N-acetyl-S-{N-[4-(methylthio)butyl]thiocarbamoyl}-L-cysteine

• 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-{N-[4-(methylthio)butyl]thiocarbamoyl}-L-cysteine
• 化学式: C₁₁H₂₀N₂O₃S₃
• 分子量: 324.489
• InChiKey: NSSSLRDQSNRIQU-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.43
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-(4-甲硫基-丁基)邻苯二甲酰亚胺 在 盐酸 、 sodium hydroxide 、 碳酸氢钠 、 一水合肼 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 N-acetyl-S-{N-[4-(methylthio)butyl]thiocarbamoyl}-L-cysteine
  参考文献：
  名称：

  Synthesis of isothiocyanate-derived mercapturic acids

  摘要：

  Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00141-7

文献信息

• Synthesis of isothiocyanate-derived mercapturic acids
  作者：Martijn Vermeulen、Binne Zwanenburg、Gordon J.F Chittenden、Hans Verhagen

  DOI：10.1016/s0223-5234(03)00141-7

  日期：2003.7

  Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.