monomethylethanolaminopropionitrile | 34508-82-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: monomethylethanolaminopropionitrile
• 英文别名: MEAPN；N-(2-hydroxy-ethyl)-N-methyl-β-alanine nitrile；N-(2-Hydroxy-aethyl)-N-methyl-β-alanin-nitril；3-(N-Methyl-2-hydroxy-ethylamino)-propionsaeurenitril；2-<(2-Cyanoethyl)-methylamino>-ethanol；N-<2-Cyanethyl>-N-methyl-ethanolamin；2-Cyanoethyl-2-hydroxyethylmethylamine；3-[2-hydroxyethyl(methyl)amino]propanenitrile
• CAS: 34508-82-2
• 化学式: C₆H₁₂N₂O
• mdl: MFCD11147855
• 分子量: 128.174
• InChiKey: JHGANGDIYRLEJL-UHFFFAOYSA-N

物化性质

• 沸点：
  149-150 °C
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  monomethylethanolaminopropionitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-[3-[(2-Methoxyacridin-9-yl)amino]propyl-methylamino]ethanol
  参考文献：
  名称：

  Synthesis and DNA-sequence selectivity of a series of mono- and difunctional 9-aminoacridine nitrogen mustards

  摘要：

  The aim of this work was to identify nitrogen mustards that would react selectively with DNA, particularly in G-rich regions. A sei ies of mono- and difunctional nitrogen mustards was synthesized in which the (2-chloroethyl)amino functions were connected to the N-9 of 9-aminoacridine by way of a spacer chain consisting of two to six methylene units. The length of the spacer chain connecting the alkylating and putative DNA-intercalating groups was found to affect the preference for the alkylation of different guanine-N-7 positions in a DNA sequence. All of the compounds reacted preferentially at G's that are followed by G as do most other types of nitrogen mustards, but the degree of selectivity was greater. The compounds reacted at much lower concentrations than were required for comparable reaction by mechlorethamine (HN2), consistent with initial noncovalent binding to DNA prior to guanine-N-7 alkylation. The degree of DNA-sequence selectivity increased as the spacer-chain length decreased below four methylene units. Most strikingly, long spacer compounds reacted strongly at 5'-GT-3' sequences, Whereas this reaction was almost completely suppressed when-the spacer length was reduced to two or three methylenes. Mono- and difunctional compounds of a given spacer length showed no consistent difference in DNA-sequence preference.

  DOI：

  10.1021/jm00027a008
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 、 3-溴丙腈 反应 0.5h， 生成 monomethylethanolaminopropionitrile
  参考文献：
  名称：

  Synthesis and DNA-sequence selectivity of a series of mono- and difunctional 9-aminoacridine nitrogen mustards

  摘要：

  The aim of this work was to identify nitrogen mustards that would react selectively with DNA, particularly in G-rich regions. A sei ies of mono- and difunctional nitrogen mustards was synthesized in which the (2-chloroethyl)amino functions were connected to the N-9 of 9-aminoacridine by way of a spacer chain consisting of two to six methylene units. The length of the spacer chain connecting the alkylating and putative DNA-intercalating groups was found to affect the preference for the alkylation of different guanine-N-7 positions in a DNA sequence. All of the compounds reacted preferentially at G's that are followed by G as do most other types of nitrogen mustards, but the degree of selectivity was greater. The compounds reacted at much lower concentrations than were required for comparable reaction by mechlorethamine (HN2), consistent with initial noncovalent binding to DNA prior to guanine-N-7 alkylation. The degree of DNA-sequence selectivity increased as the spacer-chain length decreased below four methylene units. Most strikingly, long spacer compounds reacted strongly at 5'-GT-3' sequences, Whereas this reaction was almost completely suppressed when-the spacer length was reduced to two or three methylenes. Mono- and difunctional compounds of a given spacer length showed no consistent difference in DNA-sequence preference.

  DOI：

  10.1021/jm00027a008

文献信息

• [EN] PROCESS FOR THE PRODUCTION OF AMINOPROPYLMETHYLETHANOLAMINE<br/>[FR] PROCÉDÉ DE PRODUCTION D'AMINOPROPYLMÉTHYLÉTHANOLAMINE
  申请人：RHODIA OPERATIONS

  公开号：WO2013117013A1

  公开（公告）日：2013-08-15

  A new process for the production of APMMEA (aminopropylmethylethanolamine) is proposed. This process comprises at least 2 steps in which MEAPN (monomethylethanolaminopropionitrile) is first produced from MMEA (monomethylethanol amine) and ACN (acrylonitrile) and then said MEAPN is hydrogenated to obtain the corresponding amine, the APMMEA compound. APMMEA may be then eventually purified by several known process, notably by distillation.

  提出了一种生产APMMEA（氨丙基甲基乙醇胺）的新工艺。该工艺包括至少两个步骤，首先从MMEA（单甲基乙醇胺）和ACN（丙烯腈）制备MEAPN（单甲基乙醇胺丙腈），然后将所述MEAPN加氢以获得相应的胺，即APMMEA化合物。 APMMEA最终可以通过多种已知工艺进行纯化，尤其是通过蒸馏。
• Biodegradable amidoaminoesters
  申请人：Sherex Chemical Co., Inc.

  公开号：US05734069A1

  公开（公告）日：1998-03-31

  Compounds of the formula R--\x9bC(O)O(CH.sub.2).sub.1-5 !.sub.0-1 --C(O)NH(CH.sub.2).sub.2-5 --N(R.sup.2)--(CH.sub.2).sub.2-5 --OC(O)R.sup.1 wherein R and R.sup.1 are each C.sub.8 -C.sub.22 alkyl or alkenyl and R.sup.2 is C.sub.1 -C.sub.3 alkyl or hydroxyalkyl, benzyl, or --C.sub.2 H.sub.4 OC(O)R.sup.4 wherein R.sup.4 is C.sub.8 -C.sub.22 alkyl or alkenyl, and acid salts and derivatives of such compounds quaternized with methyl, ethyl or benzyl, exhibit useful fabric softening and static reduction properties, as well as biodegradability.

  式为R--\x9bC(O)O(CH.sub.2).sub.1-5 !.sub.0-1 --C(O)NH(CH.sub.2).sub.2-5 --N(R.sup.2)--(CH.sub.2).sub.2-5 --OC(O)R.sup.1的化合物中，R和R.sup.1均为C.sub.8-C.sub.22烷基或烯基，R.sup.2为C.sub.1-C.sub.3烷基或羟基烷基，苯甲基或--C.sub.2H.sub.4OC(O)R.sup.4，其中R.sup.4为C.sub.8-C.sub.22烷基或烯基，以及这些化合物的酸盐和衍生物，用甲基、乙基或苯甲基季铵化的，具有有用的柔软和静电减少性能，以及生物降解性。
• SOFTENER COMPOSITION
  申请人：Kao Corporation

  公开号：EP2372017A1

  公开（公告）日：2011-10-05

  The present invention provides a softener composition containing a specific bis(polyalkoxyalkanol) type quaternary ammonium salt represented by formula (I): [wherein R1 and R2 may be the same as or different from each other and represent a hydrocarbon group having 11 to 23 carbon atoms, R3 and R4 may be the same as or different from each other and represent a hydrocarbon group having 1 to 4 carbon atoms which may have a hydroxyl group, k and 1 may be the same as or different from each other and represent an integer of 5 to 10 and X- represents an anion.]

  本发明提供了一种柔软剂组合物，其中含有由式（I）表示的特定双（聚烷氧基烷醇）型季铵盐： [其中 R1 和 R2 可以相同或互不相同，代表具有 11 至 23 个碳原子的烃基；R3 和 R4 可以相同或互不相同，代表具有 1 至 4 个碳原子的烃基，其中可能含有羟基；k 和 1 可以相同或互不相同，代表 5 至 10 的整数；X- 代表阴离子。］
• Bodnaryuk,F.N.; Korshunov,M.A., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 2210 - 2213
  作者：Bodnaryuk,F.N.、Korshunov,M.A.

  DOI：——

  日期：——
• Sawatari,K., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 996 - 999
  作者：Sawatari,K.

  DOI：——

  日期：——