N-(1,3-dimercaptopropan-2-yl)hexadecanamide | 1347659-66-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(1,3-dimercaptopropan-2-yl)hexadecanamide
• 英文别名: N-[1,3-bis(sulfanyl)propan-2-yl]hexadecanamide
• CAS: 1347659-66-8
• 化学式: C₁₉H₃₉NOS₂
• 分子量: 361.657
• InChiKey: BQEZGTIJIMPILN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  31.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S,S'-(2-hexadecanamidopropane-1,3-diyl)diethanethioate 在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到N-(1,3-dimercaptopropan-2-yl)hexadecanamide
  参考文献：
  名称：

  Interstaple Dithiol Cross-Linking in Au₂₅(SR)₁₈ Nanomolecules: A Combined Mass Spectrometric and Computational Study

  摘要：

  A systematic study of cross-linking chemistry of the Au-25(SR)(18) nanomolecule by dithiols of varying chain length, HS-(CH2)(n)-SH where n = 2, 3, 4, 5, and 6, is presented here. Monothiolated Au-25 has six [RSAuSRAuSR] staple motifs on its surface, and MALDI mass spectrometry data of the ligand exchanged clusters show that propane (C3) and butane (C4) dithiols have ideal chain lengths for interstaple cross-linking and that up to six C3 or C4 dithiols can be facilely exchanged onto the cluster surface. Propanedithiol predominately exchanges with two monothiols at a time, making cross-linking bridges, while butanedithiol can exchange with either one or two monothiols at a time. The extent of cross-linking can be controlled by the Au-25(SR)(18) is to dithiol ratio, the reaction time of ligand exchange, or the addition of a hydrophobic tail to the dithiol. MALDI MS suggests that during ethane (C2) dithiol exchange, two ethanedithiols become connected by a disulfide bond; this result is supported by density functional theory (DFT) prediction of the optimal chain length for the intrastaple coupling. Both optical absorption spectroscopy and DFT computations show that the electronic structure of the Au-25 nanomolecule retains its main features after exchange of up to eight monothiol ligands.

  DOI：

  10.1021/ja206436x