括从Pt、Pd和镍中选择的金属。酸催化剂可以是均相矿物酸或基质上的杂质酸催化剂。在首选实践中，两种催化剂被提供在共同的杂质双功能支撑上。使用类似的酸和加氢催化剂的组合，还描述了一种单步法制备呋喃二甲醇的方法，即在无水溶剂（如二甲基甲酰胺）中，在存在H2的情况下，将己糖与两种分离的催化剂同时接触。在相同的催化剂系统和类似的反应条件下，当溶剂包括ROH醇时，也可以用单步法制备2、5-呋喃双烷醚。
• N'-Derivatives of N-(2-mercapto-ethyl)-2-nitro-1,1-ethenediamine
  申请人：Allen & Hansbury, Limited

  公开号：US04169855A1

  公开（公告）日：1979-10-02

  Compounds of the general formula: ##STR1## in which R.sub.3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl. These compounds are useful in the preparation of novel aminoalkyl furan derivatives having a selective action on histamine receptors.

  一般式为##STR1##的化合物，其中R.sub.3为氢、低级烷基、低级烯基或烷氧基烷基。这些化合物在制备具有对组胺受体选择性作用的新型氨基烷基呋喃衍生物中非常有用。