6^A-deoxy-6^A-methylamino-β-cyclodextrin | 84346-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A-deoxy-6^A-methylamino-β-cyclodextrin
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30-hexakis(hydroxymethyl)-35-(methylaminomethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• CAS: 84346-56-5
• 化学式: C₄₃H₇₃NO₃₄
• 分子量: 1148.04
• InChiKey: JNZFWIYFEZUWSW-QASYHWDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.8
• 重原子数：
  78
• 可旋转键数：
  8
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  546
• 氢给体数：
  21
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  6^A-deoxy-6^A-methylamino-β-cyclodextrin 、 3-苯基-2-丙烯酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以12%的产率得到trans-6^A-deoxy-6^A-(N-methylcinnamido)-β-cyclodextrin
  参考文献：
  名称：

  Harnessing the Energy of Molecular Recognition in a Nanomachine Having a Photochemical On/Off Switch

  摘要：

  6A-Deoxy-6A-(N-methyl-3-phenylpropionamido)-beta-cyclodextrin operates as a molecular machine, where the amide group serves as a torsion bar to harness the work output resulting from extraction of 1-adamantanol and consequent complexation of the aryl substituent by the cyclodextrin, when the latter behave as the piston and cylinder, respectively, of a molecular pump. At 25 degrees C, the complexation changes the ratio of the amide (Z)- and (E)-isomers from 2.4:1 to 25:1, on which basis the work performed on the amide bond is calculated to be 1.4 kcal mol-1. trans-6A-Deoxy-6A-(N-methylcinnamido)-beta-cyclodextrin and the cis isomer function as a more advanced version of the machine, with the alkene moiety serving as a photochemical on/off switch. Irradiation at 300 nm converts the trans cinnamide to the cis isomer, while the reverse process occurs at 254 nm. With the cis isomer there is little interaction of the phenyl group with the cyclodextrin cavity, so in that mode the machine is turned off. By contrast, complexation of the aryl substituent by the cyclodextrin occurs with the trans cinnamide and changes the ratio of the amide (Z)- and (E)-isomers from 2.6:1 to 100:1. Consequently, in this mode the machine is turned on, and the work harnessed by the amide bond is 2.1 kcal mol-1.

  DOI：

  10.1021/ja0651761
• 作为产物：
  描述：

  甲胺 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 potassium iodide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 42.0h， 以23%的产率得到6^A-deoxy-6^A-methylamino-β-cyclodextrin
  参考文献：
  名称：

  Harnessing the Energy of Molecular Recognition in a Nanomachine Having a Photochemical On/Off Switch

  摘要：

  6A-Deoxy-6A-(N-methyl-3-phenylpropionamido)-beta-cyclodextrin operates as a molecular machine, where the amide group serves as a torsion bar to harness the work output resulting from extraction of 1-adamantanol and consequent complexation of the aryl substituent by the cyclodextrin, when the latter behave as the piston and cylinder, respectively, of a molecular pump. At 25 degrees C, the complexation changes the ratio of the amide (Z)- and (E)-isomers from 2.4:1 to 25:1, on which basis the work performed on the amide bond is calculated to be 1.4 kcal mol-1. trans-6A-Deoxy-6A-(N-methylcinnamido)-beta-cyclodextrin and the cis isomer function as a more advanced version of the machine, with the alkene moiety serving as a photochemical on/off switch. Irradiation at 300 nm converts the trans cinnamide to the cis isomer, while the reverse process occurs at 254 nm. With the cis isomer there is little interaction of the phenyl group with the cyclodextrin cavity, so in that mode the machine is turned off. By contrast, complexation of the aryl substituent by the cyclodextrin occurs with the trans cinnamide and changes the ratio of the amide (Z)- and (E)-isomers from 2.6:1 to 100:1. Consequently, in this mode the machine is turned on, and the work harnessed by the amide bond is 2.1 kcal mol-1.

  DOI：

  10.1021/ja0651761