5-[2-(acetylamino)anthracen-9-yl]-2-methylbenzaldehyde | 289059-03-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 5-[2-(acetylamino)anthracen-9-yl]-2-methylbenzaldehyde
• CAS: 289059-03-6
• 化学式: C₂₄H₁₉NO₂
• 分子量: 353.42
• InChiKey: DLUMROJGOPXBEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-[2-(acetylamino)anthracen-9-yl]-2-methylbenzaldehyde 在 lithium hexamethyldisilazane 、 亚硝酸异戊酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.17h， 生成 (Z)-2-(acetylamino)-9,10-dihydro-9-[4-methyl-3-[2-(7-methoxy-2-naphthalenyl)ethenyl]phenyl]-9,10[1',2']-benzenoanthracene
  参考文献：
  名称：

  A Rationally Designed Prototype of a Molecular Motor

  摘要：

  A proof of principle of the first rationally designed, chemically powered, molecular-scale motor is described. The thermodynamic considerations leading to the choice of 6a and 7a as the initial prototypes are provided, and the synthesis of 6a and 7a and the separation of them from their atropisomers are detailed. The phosgene-powered unidirectional rotation of 6a to its rotamer 6b is demonstrated. It is further established that shortening the length of the tether (-->7a) changes the rate-limiting step and accelerates the speed of rotation.

  DOI：

  10.1021/ja001048f
• 作为产物：
  描述：

  2-(acetylamino)anthracene 在 四(三苯基膦)钯 、 正丁基锂 、 甲基锂 、 溴 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 5-[2-(acetylamino)anthracen-9-yl]-2-methylbenzaldehyde
  参考文献：
  名称：

  A Rationally Designed Prototype of a Molecular Motor

  摘要：

  A proof of principle of the first rationally designed, chemically powered, molecular-scale motor is described. The thermodynamic considerations leading to the choice of 6a and 7a as the initial prototypes are provided, and the synthesis of 6a and 7a and the separation of them from their atropisomers are detailed. The phosgene-powered unidirectional rotation of 6a to its rotamer 6b is demonstrated. It is further established that shortening the length of the tether (-->7a) changes the rate-limiting step and accelerates the speed of rotation.

  DOI：

  10.1021/ja001048f