methyl 3-benzyl-3-((methoxycarbonyl)amino)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-benzyl-3-((methoxycarbonyl)amino)propanoate
• 英文别名: methyl 3-benzyl-((methoxycarbonyl)amino)propanoate；Methyl 3-(methoxycarbonylamino)-4-phenylbutanoate
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: NIWKJYJAGZWNKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸甲酯 、 N-(1-甲氧基-2-苯基乙基)氨基甲酸甲酯 在 三异丙氧基氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到methyl 3-benzyl-3-((methoxycarbonyl)amino)propanoate
  参考文献：
  名称：

  A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of N-Alkoxycarbonyl-1-methoxyamines with Esters

  摘要：

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.

  DOI：

  10.1021/jo990821q

文献信息

• Hofmann-Type Rearrangement of Imides by in Situ Generation of Imide-Hypervalent Iodines(III) from Iodoarenes
  作者：Katsuhiko Moriyama、Kazuma Ishida、Hideo Togo

  DOI：10.1021/ol300028j

  日期：2012.2.3

  The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted

  使用由PhI，m -CPBA和TsOH·H 2 O原位生成的高价碘（III）试剂对芳族和脂族酰亚胺进行霍夫曼型重排，可在醇中存在碱的情况下进行，以提供邻氨基苯甲酸衍生物和氨基酸衍生物分别高收率。这通过经由醇解之后是霍夫曼一个串联反应反应进行重排由酰亚胺-λ的形成促进了3 -iodane中间。
• Effect of catalytic alkali metal bromide on Hofmann-type rearrangement of imides
  作者：Katsuhiko Moriyama、Kazuma Ishida、Hideo Togo

  DOI：10.1039/c2cc33914e

  日期：——

  The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.

  使用KBr作为催化剂的芳族和脂族酰亚胺的霍夫曼型重排进行以提供芳族和脂族氨基酸衍生物。我们还开发了这种方法合成加巴喷丁的新合成途径。
• Inhibition of human leukocyte elastase by derivatives of N-hydroxysuccinimide. A structure-activity-relationship study
  作者：W. C. Groutas、M. J. Brubaker、M. A. Stanga、J. C. Castrisos、J. P. Crowley、E. J. Schatz

  DOI：10.1021/jm00127a034

  日期：1989.7

  A series of compounds derived from 3-alkyl-N-hydroxysuccinimide have been synthesized and their inhibitory activity toward human leukocyte elastase has been investigated. Compounds having an isobutyl or isopropyl group at the C-3 position have been found to be particularly effective inactivators of the enzyme. The introduction of a trans-styryl group (as in compounds 16 and 18) results in a drastic

  已经合成了一系列衍生自3-烷基-N-羟基琥珀酰亚胺的化合物，并且已经研究了它们对人白细胞弹性蛋白酶的抑制活性。已经发现在C-3位具有异丁基或异丙基的化合物是该酶特别有效的灭活剂。反式-苯乙烯基的引入（如化合物16和18中的）导致抑制活性的急剧增强，表明苯环和酶的S2'亚位点之间有利的相互作用。发现该化合物在缓冲溶液中高度稳定，在17小时（观察期）后结构完整性没有明显变化。对模型化合物和高场NMR的研究表明，这些化合物可作为酶的基于机理的抑制剂。
• A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of <i>N</i>-Alkoxycarbonyl-1-methoxyamines with Esters
  作者：Naoki Kise、Nasuo Ueda

  DOI：10.1021/jo990821q

  日期：1999.10.1

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.