N-(2-羟基-2-苯基乙基)氨基甲酸乙酯 | 109355-73-9

• 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-(2-羟基-2-苯基乙基)氨基甲酸乙酯
• 英文名称: ethyl 2-hydroxy-2-phenylethylcarbamate
• 英文别名: (β-hydroxy-phenethyl)-carbamic acid ethyl ester；(β-Hydroxy-phenaethyl)-carbamidsaeure-aethylester；β-Carbaethoxyamino-α-phenyl-aethylalkohol；Carbaethoxyaminomethyl-phenyl-carbinol；Carbamic acid, (2-hydroxy-2-phenylethyl)-, ethyl ester；ethyl N-(2-hydroxy-2-phenylethyl)carbamate
• CAS: 109355-73-9
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: QXOFNLAUYSWAST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-羟基-2-苯基乙基)氨基甲酸乙酯 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (R)-α-(氨基甲基)苄醇
  参考文献：
  名称：

  Baker’s Yeast Reduction ofα-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols

  摘要：

  使用发酵的面包酵母对α-酰氨基苯乙酮进行酶促还原，得到了光学活性的(R)-2-酰氨基-1-芳基乙醇。进一步地，使用醋酸乙烯酯作为酰基供体，通过脂肪酶催化的拆分反应，生成了(S)-1-乙酰氧基-2-酰氨基-1-芳基乙醇和(R)-2-酰氨基-1-芳基乙醇。

  DOI：

  10.1246/bcsj.66.1216
• 作为产物：
  描述：

  扁桃腈 在 sodium amalgam 、 sodium carbonate 作用下， 生成 N-(2-羟基-2-苯基乙基)氨基甲酸乙酯
  参考文献：
  名称：

  Hess; Uibrig, Chemische Berichte, 1915, vol. 48, p. 1977

  摘要：

  DOI：

文献信息

• Osmium-Catalyzed Vicinal Oxyamination of Alkenes by <i>N</i>-(4-Toluenesulfonyloxy)carbamates
  作者：Masruri、Anthony C. Willis、Malcolm D. McLeod

  DOI：10.1021/jo301372y

  日期：2012.10.5

  N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yields and afford high regioselectivity for unsymmetrically substituted alkenes.

  在一系列单，二和三取代烯烃的分子间催化的氧化胺化反应中，基于一系列常见胺保护基的N-（4-甲苯磺酰氧基）氨基甲酸酯用作预制的氮源。该反应以低的催化剂负载量和良好的收率进行，并且对于不对称取代的烯烃提供高的区域选择性。
• Process and intermediates for beta-lactam antibiotics
  申请人：THE PRESIDENT AND FELLOWS OF HARVARD COLLEGE

  公开号：EP0362902A2

  公开（公告）日：1990-04-11

  Intermediate compounds of formula (I) wherein Ar is phenyl, C₁-C₄ alkylphenyl, halophenyl, C₁-C₄ alkoxyphenyl, naphthyl, thienyl, furyl, benzo­thienyl, or benzofuryl; R is phenyl, C₁-C₄ alkylphenyl, C₁-C₄ alkoxyphenyl, or halophenyl; Y is -CH=CH-, or -CH₂-CH₂-; and R′ is phenyl, C₁-C₄ alkylphenyl, C₁-C₄ alkoxyphenyl, halophenyl, furyl or naphthyl. Also compounds of formula (II) wherein Ar is phenyl, C₁-C₄ alkylphenyl, halophenyl, C₁-C₄ alkoxyphenyl, naphthyl, thienyl, furyl, benzo­thienyl, or benzofuryl; and R₃ is hydroxy, C₁-C₄ alkoxy, chloro, bromo, trifluoroacetoxy, or -O-P(=O)X₂ wherein X is chloro or bromo, and compounds of formula (III) wherein Ar is phenyl, C₁-C₄ alkylphenyl, halophenyl, C₁-C₄ alkoxyphenyl, naphthyl, thienyl, furyl, benzo­thienyl, or benzofuryl; R is phenyl, C₁-C₄ alkylphenyl, C₁-C₄ alkoxyphenyl, or halophenyl; and R₄ is formyl, carboxy, C₁-C₄ alkoxycarbonyl, methyl, halomethyl or hydroxymethyl, and when R₄ is other than formyl the 4-position epimers thereof.

  式 (I) 的中间体化合物 其中 Ar 是苯基、C₁-C₄ 烷基苯基、卤代苯基、C₁-C₄ 烷氧基苯基、萘基、噻吩基、呋喃基、苯并噻吩基或苯并呋喃基；R是苯基、C₁-C₄烷基苯基、C₁-C₄烷氧基苯基或卤代苯基；Y是-CH＝CH-或-CH₂-CH₂-；R′是苯基、C₁-C₄烷基苯基、C₁-C₄烷氧基苯基、卤代苯基、呋喃基或萘基。 还有式 (II) 的化合物 其中 Ar 是苯基、C₁-C₄ 烷基苯基、卤代苯基、C₁-C₄ 烷氧基苯基、萘基、噻吩基、呋喃基、苯并噻吩基或苯并呋喃基；和 R₃ 是羟基、C₁-C₄ 烷氧基、氯代、溴代、三氟乙酰氧基或 -O-P(=O)X₂ 其中 X 是氯代或溴代、 以及式 (III) 的化合物 其中 Ar 是苯基、C₁-C₄ 烷基苯基、卤代苯基、C₁-C₄ 烷氧基苯基、萘基、噻吩基、呋喃基、苯并噻吩基或苯并呋喃基；R 是苯基、C₁-C₄ 烷基苯基、C₁-C₄ 烷氧基苯基或卤代苯基；R₄ 是甲酰基、羧基、C₁-C₄ 烷氧基羰基、甲基、卤代甲基或羟甲基，当 R₄ 不是甲酰基时，是其 4 位表聚物。
• Mieczkowski, Jozef B., Bulletin of the Polish Academy of Sciences: Chemistry, 1986, vol. 34, # 3-4, p. 109 - 113
  作者：Mieczkowski, Jozef B.

  DOI：——

  日期：——
• Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates
  作者：Maria Antonietta Casadei、Franco Micheletti Moracci、Giovanni Zappia、Achille Inesi、Leucio Rossi

  DOI：10.1021/jo970308h

  日期：1997.10.1

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.
• Slotta; Heller, Chemische Berichte, 1930, vol. 63, p. 1024,1028
  作者：Slotta、Heller

  DOI：——

  日期：——