2-氨基-4-戊烯酸盐酸盐 | 108412-04-0

• 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: 2-氨基-4-戊烯酸盐酸盐
• 中文别名: DL-烯丙基甘氨酸
• 英文名称: 2RS-2-aminopent-4-enoic acid
• 英文别名: allylglycine hydrochloride；α-allylglycine hydrochloride；(+/-)-2-amino-4-pentenoic acid ; hydrochloride；(+/-)-2-Amino-4-pentensaeure; Hydrochlorid；2-Aminopent-4-enoic acid hydrochloride；2-aminopent-4-enoic acid;hydrochloride
• CAS: 108412-04-0；144073-09-6
• 化学式: C₅H₉NO₂*ClH
• 分子量: 151.593
• InChiKey: DIDZZOWASZMNQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2922499990
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  2-氨基-4-戊烯酸盐酸盐 、 氯甲酸苄酯 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 以93%的产率得到2-(((benzyloxy)carbonyl)amino)pent-4-enoic acid
  参考文献：
  名称：

  Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids

  摘要：

  Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to alpha-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H). Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100%). The solvent used for the reaction is critical. Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems). The scope of the reaction includes alpha-substituted alpha-allylglycine and derivatives as well as beta-substituted beta-allyl-beta-ammo alcohols. In the case of optically active alpha-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H. The products are easily optically enriched by crystallization. Addition of sulfur-based radicals to alpha-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.

  DOI：

  10.1021/jo00049a041
• 作为产物：
  描述：

  2-((二苯基亚甲基)氨基)戊-4-烯腈 在 盐酸 作用下， 生成 2-氨基-4-戊烯酸盐酸盐
  参考文献：
  名称：

  Synthesis of δ--α-aminoadipoyl--cysteinyl--allylglycine, and eight deuterated analogues, substrates for the investigation of the mechanism of action of isopenicillin n synthase.

  摘要：

  The synthesis of delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine (1a) from its component amino acids is described, along with the synthesis of eight analogues (1b-i) specifically deuterated at C-3 and/or C-5 of the allylglycine residue.

  DOI：

  10.1016/s0040-4020(01)91015-4

文献信息

• Preparation of Chiral Amino Esters by Asymmetric Phase-Transfer Catalyzed Alkylations of Schiff Bases in a Ball Mill
  作者：Pierrick Nun、Violaine Pérez、Monique Calmès、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/chem.201102885

  日期：2012.3.19

  The asymmetric alkylation of Schiff bases under basic conditions in a ball mill was performed. The starting Schiff bases of glycine were prepared beforehand by milling protected glycine hydrochloride and benzophenone imine, in the absence of solvent. The Schiff base was then reacted with a halogenated derivative in a ball mill in the presence of KOH. By adding a chiral ammonium salt derived from cinchonidine

  在球磨机中在碱性条件下进行席夫碱的不对称烷基化。甘氨酸的起始席夫碱是通过在没有溶剂的情况下将受保护的甘氨酸盐酸盐和二苯甲酮亚胺研磨而制备的。然后在KOH存在下，在球磨机中使席夫碱与卤代衍生物反应。通过添加衍生自辛可尼定的手性铵盐，该反应在相转移催化条件下不对称进行，获得了出色的收率，对映体过量高达75％。因为使用了等摩尔量的原料，所以大大简化了纯化。
• Vinyl-glycyl-amino-beta-lactam derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0209237A2

  公开（公告）日：1987-01-21

  β-Lactam antibiotics are disclosed having the partial structure: where R1 is: in which R2, R3 and R4 are the same or different and each is hydrogen; halogen; optionally substituted C1-6 alkyl; optionally substituted C3-7 cycloalkyl; optionally substituted C2-6 alkenyl; optionally substituted C2-6 alkynyl; amido; cyano; carboxy; formyl; C1-6 alkoxycarbonyl; mono- or di-(C1-6)alkylamido; C1-6 alkylcarbonyl; an aryl group; a heterocyclyl group; or R3 and R4 are joined together to form the residue of a carbocyclic ring having a total of from 3 to 7 carbon atoms in the ring; or R3 and R4 are joined together to form the residue of a heterocyclic ring in which R3 and R4 together may be represented by the formula -(CH2)mX(CN2)n in which X is oxygen, sulphur or a group NR5 wherein R5 is hydrogen, acyl, an amino-protecting group, or C1-6 alkyl, m is 1 to 3 and n is 1 to 3; and also the use thereof. Processes for the preparation of the compounds are disclosed together with intermediates for use therein.

  β-内酰胺类抗生素具有以下部分结构： 其中R1为 其中R2、R3和R4相同或不同，且各自为氢；卤素；任选取代的C1-6烷基；任选取代的C3-7环烷基；任选取代的C2-6烯基；任选取代的C2-6炔基；氨基；氰基；羧基；甲酰基；C1-6烷氧基羰基；单-或 二-(C1-6)烷基氨基；C1-6 烷基羰基；芳基；杂环基；或 R3 和 R4 连接在一起形成碳环的残基，环中共有 3 至 7 个碳原子；或 R3 和 R4 连接在一起形成杂环的残基，其中 R3 和 R4 可由式-(CH2)mX(CN2)n 表示，式中 X 是氧、硫或基团 NR5，其中 R5 是氢、酰基、氨基保护基团或 C1-6 烷基，m 是 1 至 3，n 是 1 至 3；以及其用途。 公开了这些化合物的制备工艺及其使用的中间体。
• A catalytic asymmetric synthesis of 5,5-dimethylproline
  作者：Jomana Elaridi、W. Roy Jackson、Andrea J. Robinson

  DOI：10.1016/j.tetasy.2005.05.003

  日期：2005.6

  The methyl ester derivative of commercially available N-acetyl-allylglycine readily undergoes cross-metathesis with 2-methylbut-2-ene and ruthenium-alkylidene catalyst to afford the prenylglycine derivative. Acid-catalysed cyclisation then affords 5,5-dimethylproline in near quantitative yield and enantioselectivity. (c) 2005 Published by Elsevier Ltd.
• Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids
  作者：Quirinus B. Broxterman、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1021/jo00049a041

  日期：1992.11

  Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to alpha-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H). Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100%). The solvent used for the reaction is critical. Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems). The scope of the reaction includes alpha-substituted alpha-allylglycine and derivatives as well as beta-substituted beta-allyl-beta-ammo alcohols. In the case of optically active alpha-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H. The products are easily optically enriched by crystallization. Addition of sulfur-based radicals to alpha-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.
• Synthesis of δ--α-aminoadipoyl--cysteinyl--allylglycine, and eight deuterated analogues, substrates for the investigation of the mechanism of action of isopenicillin n synthase.
  作者：Jack E. Baldwin、Mark Bradley、Nicholas J. Turner、Robert M. Adlington、Andrew R. Pitt、Helen Sheridan

  DOI：10.1016/s0040-4020(01)91015-4

  日期：1991.9

  The synthesis of delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine (1a) from its component amino acids is described, along with the synthesis of eight analogues (1b-i) specifically deuterated at C-3 and/or C-5 of the allylglycine residue.