5-bromo-1-octanoylindoline-2,3-dione | 1453089-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-bromo-1-octanoylindoline-2,3-dione
• 英文别名: 5-bromo-1-octanoylisatine
• CAS: 1453089-89-8
• 化学式: C₁₆H₁₈BrNO₃
• 分子量: 352.228
• InChiKey: VMTMJXSLBIGRCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromo-1-octanoylindoline-2,3-dione 在 氨 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到N-(2-(2-amino-2-oxoacetyl)-4-bromophenyl)octanamide
  参考文献：
  名称：

  Chirality of the molecular assembly determined by intra-/inter-N–H⋯O hydrogen bonding in doubly substituted N-octanoylglyoxylic amides

  摘要：

  N-Octanoylglyoxylic amides have been synthesized from N-octanoylisatins and their self-assembly analyzed in the solid state by X-ray crystallography. Of the seven compounds, only two utilize intramolecular N1-H1 center dot center dot center dot O2 hydrogen bonds, whereas five of them forgo this intramolecular hydrogen bond to achieve two centrosymmetric N-H center dot center dot center dot O bonds possessing a non-planar conformation with intramolecular triple C=O center dot center dot center dot C=O dipolar contacts. These alternative conformations with resulting intermolecular interactions influence the self-assembly process distinctly; the former have molecules packed in chiral space groups whereas the latter associate in non-chiral space groups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.052
• 作为产物：
  描述：

  辛酸 在 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.25h， 生成 5-bromo-1-octanoylindoline-2,3-dione
  参考文献：
  名称：

  Chirality of the molecular assembly determined by intra-/inter-N–H⋯O hydrogen bonding in doubly substituted N-octanoylglyoxylic amides

  摘要：

  N-Octanoylglyoxylic amides have been synthesized from N-octanoylisatins and their self-assembly analyzed in the solid state by X-ray crystallography. Of the seven compounds, only two utilize intramolecular N1-H1 center dot center dot center dot O2 hydrogen bonds, whereas five of them forgo this intramolecular hydrogen bond to achieve two centrosymmetric N-H center dot center dot center dot O bonds possessing a non-planar conformation with intramolecular triple C=O center dot center dot center dot C=O dipolar contacts. These alternative conformations with resulting intermolecular interactions influence the self-assembly process distinctly; the former have molecules packed in chiral space groups whereas the latter associate in non-chiral space groups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.052