N-(1-甲氧基-2-苯基乙基)氨基甲酸甲酯 | 136354-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(1-甲氧基-2-苯基乙基)氨基甲酸甲酯
• 英文名称: N-methoxycarbonyl-1-methoxy-2-phenylethylamine
• 英文别名: Carbamic acid, (1-methoxy-2-phenylethyl)-, methyl ester；methyl N-(1-methoxy-2-phenylethyl)carbamate
• CAS: 136354-01-3
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: HRRNJTREZHCZPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-甲氧基-2-苯基乙基)氨基甲酸甲酯 在 palladium on activated charcoal titanium(IV) isopropylate 、 sodium hydroxide 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (4S,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid dimethylamide
  参考文献：
  名称：

  Diastereoselective synthesis of 3-amino-2-hydroxyalkanoic acid derivatives

  摘要：

  Both diastereomers of 3-amino-2-hydroxyalkanoic acid derivatives were synthesized selectively by LDA-induced reaction of N-methoxycarbonyl-1-methoxyamines with O-protected N,N-dimethylglycolamides. The inversion of the diastereoselectivity was highly achieved by 1) selecting the O-protecting groups and 2) the addition of Ti(OPr-i)(4).

  DOI：

  10.1016/0040-4039(94)02369-m
• 作为产物：
  描述：

  甲醇 、 methyl N-(2-phenylethyl)carbamate 在 sodium methylate 、 sodium bromide 作用下， 以45%的产率得到N-(1-甲氧基-2-苯基乙基)氨基甲酸甲酯
  参考文献：
  名称：

  Callens, R.; Anteunis, M. J. O.; Witte, M. De, Bulletin des Societes Chimiques Belges, 1987, vol. 96, # 8, p. 619 - 622

  摘要：

  DOI：

文献信息

• Synthesis of Methyl-1-(<i>tert</i>-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann Rearrangement Utilizing Trichloroisocyanuric Acid as an Oxidant
  作者：Zackary D. Crane、Paul J. Nichols、Tarek Sammakia、Peter J. Stengel

  DOI：10.1021/jo101504e

  日期：2011.1.7

  A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.

  利用三氯异氰尿酸（TCCA）介导的霍夫曼重排来合成-1-（叔丁氧基羰基氨基）-2-乙烯基环丙烷甲酸甲酯。在该反应中可以耐受多种官能团，包括乙烯基，环丙基，吡啶基，芳基，苄基和硝基。
• A convenient method for synthesis of optically active β-hydroxyamines from primary amines through enecarbamates as key intermediates
  作者：Yoshihiro Matsumura、Takahiro Ohishi、Chihiro Sonoda、Toshihide Maki、Mitsuaki Watanabe

  DOI：10.1016/s0040-4020(97)00170-1

  日期：1997.3

  This report describes a new method to prepare optically active β-hydroxyamines starting from primary amines. The method consists of a transformation of N-methoxycarbonylated primary amines to the corresponding enecarbamates utilizing electrochemical oxidation and an asymmetric hydroboration of the enecarbamates to produce optically active β-hydroxyamines.

  该报告描述了一种从伯胺开始制备旋光性β-羟胺的新方法。该方法包括利用电化学氧化将N-甲氧基羰基化的伯胺转化成相应的烯甲酸酯，以及烯胺酸酯的不对称加氢硼化以产生光学活性的β-羟胺。
• Preparation of Acyclic<i>N</i>-Acyl-<i>N</i>,<i>O</i>-acetals by Decarboxylation of<i>N</i>-Protected α-Amino Acids and Studies of Asymmetric Amidoalkylation with Trimethylsilyl Cyanide
  作者：Kenn E. Harding、Lee T. Liu、David G. Farrar、M. Todd Coleman、Susan K. Tansey

  DOI：10.1080/00397919108021290

  日期：1991.6

  Abstract Oxidative decarboxylation of N-acyl-α-amino acids with lead tetra-acetate followed by treatment with methanol provides a facile method for preparation of acyclic N-acyl-N,O-acetals, which can be used in asymmetric α-amidoalkylation reactions using trimethylsilyl cyanide as nucleophile.

  摘要 N-酰基-α-氨基酸用四乙酸铅氧化脱羧，然后用甲醇处理为制备可用于不对称α-酰胺烷基化反应的无环N-酰基-N,O-缩醛提供了一种简便的方法。使用三甲基氰化硅烷作为亲核试剂。
• 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.