(9H-fluoren-9-yl)methyl {(3-hydroxypropylcarbamoyl)methyl}carbamate | 153996-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl {(3-hydroxypropylcarbamoyl)methyl}carbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-[2-(3-hydroxypropylamino)-2-oxoethyl]carbamate
• CAS: 153996-31-7
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: ZXAPUKFOZYNGCC-UHFFFAOYSA-N

物化性质

• 沸点：
  653.0±45.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl {(3-hydroxypropylcarbamoyl)methyl}carbamate 在 potassium fluoride 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 22.0h， 以17.2%的产率得到9-亚甲基芴
  参考文献：
  名称：

  A new method for cleavage of silicon–carbon linkers on glass plate supports with applications to solid-phase syntheses on silica resins

  摘要：

  We describe herein a novel and facile method for the cleavage of a silicon-based linker on solid-phase supports such as glass plates or silica resin. The linker was efficiently cleaved by oxidation of the silicon-carbon bond (Tamao-Kumada oxidation) to release the functionalized molecule. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.042
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (9H-fluoren-9-yl)methyl {(3-hydroxypropylcarbamoyl)methyl}carbamate
  参考文献：
  名称：

  Large Molecular Assembly of Amphotericin B Formed in Ergosterol-Containing Membrane Evidenced by Solid-State NMR of Intramolecular Bridged Derivative

  摘要：

  Amphotericin B (AmB 1) is known to assemble and form an ion channel across biomembranes. We have recently reported that conformation-restricted derivatives of AmB 2-4 show different ergosterol preferences in ion-channel assays, which suggested that the orientation of the mycosamine strongly affects the sterol selectivity of AmB. The data allowed us to assume that compound 3 showing the highest selectivity would reflect the active conformation of AmB in the channel assembly. In this study, to gain further insight into the active conformation of AmB, we prepared a new intramolecular-bridged derivative 5, where the linker encompassed a hydrophilic glycine moiety. The derivative has almost equivalent ion-channel activity to those of AmB and 3. The antifungal activity of 5 compared with 3 improves significantly, possibly because the increasing hydrophilicity in the linker enhances the penetrability through the fungal cell wall. Conformation of 5 was well converged and very similar to that of 3, thus further supporting the notion that the conformations of these derivatives reproduce the active structure of AmB in the channel complex. Then we used the derivative to probe the mobility of AmB in the membrane by solid-state NMR. To measure dipolar couplings and chemical shift anisotropies, we incorporated [1-C-13, N-15] glycine into the linker. The results indicate that 5 is mostly immobilized in ergosterol-containing DMPC bilayers, implying formation of large aggregates of 5. Meanwhile some fraction of 5 remains mobile in sterol-free DMPC bilayers, suggesting promotion of AmB aggregation by ergosterol.

  DOI：

  10.1021/ja063433w

文献信息

• Symmetrical structure allowing the selective multiple release of a defined quantity of peptide from a single bead of polymeric support
  作者：Petr Kočiš、Viktor Krchňák、Michal Lebl

  DOI：10.1016/s0040-4039(00)79300-2

  日期：1993.11

  A linker based on the combination of two molecules of iminodiacetic acid that allows for the release of peptide molecule from the polymeric bead in two equimolar portions in two distinct steps was designed and synthesized and its predicted properties were verified.
• Large Molecular Assembly of Amphotericin B Formed in Ergosterol-Containing Membrane Evidenced by Solid-State NMR of Intramolecular Bridged Derivative
  作者：Nobuaki Matsumori、Yuri Sawada、Michio Murata

  DOI：10.1021/ja063433w

  日期：2006.9.1

  Amphotericin B (AmB 1) is known to assemble and form an ion channel across biomembranes. We have recently reported that conformation-restricted derivatives of AmB 2-4 show different ergosterol preferences in ion-channel assays, which suggested that the orientation of the mycosamine strongly affects the sterol selectivity of AmB. The data allowed us to assume that compound 3 showing the highest selectivity would reflect the active conformation of AmB in the channel assembly. In this study, to gain further insight into the active conformation of AmB, we prepared a new intramolecular-bridged derivative 5, where the linker encompassed a hydrophilic glycine moiety. The derivative has almost equivalent ion-channel activity to those of AmB and 3. The antifungal activity of 5 compared with 3 improves significantly, possibly because the increasing hydrophilicity in the linker enhances the penetrability through the fungal cell wall. Conformation of 5 was well converged and very similar to that of 3, thus further supporting the notion that the conformations of these derivatives reproduce the active structure of AmB in the channel complex. Then we used the derivative to probe the mobility of AmB in the membrane by solid-state NMR. To measure dipolar couplings and chemical shift anisotropies, we incorporated [1-C-13, N-15] glycine into the linker. The results indicate that 5 is mostly immobilized in ergosterol-containing DMPC bilayers, implying formation of large aggregates of 5. Meanwhile some fraction of 5 remains mobile in sterol-free DMPC bilayers, suggesting promotion of AmB aggregation by ergosterol.
• A new method for cleavage of silicon–carbon linkers on glass plate supports with applications to solid-phase syntheses on silica resins
  作者：Takeshi Terauchi、Sachiko Machida、Shiro Komba

  DOI：10.1016/j.tetlet.2010.01.042

  日期：2010.3

  We describe herein a novel and facile method for the cleavage of a silicon-based linker on solid-phase supports such as glass plates or silica resin. The linker was efficiently cleaved by oxidation of the silicon-carbon bond (Tamao-Kumada oxidation) to release the functionalized molecule. (C) 2010 Elsevier Ltd. All rights reserved.