tert-butyl 2-methoxy-9-oxoacridine-10(9H)-carboxylate | 1206462-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl 2-methoxy-9-oxoacridine-10(9H)-carboxylate
• 英文别名: Tert-butyl 2-methoxy-9-oxoacridine-10-carboxylate
• CAS: 1206462-02-3
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: WDAGHAZMCSCNRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-methoxy-9-oxoacridine-10(9H)-carboxylate 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以80%的产率得到tert-butyl 2-methoxy-9-thioxoacridine-10(9H)-carboxylate
  参考文献：
  名称：

  Ultrafast Light-Driven Nanomotors Based on an Acridane Stator

  摘要：

  A series Of Molecular motors featuring a symmetrical acridane stator is reported. Photochemical and thermal isomerization experiments confirm that this stator, in combination with a thiopyran rotor, results in molecular rotary motion in which the rate-determining thermal helix inversion proceeds effectively only at temperatures above 373 K. The introduction of a cyclopentanylidene rotor unit results in a decrease in steric hindrance with respect to the stator, and as a consequence, a 10(12)-fold increase in the rate of thermal helix inversion is observed. Nanosecond transient absorption spectroscopy allows for the thermal processes to be followed accurately at ambient temperature. The rotary motor is shown to be able to operate at 0.5 MHz rotational frequencies Under optimal conditions.

  DOI：

  10.1021/jo902207x
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-methoxy-9(10H)-acridinone 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 11.0h， 以68%的产率得到tert-butyl 2-methoxy-9-oxoacridine-10(9H)-carboxylate
  参考文献：
  名称：

  Ultrafast Light-Driven Nanomotors Based on an Acridane Stator

  摘要：

  A series Of Molecular motors featuring a symmetrical acridane stator is reported. Photochemical and thermal isomerization experiments confirm that this stator, in combination with a thiopyran rotor, results in molecular rotary motion in which the rate-determining thermal helix inversion proceeds effectively only at temperatures above 373 K. The introduction of a cyclopentanylidene rotor unit results in a decrease in steric hindrance with respect to the stator, and as a consequence, a 10(12)-fold increase in the rate of thermal helix inversion is observed. Nanosecond transient absorption spectroscopy allows for the thermal processes to be followed accurately at ambient temperature. The rotary motor is shown to be able to operate at 0.5 MHz rotational frequencies Under optimal conditions.

  DOI：

  10.1021/jo902207x

文献信息

• Ultrafast Light-Driven Nanomotors Based on an Acridane Stator
  作者：Artem A. Kulago、Emile M. Mes、Martin Klok、Auke Meetsma、Albert M. Brouwer、Ben L. Feringa

  DOI：10.1021/jo902207x

  日期：2010.2.5

  A series Of Molecular motors featuring a symmetrical acridane stator is reported. Photochemical and thermal isomerization experiments confirm that this stator, in combination with a thiopyran rotor, results in molecular rotary motion in which the rate-determining thermal helix inversion proceeds effectively only at temperatures above 373 K. The introduction of a cyclopentanylidene rotor unit results in a decrease in steric hindrance with respect to the stator, and as a consequence, a 10(12)-fold increase in the rate of thermal helix inversion is observed. Nanosecond transient absorption spectroscopy allows for the thermal processes to be followed accurately at ambient temperature. The rotary motor is shown to be able to operate at 0.5 MHz rotational frequencies Under optimal conditions.