1,1'-bis(8-chloroanthraquinone) | 42530-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,1'-bis(8-chloroanthraquinone)
• CAS: 42530-52-9
• 化学式: C₂₈H₁₂Cl₂O₄
• 分子量: 483.307
• InChiKey: XLJZAPZBRVLDER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  34.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4-苯二硫醇 、 1,1'-bis(8-chloroanthraquinone) 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 17.0h， 以3%的产率得到
  参考文献：
  名称：

  A chiral, bis-anthraquinone-bridged cyclophane with a large specific rotation

  摘要：

  A wide variety of common TD-DFT methods predict that chiral cyclophane 1 should exhibit a specific rotation ranging from large ([alpha](D) similar to 1000) to unreasonably large ([alpha](D) > 1,000,000) with numerous estimates between these values. Compound 1 was prepared in two steps from 1,8-dichloroanthraquinone, and its X-ray structure showed it to be, as expected, a C-2-symmetric, roughly triangular macrocycle. Compound 1 was resolved into nearly pure enantiomers by chromatography on a chiral support, and the specific rotations of the two components were determined to be [alpha](D)(23)= +1520 and [alpha](D)(23) = -1470. These values are large, but not exceptionally so, and the wildly inaccurate TD-DFT estimates of the specific rotation of compound 1 are shown to be closely related to the failure of the same TD-DFT methods to predict accurately the absorption spectrum of 1. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.016
• 作为产物：
  描述：

  1,8-二氯蒽醌 在 铜 作用下， 反应 0.42h， 以16%的产率得到1,1'-bis(8-chloroanthraquinone)
  参考文献：
  名称：

  A chiral, bis-anthraquinone-bridged cyclophane with a large specific rotation

  摘要：

  A wide variety of common TD-DFT methods predict that chiral cyclophane 1 should exhibit a specific rotation ranging from large ([alpha](D) similar to 1000) to unreasonably large ([alpha](D) > 1,000,000) with numerous estimates between these values. Compound 1 was prepared in two steps from 1,8-dichloroanthraquinone, and its X-ray structure showed it to be, as expected, a C-2-symmetric, roughly triangular macrocycle. Compound 1 was resolved into nearly pure enantiomers by chromatography on a chiral support, and the specific rotations of the two components were determined to be [alpha](D)(23)= +1520 and [alpha](D)(23) = -1470. These values are large, but not exceptionally so, and the wildly inaccurate TD-DFT estimates of the specific rotation of compound 1 are shown to be closely related to the failure of the same TD-DFT methods to predict accurately the absorption spectrum of 1. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.016