N-acetyl-S-(4-coumarinyl)-L-cysteine | 135505-66-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-S-(4-coumarinyl)-L-cysteine
• 英文别名: (2R)-2-acetamido-3-(2-oxochromen-4-yl)sulfanylpropanoic acid
• CAS: 135505-66-7
• 化学式: C₁₄H₁₃NO₅S
• 分子量: 307.327
• InChiKey: JFSQBPXKAHKUSF-JTQLQIEISA-N

物化性质

• 熔点：
  215-220 °C
• 沸点：
  632.5±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-acetyl-S-(4-coumarinyl)-L-cysteine 在 三氟化硼 作用下， 以82%的产率得到N-acetyl-S-(4-coumarinyl)-L-cysteine methyl ester
  参考文献：
  名称：

  Synthesis of N-acetyl-S-(3-coumarinyl)-cysteine methyl ester and HPLC analysis of urinary coumarin metabolites

  摘要：

  N-Acetyl-S-(3-coumarinyl)cysteine, a metabolite of coumarin in rodents, has been synthesized as methyl ester. A new synthetic route to prepare N-acetyl-S-(3-coumarinyl)-D,L-cysteine methyl ester (1) comprises reaction of 3-mercaptocoumarin (3) with N-acetyl-3-chloro-D,L-alanine methyl ester (4). N-acetyl-S-(4-coumarinyl)-L-cysteine (10) was obtained by reaction of 3-bromocoumarin (12) and N-acetyl-L-cysteine (13). A method for the determination of N-acetyl-S-(3-coumarinyl)cysteine as its methyl ester in urine by HPLC has been developed. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0300-483x(03)00204-x
• 作为产物：
  描述：

  香豆素 在 溴 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.0h， 生成 N-acetyl-S-(4-coumarinyl)-L-cysteine
  参考文献：
  名称：

  Synthesis of N-acetyl-S-(3-coumarinyl)-cysteine methyl ester and HPLC analysis of urinary coumarin metabolites

  摘要：

  N-Acetyl-S-(3-coumarinyl)cysteine, a metabolite of coumarin in rodents, has been synthesized as methyl ester. A new synthetic route to prepare N-acetyl-S-(3-coumarinyl)-D,L-cysteine methyl ester (1) comprises reaction of 3-mercaptocoumarin (3) with N-acetyl-3-chloro-D,L-alanine methyl ester (4). N-acetyl-S-(4-coumarinyl)-L-cysteine (10) was obtained by reaction of 3-bromocoumarin (12) and N-acetyl-L-cysteine (13). A method for the determination of N-acetyl-S-(3-coumarinyl)cysteine as its methyl ester in urine by HPLC has been developed. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0300-483x(03)00204-x

文献信息

• Synthesis of N-acetyl-S-(3-coumarinyl)-cysteine methyl ester and HPLC analysis of urinary coumarin metabolites
  作者：Gerhard Eisenbrand、Michael Otteneder、Weici Tang

  DOI：10.1016/s0300-483x(03)00204-x

  日期：2003.8

  N-Acetyl-S-(3-coumarinyl)cysteine, a metabolite of coumarin in rodents, has been synthesized as methyl ester. A new synthetic route to prepare N-acetyl-S-(3-coumarinyl)-D,L-cysteine methyl ester (1) comprises reaction of 3-mercaptocoumarin (3) with N-acetyl-3-chloro-D,L-alanine methyl ester (4). N-acetyl-S-(4-coumarinyl)-L-cysteine (10) was obtained by reaction of 3-bromocoumarin (12) and N-acetyl-L-cysteine (13). A method for the determination of N-acetyl-S-(3-coumarinyl)cysteine as its methyl ester in urine by HPLC has been developed. (C) 2003 Elsevier Ireland Ltd. All rights reserved.