1-Chloro-8-[(S)-2-(tetrahydro-pyran-2-yloxy)-propoxy]-anthraquinone | 189103-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Chloro-8-[(S)-2-(tetrahydro-pyran-2-yloxy)-propoxy]-anthraquinone
• 英文别名: 1-chloro-8-[(2S)-2-(oxan-2-yloxy)propoxy]anthracene-9,10-dione
• CAS: 189103-88-6
• 化学式: C₂₂H₂₁ClO₅
• 分子量: 400.859
• InChiKey: BLSJEXDQQBXSFA-FVRDMJKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Chloro-8-[(S)-2-(tetrahydro-pyran-2-yloxy)-propoxy]-anthraquinone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 1-[(S)-2-(Tetrahydro-pyran-2-yloxy)-propoxy]-anthraquinone
  参考文献：
  名称：

  Unusual monosubstitution-monodechlorination product in the reaction of 1,8-dichloroanthraquinone with ( S )-(−)-2-(tetrahydropyranyloxy)-1-propanol

  摘要：

  Treatment of 1,8-dichloroanthraquinone with (S)-(-)-2-(tetrahydropyranyloxy)-1-propanol in the presence of NaH in THF gave monosubstitued-monodechlorinated product 2 and desired 1,8-disubstitued product 1. Molecular mechanics calculations and H-1 NMR experiments suggest that the tetrahydropyranyl group in the side chain of monosubstituted-monochloro product 3 hinders the second reaction site and the Na+ cation interacts with the oxygen atoms of the side chain and ketone function allowing, the hydride anion access to the second reaction site. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00146-4
• 作为产物：
  描述：

  1,8-二氯蒽醌 、 (2S)-2-[(四氢-2H-吡喃-2-基)氧基]-1-丙醇 在 sodium hydride 作用下， 生成 1-Chloro-8-[(S)-2-(tetrahydro-pyran-2-yloxy)-propoxy]-anthraquinone 、 1,8-Bis-[(S)-2-(tetrahydro-pyran-2-yloxy)-propoxy]-anthraquinone
  参考文献：
  名称：

  Unusual monosubstitution-monodechlorination product in the reaction of 1,8-dichloroanthraquinone with ( S )-(−)-2-(tetrahydropyranyloxy)-1-propanol

  摘要：

  Treatment of 1,8-dichloroanthraquinone with (S)-(-)-2-(tetrahydropyranyloxy)-1-propanol in the presence of NaH in THF gave monosubstitued-monodechlorinated product 2 and desired 1,8-disubstitued product 1. Molecular mechanics calculations and H-1 NMR experiments suggest that the tetrahydropyranyl group in the side chain of monosubstituted-monochloro product 3 hinders the second reaction site and the Na+ cation interacts with the oxygen atoms of the side chain and ketone function allowing, the hydride anion access to the second reaction site. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00146-4

文献信息

• Unusual monosubstitution-monodechlorination product in the reaction of 1,8-dichloroanthraquinone with ( S )-(−)-2-(tetrahydropyranyloxy)-1-propanol
  作者：Yoichi Habata、Jerald S. Bradshaw、Ryan W. Nelson、Reed M. Izatt

  DOI：10.1016/s0040-4020(97)00146-4

  日期：1997.3

  Treatment of 1,8-dichloroanthraquinone with (S)-(-)-2-(tetrahydropyranyloxy)-1-propanol in the presence of NaH in THF gave monosubstitued-monodechlorinated product 2 and desired 1,8-disubstitued product 1. Molecular mechanics calculations and H-1 NMR experiments suggest that the tetrahydropyranyl group in the side chain of monosubstituted-monochloro product 3 hinders the second reaction site and the Na+ cation interacts with the oxygen atoms of the side chain and ketone function allowing, the hydride anion access to the second reaction site. (C) 1997 Elsevier Science Ltd.