2-amino-5,5-dimethyl-4,5-dihydro-4-furanone | 120533-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-amino-5,5-dimethyl-4,5-dihydro-4-furanone
• 英文别名: 5-Amino-2,2-dimethyl-2,3-dihydro-3-furanone；5-amino-2,3-dihydro-2,2-dimethyl-3-furanone；5-amino-2,3-dihydro-2,2-dimethylfuran-3-one；5-amino-2,2-dimethyl-3(2H)-furanone；5-amino-2,2-dimethylfuran-3-one
• CAS: 120533-52-0
• 化学式: C₆H₉NO₂
• mdl: MFCD02824397
• 分子量: 127.143
• InChiKey: UHRVKZXYMVCQAO-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C
• 沸点：
  194.1±40.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-(2-hydroxyethylthio)-3-methyl-1-butene-1-carbonitrile 在 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以58.2%的产率得到2-amino-5,5-dimethyl-4,5-dihydro-4-furanone
  参考文献：
  名称：

  Skvortsov, Yu. M.; Moshchevitina, E. I.; Mal'kina, A. G., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 6.1, p. 1055 - 1058

  摘要：

  DOI：

文献信息

• Synthesis of New Amino Acids with a 5-Imino-2,5-dihydro-3-furanyl Substituent­ at the Amino Group
  作者：Boris Trofimov、Anastasiya Mal’kina、Olesya Shemyakina、Angela Borisova、Valentina Nosyreva、Oleg Dyachenko、Olga Kazheva、Gennadii Alexandrov

  DOI：10.1055/s-2007-983819

  日期：2007.9

  Amino acids (glycine, β-alanine, γ-aminobutyric and ε-aminocapronic acids, d,l-valine, and d,l-leucine) react under biomimetic conditions (H2O, NaOH, pH ˜8.6-9.9, room temperature) smoothly with α,β-acetylenic γ-hydroxyacid nitriles to give a novel family of unnatural amino acids containing a 5-imino-2,5-dihydro-3-furanyl substituent at the amino group, in 61-98% yield. As follows from a single-crystal X-ray analysis of 2-[(5-imino-2,2-dimethyl-2,5-dihydro-3-furanyl)amino]acetic acid, the synthesized amino acids are zwitterions with a protonated imino group in the iminodihydrofuran moiety.

  氨基酸（甘氨酸、β-丙氨酸、γ-氨基丁酸、ε-氨基己酸、d,l-缬氨酸和d,l-亮氨酸）在仿生条件下（H2O、NaOH、pH ≈8.6-9.9、室温）平稳地与α,β-炔基γ-羟基酸腈反应，以61-98%的产率生成一类含有氨基的5-亚胺基-2,5-二氢-3-呋喃基取代基的新型非天然氨基酸。从2-[(5-亚胺基-2,2-二甲基-2,5-二氢-3-呋喃基)氨基]乙酸的单晶X射线分析可以看出，合成的氨基酸是含有亚胺双氢呋喃部分质子化亚胺基的偶极离子。
• Reactions of aminobenzoic acids with α,β-acetylenic γ-hydroxy nitriles: synthesis of functionalized amino acids and unusually facile esterification and acetylene hydration
  作者：Boris A. Trofimov、Anastasiya G. Mal'kina、Olesya A. Shemyakina、Valentina V. Nosyreva、Angela P. Borisova、Alexander I. Albanov、Olga N. Kazheva、Grigorii G. Alexandrov、Anatolii N. Chekhlov、Oleg A. Dyachenko

  DOI：10.1016/j.tet.2009.01.073

  日期：2009.3

  1 reacts with α,β-acetylenic γ-hydroxy nitriles 4 and 5 to afford 2-[(5-iminio-2,2-dialkyl-2,5-dihydro-3-furanyl)amino]benzenecarboxylates 7 and 8 (yield 73–74%), a new class of unnatural amino acids in a peculiar zwitterionic form, having the positive charge transferred to the remote imino group of the dihydrofuranyl substituent. 3- and 4-Aminobenzoic acids 2 and 3 with α,β-acetylenic γ-hydroxy nitriles

  2-氨基苯甲酸1与α，β-炔属γ-羟基腈4和5反应，得到2-[（5-亚氨基-2-2,2-二烷基-2,5-二氢-3-呋喃基）氨基]苯甲酸7和8（收率73-74％）是一类新型的两性离子形式的非天然氨基酸，其正电荷转移到二氢呋喃基取代基的远端亚氨基上。3-和4-氨基苯甲酸2和3与α，β-γ炔羟基腈4 - 6进行完全不同的变换提供cyanomethylhydroxyalkyl酮的酯9 - 12，这是由于羟基官能团的酯化反应异常容易，同时三键同时水合造成的。发现4-氨基苯甲酸3是一种将α，β-炔属γ-羟基腈4一锅转化为5-氨基-2,2-二甲基-3（2 H）-呋喃酮13的活性有机催化剂，收率为80％。
• Transformations of cyanoacetylenic alcohols in the presence of the cyanide ion
  作者：Anastasiya G. Mal’kina、Olesya A. Shemyakina、Valentina V. Nosyreva、Alexander I. Albanov、Ludmila V. Klyba、Elena R. Zhanchipova、Boris A. Trofimov

  DOI：10.1070/mc2006v016n04abeh002250

  日期：2006.1

  The transformation of 4-hydroxy-4-methylpent-2-ynenitrile in the presence of KCN in methanol (20-25 degrees C, 1 h) leads to (Z)-2-(1-hydroxy-1-methyl)but-2-enedinitrile, 4-hydroxy-3-methoxy-4-alkylalk-2-enenitrile and 2-imino-5,5-dimethyl-4-methoxycarbimide-2,5-dihydrofuran. In dioxane at room temperature, KCN catalyses the auto-transformation of cyanoacetylene to 2,2-dimethyl-3,4-di(cyanomethylene)oxetane and 2,5-di(cyanomethylene)-3,3,6,6-tetramethyl-1,4-dioxane; in aqueous dioxane (20-25 degrees C, 4 h), the reaction affords 5-amino-2,2-dimethyl-3(2H)-furanone.
• Chemo-, regio- and stereospecific addition of adenine and 8-azaadenine to α,β-acetylenic γ-hydroxy nitriles: a short-cut to novel acyclic adenosine analogues
  作者：Boris A. Trofimov、Anastasiya G. Mal'kina、Valentina V. Nosyreva、Olesya A. Shemyakina、Angela P. Borisova、Lyudmila I. Larina、Olga N. Kazheva、Grigorii G. Alexandrov、Oleg A. Dyachenko

  DOI：10.1016/j.tet.2010.01.015

  日期：2010.2

  Adenine (9H-purin-6-amine) adds readily to available alpha,beta-acetylenic gamma-hydroxy nitriles under mild conditions (molar ratio 1 1, K2CO3, DMF, rt, 10 min) to afford chemo-, regio- and stereospecifically (Z)-3-(6-amino-9H-purin-9-yl)-4-hydroxy-4-alkyl-2-alkenenitriles novel functionalized acyclic nucleoside analogues (95-98% yield) Under similar conditions (K2CO3, DMF, rt, 1 h), 8-azaadenine (3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine) reacts with 4-hydroxy-4-methyl-2-pentynenitrile nonselectively at the 7-, 8- and 9-positions to give the corresponding adducts in a 1 10 5 9 ratio, the total yield being 81% Chemo-, regio- and stereospecific addiction of 8-azaadenine to the above alpha,beta,-acetylenic gamma-hydroxy nitriles leading to (Z)-3-(7-amino-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-4-hydroxy-4-alkyl-2-alkenenitriles in 44-90% yield is attained when the reaction is carried Out without solvent in the presence Of Et3N (30 mol%), the molar ratio of 8-azaadenine alpha,beta-acetylenic nitriles being 1 2 0 (rt, 12-38 h) (C) 2010 Elsevier Ltd All rights reserved
• Synthesis and x-ray structural analysis of 2-amino-4-cyanomethylene-5,5-dimethylthiazoline
  作者：N. D. Abramova、L. V. Andriyankova、A. G. Mal'kin�、V. K. Bel'skii、�. I. Kositsyna、Yu. M. Skvortsov

  DOI：10.1007/bf00962131

  日期：1989.10