10-isopropyl-9-anthracenone | 141272-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-isopropyl-9-anthracenone
• 英文别名: 10-propan-2-yl-10H-anthracen-9-one
• CAS: 141272-06-2
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: UEEKWILNJIBHAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  9-Isopropyl-9,10-dihydroanthracene 在 sodium dichromate 作用下， 以 溶剂黄146 为溶剂， 反应 72.0h， 以90%的产率得到10-isopropyl-9-anthracenone
  参考文献：
  名称：

  Crystal and molecular structure of 10-substituted 9-anthracenones. Substituent size as the controlling factor for the nonplanarity of the central ring

  摘要：

  MM2 calculations for a series of 10-R-9-anthracenones demonstrate an increase of the folding of the central ring with increasing size of the substituent. All the substituents considered prefer the pseudoaxial position except fluorine, which prefers the pseudoequatorial orientation. The anthracenone moiety approaches planarity when the size of the substituents approaches the size of the hydrogen atom. The planar conformation for 9-anthracenone is also shown by vibrational frequency calculations to be a true potential energy minimum at the ab initio 3-21G level. X-ray structure determination shows that 10-R-9-anthracenones (R = Me, iPr, tBu, Ph, and Br) generally exhibit the structural features predicted by MM2 calculations for the isolated molecules. However, 10-Me and 10-Ph-9-anthracenones are found to be significantly less folded than calculated by MM2, the discrepancy being attributed to the crystal packing forces. Consideration of the theoretical as well as the experimental results leads to the conclusion that the parent 9-anthracenone is expected to be planar in the crystal state.

  DOI：

  10.1021/jo00038a011

文献信息

• US8173274B2
  申请人：——

  公开号：US8173274B2

  公开（公告）日：2012-05-08
• Crystal and molecular structure of 10-substituted 9-anthracenones. Substituent size as the controlling factor for the nonplanarity of the central ring
  作者：Andrzej Sygula、Renata Sygula、Frank R. Fronczek、Peter W. Rabideau

  DOI：10.1021/jo00038a011

  日期：1992.6

  MM2 calculations for a series of 10-R-9-anthracenones demonstrate an increase of the folding of the central ring with increasing size of the substituent. All the substituents considered prefer the pseudoaxial position except fluorine, which prefers the pseudoequatorial orientation. The anthracenone moiety approaches planarity when the size of the substituents approaches the size of the hydrogen atom. The planar conformation for 9-anthracenone is also shown by vibrational frequency calculations to be a true potential energy minimum at the ab initio 3-21G level. X-ray structure determination shows that 10-R-9-anthracenones (R = Me, iPr, tBu, Ph, and Br) generally exhibit the structural features predicted by MM2 calculations for the isolated molecules. However, 10-Me and 10-Ph-9-anthracenones are found to be significantly less folded than calculated by MM2, the discrepancy being attributed to the crystal packing forces. Consideration of the theoretical as well as the experimental results leads to the conclusion that the parent 9-anthracenone is expected to be planar in the crystal state.