N-(2-hydroxyethyl)-4-biphenylylacetamide | 223531-71-3

• 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: N-(2-hydroxyethyl)-4-biphenylylacetamide
• 英文别名: biphenyl-4-yl-acetic acid-(2-hydroxy-ethylamide)；Biphenyl-4-yl-essigsaeure-(2-hydroxy-aethylamid)；N-(2-hydroxyethyl)-2-(4-phenylphenyl)acetamide
• CAS: 223531-71-3
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: CKBDLZZWFNTLNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-4-biphenylylacetamide 在 氯化亚砜 作用下， 反应 20.0h， 以60.8%的产率得到N-(2-chloroethyl)-4-biphenylylacetamide
  参考文献：
  名称：

  Ion Pair Acidities and Aggregation of Some Amide and Oxazoline Enolates in THF^,

  摘要：

  Equilibrium lithium ion pair acidities at 25 degrees C have been determined in THF for the following acetamides: N,N-dimethyl-(4-biphenylyl)acetamide (1) (19.69), N,N-diethyl-(4-biphenylyl)acetamide (2) (20.30), N,N-dimethyl-diphenylacetamide (3) (20.76), N,N-diethyl-diphenylacetamide (4) (21.99), and 1-(diphenylmethylcarbonyl)pyrrolidine (5) (21.08). These acidity data compare well with those previously reported for the corresponding cesium enolates. Lithium and cesium ion pair acidities in THF are reported for two oxazolines: 2-(4-biphenylylmethyl)oxazoline (6) (Li, 21.53; Cs, 25.49) and (E)-(4S,5R)-2-(4-biphenylylmethyl)-4-methyl-5-phenyloxazoline (7) (Li, 20.10; Cs 24.21). Studies of their acidities over a wide range of concentrations indicate that all of the lithium and cesium enolates of 1-7 are essentially monomeric at concentrations ranging from 10(-8) to 10(-4) M. Traces of dimer were detected for the lithium enolates of amides 1 and 2 and for the cesium enolate of oxazoline 6. Their dimerization constants (M-1) were found to be about 450, 200, and 150, respectively. All of the other lithium and cesium enolate probably form small amounts of dimer, but the dimerization constant of < 100 M-1 is below the limit of precision of our spectroscopic method.

  DOI：

  10.1021/jo981846c
• 作为产物：
  描述：

  4-联苯乙酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(2-hydroxyethyl)-4-biphenylylacetamide
  参考文献：
  名称：

  Ion Pair Acidities and Aggregation of Some Amide and Oxazoline Enolates in THF^,

  摘要：

  Equilibrium lithium ion pair acidities at 25 degrees C have been determined in THF for the following acetamides: N,N-dimethyl-(4-biphenylyl)acetamide (1) (19.69), N,N-diethyl-(4-biphenylyl)acetamide (2) (20.30), N,N-dimethyl-diphenylacetamide (3) (20.76), N,N-diethyl-diphenylacetamide (4) (21.99), and 1-(diphenylmethylcarbonyl)pyrrolidine (5) (21.08). These acidity data compare well with those previously reported for the corresponding cesium enolates. Lithium and cesium ion pair acidities in THF are reported for two oxazolines: 2-(4-biphenylylmethyl)oxazoline (6) (Li, 21.53; Cs, 25.49) and (E)-(4S,5R)-2-(4-biphenylylmethyl)-4-methyl-5-phenyloxazoline (7) (Li, 20.10; Cs 24.21). Studies of their acidities over a wide range of concentrations indicate that all of the lithium and cesium enolates of 1-7 are essentially monomeric at concentrations ranging from 10(-8) to 10(-4) M. Traces of dimer were detected for the lithium enolates of amides 1 and 2 and for the cesium enolate of oxazoline 6. Their dimerization constants (M-1) were found to be about 450, 200, and 150, respectively. All of the other lithium and cesium enolate probably form small amounts of dimer, but the dimerization constant of < 100 M-1 is below the limit of precision of our spectroscopic method.

  DOI：

  10.1021/jo981846c

文献信息

• Biosynthesis of Penicillins. V.¹ Substituted Phenylacetic Acid Derivatives as Penicillin Precursors
  作者：Joseph W. Corse、Reuben G. Jones、Quentin F. Soper、Calvert W. Whitehead、Otto K. Behrens

  DOI：10.1021/ja01189a001

  日期：1948.9
• Ion Pair Acidities and Aggregation of Some Amide and Oxazoline Enolates in THF^,
  作者：Antonio Facchetti、Andrew Streitwieser

  DOI：10.1021/jo981846c

  日期：1999.4.1

  Equilibrium lithium ion pair acidities at 25 degrees C have been determined in THF for the following acetamides: N,N-dimethyl-(4-biphenylyl)acetamide (1) (19.69), N,N-diethyl-(4-biphenylyl)acetamide (2) (20.30), N,N-dimethyl-diphenylacetamide (3) (20.76), N,N-diethyl-diphenylacetamide (4) (21.99), and 1-(diphenylmethylcarbonyl)pyrrolidine (5) (21.08). These acidity data compare well with those previously reported for the corresponding cesium enolates. Lithium and cesium ion pair acidities in THF are reported for two oxazolines: 2-(4-biphenylylmethyl)oxazoline (6) (Li, 21.53; Cs, 25.49) and (E)-(4S,5R)-2-(4-biphenylylmethyl)-4-methyl-5-phenyloxazoline (7) (Li, 20.10; Cs 24.21). Studies of their acidities over a wide range of concentrations indicate that all of the lithium and cesium enolates of 1-7 are essentially monomeric at concentrations ranging from 10(-8) to 10(-4) M. Traces of dimer were detected for the lithium enolates of amides 1 and 2 and for the cesium enolate of oxazoline 6. Their dimerization constants (M-1) were found to be about 450, 200, and 150, respectively. All of the other lithium and cesium enolate probably form small amounts of dimer, but the dimerization constant of < 100 M-1 is below the limit of precision of our spectroscopic method.