N-(2-bromoethyl)-2-phenoxyacetamide | 194935-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(2-bromoethyl)-2-phenoxyacetamide
• 英文别名: phenoxy-acetic acid-(2-bromo-ethylamide)；Phenoxy-essigsaeure-(2-brom-aethylamid)
• CAS: 194935-57-4
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 258.115
• InChiKey: USHYBVARLOHGKI-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  423.2±30.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-bromoethyl)-2-phenoxyacetamide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以86%的产率得到N-(2-bromoethyl)-2-phenoxyethanethioamide
  参考文献：
  名称：

  用Lawesson试剂对N-（ω-卤代烷基）取代的酰胺进行亚硫酰化：轻松合成4,5-二氢-1,3-噻唑和5,6-二氢-4 H -1,3-噻嗪

  摘要：

  的硫化和环化Ñ（ - ω -halogenoalkyl） -取代酰胺（和相关化合物）与劳森氏试剂（LR = 2,4-双（4-甲氧基苯基）-1,3,2,4-二硫2， 4-二硫化物）已被研究。用LR处理酰胺1，以中等至良好的产率得到相应的硫代酰胺2（表）。后者在用碱处理后，在单独的步骤或一锅法中得到环化的标题化合物，即4,5-二氢-1,3-噻唑3或相应的5-6-二氢-4 H-噻嗪4通过脱卤化氢反应。

  DOI：

  10.1002/hlca.200590000
• 作为产物：
  描述：

  2-溴乙胺氢溴酸盐 、 苯氧乙酰氯 生成 N-(2-bromoethyl)-2-phenoxyacetamide
  参考文献：
  名称：

  Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

  摘要：

  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.

  DOI：

  10.1021/jo970308h

文献信息

• 2-(ARYLOXYMETHYL)THIAZOLINES AND PENTHIAZOLINES
  作者：CARL DJERASSI、CAESAR R. SCHOLZ

  DOI：10.1021/jo01149a041

  日期：1950.5
• US2579478
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Thionation ofN-(?-Halogenoalkyl)-Substituted Amides withLawesson's Reagent: Facile Synthesis of 4,5-Dihydro-1,3-thiazoles and 5,6-Dihydro-4H-1,3-thiazines
  作者：Yasuhiro Kodama、Mayuko Ori、Takehiko Nishio

  DOI：10.1002/hlca.200590000

  日期：2005.2

  The thionation and cyclization of N-(ω-halogenoalkyl)-substituted amides (and related compounds) with Lawesson's reagent (LR=2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) has been investigated. Treatment of the amides 1 with LR gave the corresponding thioamides 2 in moderate to good yields (Table). The latter, upon treatment with base, afforded, either in a separate step or in

  的硫化和环化Ñ（ - ω -halogenoalkyl） -取代酰胺（和相关化合物）与劳森氏试剂（LR = 2,4-双（4-甲氧基苯基）-1,3,2,4-二硫2， 4-二硫化物）已被研究。用LR处理酰胺1，以中等至良好的产率得到相应的硫代酰胺2（表）。后者在用碱处理后，在单独的步骤或一锅法中得到环化的标题化合物，即4,5-二氢-1,3-噻唑3或相应的5-6-二氢-4 H-噻嗪4通过脱卤化氢反应。