methyl 3-((methoxycarbonyl)amino)-3-methylpropanoate | 116173-78-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-((methoxycarbonyl)amino)-3-methylpropanoate
• 英文别名: methyl ((methoxycarbonyl)amino)-3-methyl propanoate；Methyl 3-(methoxycarbonylamino)butanoate
• CAS: 116173-78-5；116173-72-9
• 化学式: C₇H₁₃NO₄
• mdl: MFCD24389381
• 分子量: 175.185
• InChiKey: SQEMIAJIDMEGQR-UHFFFAOYSA-N

物化性质

• 沸点：
  266.3±23.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-((methoxycarbonyl)amino)-3-methylpropanoate 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 生成 (R)-3-氨基丁醇
  参考文献：
  名称：

  New synthesis of β-amino acids by nucleophilic addition of enolate anions to N-methoxycarbonylimines generated from α-methoxy carbamates1

  摘要：

  DOI：

  10.1016/s0040-4039(00)80062-3
• 作为产物：
  描述：

  乙酸甲酯 、 (1-methoxy-ethyl)-carbamic acid methyl ester 在 三异丙氧基氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.0h， 以70%的产率得到methyl 3-((methoxycarbonyl)amino)-3-methylpropanoate
  参考文献：
  名称：

  New synthesis of β-amino acids by nucleophilic addition of enolate anions to N-methoxycarbonylimines generated from α-methoxy carbamates1

  摘要：

  DOI：

  10.1016/s0040-4039(00)80062-3

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。
• PROCESSES FOR PRODUCING MALEAMIC ACID, ESTER THEREOF AND MALEIMIDE
  申请人：NIPPON SHOKUBAI CO., LTD.

  公开号：EP0672650A1

  公开（公告）日：1995-09-20

  A process for producing an N-unsubstituted maleimide by imidating an N-unsubstituted maleamic ester through elimination of alcohol molecule and ring closure, wherein use is made of an acidic catalyst or mono(cyclo)alkyl sulfate and it is preferable to lower the alcohol concentration in the reaction mixture. When maleamic acid is reacted with an alcohol by using an inert solvent and an acidic catalyst, a mixture of maleamic with an acidic catalyst, or a mono(cyclo)alkyl sulfate, a corresponding maleamic ester is obtained. Maleamic acid is produced by the reaction of maleic anhydride with ammonia in an inert solvent, which reaction is conducted by feeding a solution of maleic anhydride in an inert solvent into a reactor and feeding ammonia gas into an open space of the reactor to cause the ammonia to be absorbed in the solution via the surface of contact of the solution with the gas.

  一种通过消除醇分子和闭环将 N-未取代马来酰胺酯酰亚胺化而生产 N-未取代马来酰亚胺的工艺，其中使用了酸性催化剂或单（环）烷基硫酸盐，并且最好降低反应混合物中的醇浓度。当使用惰性溶剂和酸性催化剂、马来酰胺与酸性催化剂的混合物或单（环）烷基硫酸盐使马来酰胺酸与醇反应时，可得到相应的马来酰胺酯。马来酰胺酸是通过马来酸酐与氨在惰性溶剂中的反应生成的，该反应是通过将马来酸酐在惰性溶剂中的溶液注入反应器，并将氨气注入反应器的开放空间，使氨通过溶液与气体的接触面被溶液吸收而进行的。
• Reaction of N-acyl-α-methoxyamines with organozinc reagents. A convenient method for the synthesis of homoallylamines and β-amino esters
  作者：Naoki Kise、Hiroki Yamazaki、Toshirou Mabuchi、Tatsuya Shono

  DOI：10.1016/s0040-4039(00)76758-x

  日期：1994.3

  The reaction of N-acyl-alpha-methoxyamines with allyl-, propargyl-, and benzylzinc bromides and Reformatsky reagents proceeds in THF at room temperature. Homoallyl- and homopropargylamines and beta-amino esters are synthesized in good yields.
• 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.