(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)heptanedioic acid | 1350450-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)heptanedioic acid
• 英文别名: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)heptanedioic acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)heptanedioic acid
• CAS: 1350450-51-9
• 化学式: C₂₂H₂₃NO₆
• 分子量: 397.428
• InChiKey: WNGQUSSMDLUWLH-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  十二烷基伯胺 、 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)heptanedioic acid 在 哌啶 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (S)-2-amino-N1,N7-didodecylheptanediamide
  参考文献：
  名称：

  Controlling the Position of Functional Groups at the Liquid/Solid Interface: Impact of Molecular Symmetry and Chirality

  摘要：

  With the aim of controlling the position of functional groups in a substrate-supported monolayer, a new family of functionalized linear alkyl chains was designed and synthesized, aided by molecular mechanics and dynamics simulations of its two-dimensional self-assembly on graphite. The self-assembly of these amino functionalized diamides at the liquid/solid interface was investigated with scanning tunneling microscopy. Intermolecular hydrogen-bonding interactions involving amides, combined with the effect of molecular symmetry and chirality, were found to guide the self-assembly. Control of the relative position and orientation of the amine groups was achieved, in the case of enantiopure compounds. Interestingly, racemates led to both racemic conglomerate and solid solution formation, with a concomitant loss of positional and orientational control of the amino groups as a result.

  DOI：

  10.1021/ja209018u
• 作为产物：
  描述：

  (S)-2-Fmoc-氨基庚二酸-7-叔丁酯 在 甲酸 作用下， 反应 20.0h， 以100%的产率得到(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)heptanedioic acid
  参考文献：
  名称：

  Controlling the Position of Functional Groups at the Liquid/Solid Interface: Impact of Molecular Symmetry and Chirality

  摘要：

  With the aim of controlling the position of functional groups in a substrate-supported monolayer, a new family of functionalized linear alkyl chains was designed and synthesized, aided by molecular mechanics and dynamics simulations of its two-dimensional self-assembly on graphite. The self-assembly of these amino functionalized diamides at the liquid/solid interface was investigated with scanning tunneling microscopy. Intermolecular hydrogen-bonding interactions involving amides, combined with the effect of molecular symmetry and chirality, were found to guide the self-assembly. Control of the relative position and orientation of the amine groups was achieved, in the case of enantiopure compounds. Interestingly, racemates led to both racemic conglomerate and solid solution formation, with a concomitant loss of positional and orientational control of the amino groups as a result.

  DOI：

  10.1021/ja209018u

文献信息

• Controlling the Position of Functional Groups at the Liquid/Solid Interface: Impact of Molecular Symmetry and Chirality
  作者：Inge De Cat、Cristian Gobbo、Bernard Van Averbeke、Roberto Lazzaroni、Steven De Feyter、Jan van Esch

  DOI：10.1021/ja209018u

  日期：2011.12.28

  With the aim of controlling the position of functional groups in a substrate-supported monolayer, a new family of functionalized linear alkyl chains was designed and synthesized, aided by molecular mechanics and dynamics simulations of its two-dimensional self-assembly on graphite. The self-assembly of these amino functionalized diamides at the liquid/solid interface was investigated with scanning tunneling microscopy. Intermolecular hydrogen-bonding interactions involving amides, combined with the effect of molecular symmetry and chirality, were found to guide the self-assembly. Control of the relative position and orientation of the amine groups was achieved, in the case of enantiopure compounds. Interestingly, racemates led to both racemic conglomerate and solid solution formation, with a concomitant loss of positional and orientational control of the amino groups as a result.