xanthobilirubinic acid n-decyl ester | 138202-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: xanthobilirubinic acid n-decyl ester
• CAS: 138202-56-9
• 化学式: C₂₇H₄₂N₂O₃
• 分子量: 442.642
• InChiKey: DKJCLEPDADSSEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  癸醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到xanthobilirubinic acid n-decyl ester
  参考文献：
  名称：

  Polymer bound pyrrole compounds, VII: Xanthobilirubinic acid esters and amides from an insoluble, polystyrene-supported precursor

  摘要：

  A series of xanthobilirubinic acid (XBR) esters (i.e., 1 c to 1 p) and amides (2 a - 2 c) have been prepared by a procedure involving detachment of the chromophore previously ester-bound to a functionalized, insoluble polystyrene (1 b). Detachment is achieved by treatment with the respective alcohol in aqueous alkali or with the amines, yielding directly the corresponding esters or amides. With primary, short-chained alcohols the ester yields are high (60% for n-C4H9-OH to 99% for C2H5-OH), but decrease rapidly with chain length (40% for n-C10H21-OH and 0% for n-C16H33-OH). The same trends are observed with the amines. These results are interpreted in terms of an (increasingly) unfavourable entropic interaction between the polymer matrix to which the chromophore is bound and the (growing) alcohol chain. The impairment by the long chained nucleophile to reach the transesterification center could also contribute, and, for the most lipophylic alcohols, their low solubility in aqueous alkali is an additional drawback. With secondary and tertiary alcohols, no ester is obtained, in agreement with a B(AC)2 mechanism involving a tetrahedral intermediate.

  DOI：

  10.1007/bf00811466