N-acryloyl-N-methyl-L-alanine | 71325-61-6

• 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
• 英文名称: N-acryloyl-N-methyl-L-alanine
• 英文别名: N-(meth)acryloyl-L-alanine；(2S)-2-[methyl(prop-2-enoyl)amino]propanoic acid
• CAS: 71325-61-6
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: QDQIPLFMPSHKQL-YFKPBYRVSA-N

物化性质

• 沸点：
  344.7±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acryloyl-N-methyl-L-alanine 在 四氯化钛 作用下， 反应 65.0h， 生成 (S)-2-[((1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-methyl-amino]-propionic acid methyl ester
  参考文献：
  名称：

  Models for the use of .alpha.-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

  摘要：

  Three different models, depending on the Lewis acid used as a catalyst and the alpha-amino acid used as a chiral auxiliary, account for the diastereofacial selectivity obtained in reactions of cyclopentadiene with N-acryloyl derivatives of L-proline, L-phenylalanine, L-alanine, and N-methyl-L-alanine esters. For alpha-amino acids without an NH group and aluminum catalysts, a reactive conformer with antiplanar enoate conformation similar to those postulated for acrylates with only one center capable of coordination is proposed. These dienophiles form a chelate complex, where the acryloyl moiety is in syn conformation, with TiCl4. For alpha-amino acids with an NH group, a reactive intermediate with an antiplanar disposition in the acryloyl moiety and the conformation of the amino ester fixed by an intramolecular hydrogen bond accounts for the results with both kinds of catalyst. These models seem to have general application for the use of alpha-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions.

  DOI：

  10.1021/jo00023a020
• 作为产物：
  描述：

  N-甲基-L-丙氨酸 、 丙烯酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 以40%的产率得到N-acryloyl-N-methyl-L-alanine
  参考文献：
  名称：

  Models for the use of .alpha.-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

  摘要：

  Three different models, depending on the Lewis acid used as a catalyst and the alpha-amino acid used as a chiral auxiliary, account for the diastereofacial selectivity obtained in reactions of cyclopentadiene with N-acryloyl derivatives of L-proline, L-phenylalanine, L-alanine, and N-methyl-L-alanine esters. For alpha-amino acids without an NH group and aluminum catalysts, a reactive conformer with antiplanar enoate conformation similar to those postulated for acrylates with only one center capable of coordination is proposed. These dienophiles form a chelate complex, where the acryloyl moiety is in syn conformation, with TiCl4. For alpha-amino acids with an NH group, a reactive intermediate with an antiplanar disposition in the acryloyl moiety and the conformation of the amino ester fixed by an intramolecular hydrogen bond accounts for the results with both kinds of catalyst. These models seem to have general application for the use of alpha-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions.

  DOI：

  10.1021/jo00023a020

文献信息

• [EN] BORONIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDE BORONIQUE
  申请人：MERCK PATENT GMBH

  公开号：WO2016050358A1

  公开（公告）日：2016-04-07

  Compounds of formula (I) are inhibitors of LMP7 and can be employed, inter alia, for the treatment of an autoimmue disorder or hematological malignancies.

  式(I)的化合物是LMP7的抑制剂，可用于治疗自身免疫性疾病或血液恶性肿瘤，等等。
• Design, synthesis, and biological evaluation of novel covalent inhibitors targeting focal adhesion kinase
  作者：Tao Chen、Yan Liu、Mingsong Shi、Minghai Tang、Wenting Si、Xue Yuan、Yi Wen、Lijuan Chen

  DOI：10.1016/j.bmcl.2021.128433

  日期：2021.12

  Forty-one new focal adhesion kinase (FAK) covalent inhibitors were designed and synthesized based on FAK inhibitor TAE226. Compound 11w displayed the highest inhibition of FAK with an IC50 value of 35 nM and exhibited potent anticancer activity against Hela, HCT116 and MDA-MB-231 cell lines with IC50 values of 0.41, 0.01 and 0.11 μM respectively, compared to TAE226 (2.68, 0.64 and 4.19 μM respectively)

  基于 FAK 抑制剂 TAE226 设计和合成了 41 种新型粘着斑激酶 (FAK) 共价抑制剂。与 TAE226 相比，化合物11w对 FAK 的抑制作用最高，IC 50值为 35 nM，对 Hela、HCT116 和 MDA-MB-231 细胞系表现出有效的抗癌活性，IC 50值分别为 0.41、0.01 和 0.11 μM。分别为 2.68、0.64 和 4.19 μM）。11w还抑制HCT-116细胞的克隆形成和迁移，刺激细胞周期停滞在G 2 /M期，诱导肿瘤细胞凋亡。复合11w在对接模型中与 FAK 的 Cys427 残基形成共价键，以剂量依赖性方式抑制 FAK 和下游蛋白的自磷酸化。此外，11w显示足够的口服生物利用度为 21.02%。在 HCT116 异种移植模型中也观察到 74.20% 的肿瘤生长抑制。这些数据表明，11w是一种有前途的 FAK 共价抑制剂。
• TWO-PART EPOXY-BASED STRUCTURAL ADHESIVES
  申请人：Gorodisher Ilya

  公开号：US20110120646A1

  公开（公告）日：2011-05-26

  A two-part structural adhesive composition comprising a curable epoxy resin, an amine curing agent, a toughening agent, and a reactive liquid modifier. The structural adhesive may also include secondary curatives, initiators, reactive diluents and combinations thereof. The structural adhesives may be used to replace or augment conventional joining means such as welds or mechanical fasteners in bonding parts together.

  一种双组分结构胶黏剂组合物，包括可固化的环氧树脂、胺类固化剂、增韧剂和反应性液态改性剂。结构胶黏剂还可以包括次生固化剂、引发剂、反应性稀释剂和它们的组合。结构胶黏剂可用于取代或增强传统连接手段，如焊接或机械紧固件，将零件粘合在一起。
• REACTIVE LIQUID MODIFIERS
  申请人：Gorodisher Ilya

  公开号：US20110130518A1

  公开（公告）日：2011-06-02

  Epoxy reactive liquid modifiers include acrylate functionalized compounds, acrylamide functionalized compounds, oxalic amide functionalized compounds, actoacetoxy functionalized urethanes and acetoacetoxy functionalized polyalkenes. The reactive liquid modifiers are incorporated into epoxy resin compositions comprising a curable epoxy resin, an amine curing agent, and the reactive liquid modifier, wherein the reactive liquid modifier is polymerized to form at least one of an interpenetrating polymer network and a semi-interpenetrating polymer network with the curable epoxy resin.

  环氧树脂反应性液态改性剂包括丙烯酸酯官能化化合物、丙烯酰胺官能化化合物、草酸酰胺官能化化合物、乙酰丙酮官能化脲和乙酰丙酮官能化聚烯烃。这些反应性液态改性剂被加入到环氧树脂组合物中，包括可固化环氧树脂、胺类固化剂和反应性液态改性剂，其中反应性液态改性剂与可固化环氧树脂聚合形成至少一种交错聚合物网络或半交错聚合物网络。
• Method of preparing N-acryloyl-alpha-amino acids
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0246849A1

  公开（公告）日：1987-11-25

  A novel, one-pot procedure for the preparation of N-acryloyl-a-amino acids involves the steps of: i) reacting a ketone, an ammonium salt, and a cyanide salt in water, optionally in the presence of ammonium hydroxide and a co-solvent, to form an aminonitrile; ii) acryloylating the aminonitrile in aqueous media to afford an acrylamidonitrile; and iii) hydrolyzing with aqueous acid the acrylamidonitrile to provide the N-acryloyl-a-amino acid.

  一种制备 N-丙烯酰基-a-氨基酸的新型单锅程序包括以下步骤：i) 在水中（可选择在氢氧化铵和助溶剂存在的情况下）使酮、铵盐和氰盐反应生成氨基腈；ii) 在水介质中使氨基腈丙烯酰化，得到丙烯酰胺腈；iii) 用水性酸水解丙烯酰胺腈，得到 N-丙烯酰基-a-氨基酸。