3-(甲基氨基)-3-氧代丙酸 | 42105-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(甲基氨基)-3-氧代丙酸
• 英文名称: 3-(methylamino)-3-oxopropanoic acid
• 英文别名: malonic acid monomethyl amide；N-Methylmalonaminsaeure；N-Methyl-malonamsaeure
• CAS: 42105-98-6
• 化学式: C₄H₇NO₃
• mdl: MFCD06208488
• 分子量: 117.104
• InChiKey: ANSCABGFLRQFHU-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  3-(甲基氨基)-3-氧代丙酸 、 (R)-N-methyl-N-(5-azaspiro[2.4]heptan-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 (R)-N-methyl-3-(7-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-5-azaspiro[2.4]heptan-5-yl)-3-oxopropanamide
  参考文献：
  名称：

  Design, synthesis and evaluation of (R)-3-(7-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-5-azaspiro[2.4]heptan-5-yl)-3-oxopropanenitrile as a JAK1-selective inhibitor

  摘要：

  我们发现了一种新的选择性JAK1抑制剂，其选择性指数为48，并确定了其在CIA和AIA模型中的有效性。

  DOI：

  10.1039/c7md00568g
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 甲胺 以 水 为溶剂， 反应 52.0h， 生成 3-(甲基氨基)-3-氧代丙酸
  参考文献：
  名称：

  Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: variable-temperature NMR and IR studies on a homologous diamide series

  摘要：

  We have studied intramolecular hydrogen bonding in a homologous series of diamides (compounds 1-6) in methylene chloride, 9:1 carbon tetrachloride/benzene, and acetonitrile. By correlating variable-temperature H-1 NMR and IR measurements, we have shown that the temperature dependence of the amide proton NMR chemical shift (DELTA-delta/DELTA-T) can provide qualitative (and in some cases quantitative) information on the thermodynamic relationship between the intramolecularly hydrogen bonded and non-hydrogen-bonded states of flexible molecules. Among the hydrogen-bonded ring sizes represented in the diamide series, the intramolecular interaction is particularly enthalpically favorable in the nine-membered hydrogen-bonded ring (compound 4). Variable-temperature IR and NMR data indicate that the internally hydrogen bonded state of diamide 4 is 1.4-1.6 kcal/mol more favorable enthalpically than the non-hydrogen-bonded state, in methylene chloride solution; the non-hydrogen-bonded state is 6.8-8.3 eu more favorable entropically in this solvent. In contrast, there appear to be much smaller enthalpy differences between the internally hydrogen bonded and non-hydrogen-bonded states of diamides 2 and 3. Our findings are important methodologically because the temperature dependences of amide proton chemical shifts are commonly used to elucidate peptide conformation in solution. Our results show that previous "rules" for the interpretation of such data are incomplete. In non-hydrogen-bonding solvents, small amide proton DELTA-delta/DELTA-T values have been taken to mean that the proton is either entirely free of hydrogen bonding or completely locked in an intramolecular hydrogen bond over the temperature range studied. We demonstrate that an amide proton can be equilibrating between intramolecularly hydrogen bonded and non-hydrogen-bonded states and still manifest a small chemical shift temperature dependence (implying that the hydrogen-bonded and non-hydrogen-bonded states are of similar enthalpy).

  DOI：

  10.1021/ja00004a016

文献信息

• 4-Tolyl-ethynyl-octahydro-indole-1-ester derivatives
  申请人：Nozulak Joachim

  公开号：US20130303538A1

  公开（公告）日：2013-11-14

  The invention relates to compounds of the formula (I) in which the substituents are as defined in the specification; in free form or in salt form; to their preparation, to their use as medicament and to medicaments comprising them.

  该发明涉及化合物(I)的公式，其中取代基如规范中所定义；以自由形式或盐形式存在；其制备方法，其用作药物以及包含它们的药物。
• 4-tolyl-ethynyl-octahydro-indole-1-ester derivatives
  申请人：Nozulak Joachim

  公开号：US09067881B2

  公开（公告）日：2015-06-30

  The invention relates to compounds of the formula (I) in which the substituents are as defined in the specification; in free form or in salt form; to their preparation, to their use as medicament and to medicaments comprising them.

  该发明涉及公式（I）中取代基的化合物，其中取代基如规范中定义的；以自由形式或盐形式存在；它们的制备，它们作为药物的用途以及包含它们的药物。
• WO2021055849A5
  申请人：——

  公开号：WO2021055849A5

  公开（公告）日：2023-09-26
• Alborz, Manoochehr; Douglas, Kenneth T.; Rullo, Gregory R., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1681 - 1688
  作者：Alborz, Manoochehr、Douglas, Kenneth T.、Rullo, Gregory R.、Yaggi, Norbert F.

  DOI：——

  日期：——
• Design, synthesis and evaluation of (<i>R</i>)-3-(7-(methyl(7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidin-4-yl)amino)-5-azaspiro[2.4]heptan-5-yl)-3-oxopropanenitrile as a JAK1-selective inhibitor
  作者：Chieyeon Chough、Sunmin Lee、Misuk Joung、Jaemin Lee、Jong Hoon Kim、B. Moon Kim

  DOI：10.1039/c7md00568g

  日期：——

  We discovered a new JAK1-selective inhibitor with a selectivity index of 48 and identified its efficacy in CIA and AIA models.

  我们发现了一种新的选择性JAK1抑制剂，其选择性指数为48，并确定了其在CIA和AIA模型中的有效性。