(S)-2-(hexadecylamino)propan-1-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(hexadecylamino)propan-1-ol
• 英文别名: (2S)-2-(hexadecylamino)propan-1-ol
• 化学式: C₁₉H₄₁NO
• 分子量: 299.541
• InChiKey: QQPHNNWYIXKLRV-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(hexadecylamino)propan-1-ol 在 咪唑 、 氯化亚砜 、 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 (S)-3-hexadecyl-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  氨基酸衍生的离子液晶

  摘要：

  合成了新型的手性氨基酸衍生的离子型液晶，其胺和酰胺部分作为咪唑鎓头基和烷基链之间的间隔基。合成中的关键步骤利用了相对罕见的SO 3微波辅助反应中的离去基团。介晶的介晶性质是通过差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射确定的。所有液晶盐均表现出具有强相互指状的双层结构的近晶A中间相几何形状。立体生成中心的空间体积的增加阻碍了中间相的形成。在苯丙氨酸衍生的衍生物的情况下，与其他氨基酸衍生物相比，烷基链较短的同构行为被观察到，表明苯基部分具有额外的稳定作用。

  DOI：

  10.1002/chem.201302319
• 作为产物：
  描述：

  十六醛 在 sodium tetrahydroborate 作用下， 以 乙醇 、 苯 为溶剂， 反应 15.0h， 生成 (S)-2-(hexadecylamino)propan-1-ol
  参考文献：
  名称：

  Chiral Lipophilic Ligands. 1. Enantioselective Cleavage of .alpha.-Amino Acid Esters in Metallomicellar Aggregates

  摘要：

  Several chiral ligands (1a,b, 2a-d), their marked lipophilic structure featuring a binding subunit comprising a 2-substituted pyridine, a tertiary amine, and a hydroxyl, have been synthesized and their complexes with Cu(II), Zn(II), or Co(II) ions investigated in homomicellar or comicellar aggregates as enantioselective catalysts of the cleavage of p-nitrophenyl esters of alpha-amino acids (Phe, Phg, Leu). Rate accelerations up to 3 orders of magnitude over the Cu(II) catalyzed hydrolysis and enantioselectivities ranging from; 3.2 to 11.6 have been observed. In each case explored, the chiral ligand reacts faster with the enantiomeric substrate of opposite absolute configuration. Several pieces of evidence indicate that the effective cleavage process in micellar aggregates involves the following: (a) the formation of a ternary (ligand-metal ion-substrate) complex; (b) within such a complex, a nucleophilic attack of the ligand hydroxyl on the substrate to give a transacylation intermediate; and (c) the metal ion promoted hydrolysis of the transacylation intermediate with a relatively fast turnover of the catalyst. Such a mode of action does not operate outside or in the absence of micellar aggregates: in this case; the hydroxyl is displaced by water that acts as the nucleophile ina slower (less enantioselective) process. The enantioselectivity of the transacylation process appears to be little affected by the steric interaction between the substituents at the chiral center of the amino acid ester and of the ligand. We suggest that the enantioselectivity arises from a different hydration, due to steric reasons, of the diastereomeric complexes comprising the two enantiomers of the substrate. As a consequence, the relevance of the competing mechanisms of cleavage of the ester, the first one, faster, involving the hydroxyl and the second one, slower, involving a Cu(II)-bound water molecule, may be different. In the case of the less hydrated, more hydrophobic R-S or S-R complex the former, faster, mode of cleavage may be more relevant than in the case of the more hydrated, less hydrophobic, S-S or R-R complex.

  DOI：

  10.1021/jo00094a034

文献信息

• Chiral Lipophilic Ligands. 1. Enantioselective Cleavage of .alpha.-Amino Acid Esters in Metallomicellar Aggregates
  作者：Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo00094a034

  日期：1994.7

  Several chiral ligands (1a,b, 2a-d), their marked lipophilic structure featuring a binding subunit comprising a 2-substituted pyridine, a tertiary amine, and a hydroxyl, have been synthesized and their complexes with Cu(II), Zn(II), or Co(II) ions investigated in homomicellar or comicellar aggregates as enantioselective catalysts of the cleavage of p-nitrophenyl esters of alpha-amino acids (Phe, Phg, Leu). Rate accelerations up to 3 orders of magnitude over the Cu(II) catalyzed hydrolysis and enantioselectivities ranging from; 3.2 to 11.6 have been observed. In each case explored, the chiral ligand reacts faster with the enantiomeric substrate of opposite absolute configuration. Several pieces of evidence indicate that the effective cleavage process in micellar aggregates involves the following: (a) the formation of a ternary (ligand-metal ion-substrate) complex; (b) within such a complex, a nucleophilic attack of the ligand hydroxyl on the substrate to give a transacylation intermediate; and (c) the metal ion promoted hydrolysis of the transacylation intermediate with a relatively fast turnover of the catalyst. Such a mode of action does not operate outside or in the absence of micellar aggregates: in this case; the hydroxyl is displaced by water that acts as the nucleophile ina slower (less enantioselective) process. The enantioselectivity of the transacylation process appears to be little affected by the steric interaction between the substituents at the chiral center of the amino acid ester and of the ligand. We suggest that the enantioselectivity arises from a different hydration, due to steric reasons, of the diastereomeric complexes comprising the two enantiomers of the substrate. As a consequence, the relevance of the competing mechanisms of cleavage of the ester, the first one, faster, involving the hydroxyl and the second one, slower, involving a Cu(II)-bound water molecule, may be different. In the case of the less hydrated, more hydrophobic R-S or S-R complex the former, faster, mode of cleavage may be more relevant than in the case of the more hydrated, less hydrophobic, S-S or R-R complex.
• Ionic Liquid Crystals Derived from Amino Acids
  作者：Markus Mansueto、Wolfgang Frey、Sabine Laschat

  DOI：10.1002/chem.201302319

  日期：2013.11.18

  Novel chiral amino acid derived ionic liquid crystals with amine and amide moieties as spacers between the imidazolium head group and the alkyl chain were synthesised. The key step in the synthesis utilised the relatively uncommon SO3 leaving group in a microwave‐assisted reaction. The mesomorphic properties of the mesogens were determined by differential scanning calorimetry (DSC), polarising optical

  合成了新型的手性氨基酸衍生的离子型液晶，其胺和酰胺部分作为咪唑鎓头基和烷基链之间的间隔基。合成中的关键步骤利用了相对罕见的SO 3微波辅助反应中的离去基团。介晶的介晶性质是通过差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射确定的。所有液晶盐均表现出具有强相互指状的双层结构的近晶A中间相几何形状。立体生成中心的空间体积的增加阻碍了中间相的形成。在苯丙氨酸衍生的衍生物的情况下，与其他氨基酸衍生物相比，烷基链较短的同构行为被观察到，表明苯基部分具有额外的稳定作用。