N-(2-甲基丙烯酰基)甘氨酸甲酯 | 31978-15-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-(2-甲基丙烯酰基)甘氨酸甲酯
• 英文名称: N-(2-methylpropenoyl)glycine methyl ester
• 英文别名: N-methacryloylglycine；methyl 2-methacrylamidoacetate；MMAA；Methacrylylglycinmethylester；methyl 2-(2-methylprop-2-enoylamino)acetate
• CAS: 31978-15-1
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: HJOVKCMUQACXBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-甲基丙烯酰基)甘氨酸甲酯 在 溴 、 sodium acetate 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 24.33h， 生成 1-methoxycarbonylmethyl-3-bromo-3-methylazetidin-2-one
  参考文献：
  名称：

  A Facile Conversion of 2-Substituted Acrylamides to 1,3-Disubstituted 3-Bromo-2-azetidinones

  摘要：

  N-Substituted 2,3-dibromo-2-alkylacrylamides obtained by the bromination of 2-alkylacrylamides were converted to 1,3-disubstituted 3-bromo-2-azetidinones in excellent yields upon treatment with potassium carbonate in acetone under refluxing.

  DOI：

  10.1080/00397919308009807
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以55%的产率得到N-(2-甲基丙烯酰基)甘氨酸甲酯
  参考文献：
  名称：

  Poly[ N ‐(2‐hydroxypropyl)methacrylamide]‐Modified Magnetic γ‐F ₂ O ₃ Nanoparticles Conjugated with Doxorubicin for Glioblastoma Treatment

  摘要：

  AbstractWith the aim to develop a new anticancer agent, we prepared poly[N‐(2‐hydroxypropyl)methacrylamide‐co‐methyl 2‐methacrylamidoacetate] [P(HP‐MMAA)], which was reacted with hydrazine to poly[N‐(2‐hydroxypropyl)methacrylamide‐co‐N‐(2‐hydrazinyl‐2‐oxoethyl)methacrylamide] [P(HP‐MAH)] to conjugate doxorubicin (Dox) via hydrazone bond. The resulting P(HP‐MAH)‐Dox conjugate was used as a coating of magnetic γ‐Fe2O3 nanoparticles obtained by the coprecipitation method. In vitro toxicity of various concentrations of Dox, P(HP‐MAH)‐Dox, and γ‐Fe2O3@P(HP‐MAH)‐Dox nanoparticles was determined on somatic healthy cells (human bone marrow stromal cells hMSC), human glioblastoma line (GaMG), and primary human glioblastoma (GBM) cells isolated from GBM patients both at a short and prolonged exposition time (up to 7 days). Due to hydrolysis of the hydrazone bond in acid milieu of tumor cells and Dox release, the γ‐Fe2O3@P(HP‐MAH)‐Dox nanoparticles significantly decreased the GaMG and GBM cell growth compared to free Dox and P(HP‐MAH)‐Dox in low concentration (10 nM), whereas in hMSCs it remained without effect. γ‐F2O3@PHP nanoparticles alone did not affect the viability of any of the tested cells.

  DOI：

  10.1002/cmdc.201900564

文献信息

• SmI₂-Promoted Radical Addition of Nitrones to α,β-Unsaturated Amides and Esters:  Synthesis of γ-Amino Acids via a Nitrogen Equivalent to the Ketyl Radical
  作者：Ditte Riber、Troels Skrydstrup

  DOI：10.1021/ol027386y

  日期：2003.1.1

  [reaction: see text] Alkyl nitrones undergo radical addition reactions to a series of alpha,beta-unsaturated amides and esters when subjected to samarium diiodide via a nitrogen equivalent to a ketyl radical anion. This reaction conveniently provides access to a variety of functionalized gamma-amino acids. The methodology was extended to the asymmetric synthesis of 4-substituted gamma-amino acids,

  [反应：见正文]当烷基氮酮经相当于酮基自由基阴离子的氮与二碘化sa反应时，烷基硝酮会与一系列α，β-不饱和酰胺和酯发生自由基加成反应。该反应方便地提供了获得各种官能化的γ-氨基酸的途径。通过将硝酮自由基加成反应与具有手性助剂的丙烯酸酯/酰胺的反应，该方法扩展到了4-取代的γ-氨基酸的不对称合成。
• Catelani, Giorgio; Nejad, Farzaneh Moftakhari Kamrani; D'Angeli, Ferruccio, Gazzetta Chimica Italiana, 1992, vol. 122, # 1, p. 51 - 54
  作者：Catelani, Giorgio、Nejad, Farzaneh Moftakhari Kamrani、D'Angeli, Ferruccio、Cavicchioni, Giorgio、Marchetti, Paolo

  DOI：——

  日期：——
• GUM BASES AND CHEWING GUMS USING THERMOSENSITIVE POLYMERS
  申请人：Wm. Wrigley Jr. Company

  公开号：EP3355706A1

  公开（公告）日：2018-08-08
• RESIN, RESIST COMPOSITION AND METHOD FOR PRODUCING RESIST PATTERN
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20160075806A1

  公开（公告）日：2016-03-17

  A resist composition includes (A1) a resin which includes a structural unit represented by formula (a4), a structural unit having a cyclic ether, and the resin has no acid-labile group, (A2) a resin having an acid-labile group, and an acid generator: wherein R 3 represents a hydrogen atom or a methyl group, and R 4 represents a C 1 to C 24 saturated hydrocarbon group having a fluorine atom and a methylene group contained in the saturated hydrocarbon group may be replaced by an oxygen atom or a carbonyl group.
• US9671691B2
  申请人：——

  公开号：US9671691B2

  公开（公告）日：2017-06-06