N-Hexadecyl-2-chloropyridinium iodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-Hexadecyl-2-chloropyridinium iodide
• 英文别名: 2-chloro-1-hexadecylpyridin-1-ium;iodide
• 化学式: C₂₁H₃₇ClN*I
• 分子量: 465.889
• InChiKey: NNHSYWMULRDQRU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-Hexadecyl-2-pyridone 在 sodium iodide 、 三氯氧磷 作用下， 生成 N-Hexadecyl-2-chloropyridinium iodide
  参考文献：
  名称：

  Effect of micelles on cyclization reactions: the use of N-hexadecyl-2-chloropyridinium iodide as an amphiphilic carboxyl-activating agent in lactonization and lactamization

  摘要：

  Lactonization and lactamization with a novel carboxyl-activating agent, N-hexadecyl-2-chloropy-ridinium iodide (C(16)PyCl,I), were investigated. The organization of this agent in micelles in the reaction medium facilitates cyclization giving rise to a micellar effect. Under these conditions, the corresponding lactam is produced from the omega-amino acid 12-aminododecanoic acid in good yield (double that obtained-with the Mukaiyama reagent, N-methyl-2-chloropyridinium iodide C(1)PyCl,I). On the other hand, the yield of lactone from 16-hydroxyhexadecanoic acid was the same with either carboxyl-activating agent. These results were accounted for in terms of substrate-dependent micellar effects. Because of solubility effects, the omega-amino acids and omega-hydroxy acids are not localized in comparable ways vis a vis the interface and, thus, have different reactivities. Moreover, hydrolysis of the reagents, C(16)PyCl,I and C(1)PyCl,I, was also detected. The interference of this reaction with the cyclization process was also found to depend on a micellar effect with C(16)PyCl,I that is not observed with C(1)PyCl,I.

  DOI：

  10.1021/jo00081a022
• 作为试剂：
  描述：

  16-羟基棕榈酸 在 三乙胺 、 N-Hexadecyl-2-chloropyridinium iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 氧杂环十七烷-2-酮
  参考文献：
  名称：

  Effect of micelles on cyclization reactions: the use of N-hexadecyl-2-chloropyridinium iodide as an amphiphilic carboxyl-activating agent in lactonization and lactamization

  摘要：

  Lactonization and lactamization with a novel carboxyl-activating agent, N-hexadecyl-2-chloropy-ridinium iodide (C(16)PyCl,I), were investigated. The organization of this agent in micelles in the reaction medium facilitates cyclization giving rise to a micellar effect. Under these conditions, the corresponding lactam is produced from the omega-amino acid 12-aminododecanoic acid in good yield (double that obtained-with the Mukaiyama reagent, N-methyl-2-chloropyridinium iodide C(1)PyCl,I). On the other hand, the yield of lactone from 16-hydroxyhexadecanoic acid was the same with either carboxyl-activating agent. These results were accounted for in terms of substrate-dependent micellar effects. Because of solubility effects, the omega-amino acids and omega-hydroxy acids are not localized in comparable ways vis a vis the interface and, thus, have different reactivities. Moreover, hydrolysis of the reagents, C(16)PyCl,I and C(1)PyCl,I, was also detected. The interference of this reaction with the cyclization process was also found to depend on a micellar effect with C(16)PyCl,I that is not observed with C(1)PyCl,I.

  DOI：

  10.1021/jo00081a022

文献信息

• Effect of micelles on cyclization reactions: the use of N-hexadecyl-2-chloropyridinium iodide as an amphiphilic carboxyl-activating agent in lactonization and lactamization
  作者：I. Rico、K. Halvorsen、C. Dubrule、A. Lattes

  DOI：10.1021/jo00081a022

  日期：1994.1

  Lactonization and lactamization with a novel carboxyl-activating agent, N-hexadecyl-2-chloropy-ridinium iodide (C(16)PyCl,I), were investigated. The organization of this agent in micelles in the reaction medium facilitates cyclization giving rise to a micellar effect. Under these conditions, the corresponding lactam is produced from the omega-amino acid 12-aminododecanoic acid in good yield (double that obtained-with the Mukaiyama reagent, N-methyl-2-chloropyridinium iodide C(1)PyCl,I). On the other hand, the yield of lactone from 16-hydroxyhexadecanoic acid was the same with either carboxyl-activating agent. These results were accounted for in terms of substrate-dependent micellar effects. Because of solubility effects, the omega-amino acids and omega-hydroxy acids are not localized in comparable ways vis a vis the interface and, thus, have different reactivities. Moreover, hydrolysis of the reagents, C(16)PyCl,I and C(1)PyCl,I, was also detected. The interference of this reaction with the cyclization process was also found to depend on a micellar effect with C(16)PyCl,I that is not observed with C(1)PyCl,I.