9-Isopropyl-9,10-dihydroanthracene | 17573-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-Isopropyl-9,10-dihydroanthracene
• 英文别名: 9,10-Dihydro-9-isopropyl-anthracen；9-Isopropyl-9,10-dihydroanthracen；9-Propan-2-yl-9,10-dihydroanthracene
• CAS: 17573-50-1
• 化学式: C₁₇H₁₈
• 分子量: 222.33
• InChiKey: DHGGRMOYMGFLBU-UHFFFAOYSA-N

物化性质

• 沸点：
  324.7±22.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  9,10-二氢蒽 、 2-溴丙烷 在 正丁基锂 作用下， 生成 9-Isopropyl-9,10-dihydroanthracene
  参考文献：
  名称：

  Deprotonation/alkylation reactions of monoalkyl-9,10-dihydroanthracenes and -7,12-dihydropleiadenes. Stereochemical outcome and anion models

  摘要：

  DOI：

  10.1021/jo00354a024

文献信息

• Substituent effect on the electrochemical oxidation of arylmethyl anions. 3. Effect of methyl substitution on diarylmethyl anions
  作者：Shelton Bank、Alanna Schepartz、Paul Giammatteo、Jon Zubieta

  DOI：10.1021/jo00168a017

  日期：1983.10
• Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg, Chemische Berichte, 1990, vol. 123, # 7, p. 1507 - 1515
  作者：Bogdanovic, Borislav、Janke, Nikolaus、Kinzelmann, Hans-Georg

  DOI：——

  日期：——
• Arene hydrides. 3. Selective 1,4-reduction of chalcone with anthracene hydride via base-induced fragmentation of their Michael adduct
  作者：Helmut Stamm、Andreas Sommer、Andreas Onistschenko、Anton Woderer

  DOI：10.1021/jo00375a042

  日期：1986.12
• Formation of mono- and dianions of polycyclic hydrocarbons through deprotonation with the alkylithium-N,N,N',N'-tetramethylethylenediamine complex. Convenient general method of dehydrogenation
  作者：Ronald G. Harvey、Hee Cho

  DOI：10.1021/ja00815a023

  日期：1974.4
• 9-Isopropylidene-9,10-dihydroanthracene. Synthesis, stereochemistry, and the effect of 10-alkyl group size on the equilibrium with 9-isopropyl-10-alkylanthracene
  作者：Hee Cho、Ronald G. Harvey、Peter W. Rabideau

  DOI：10.1021/ja00838a030

  日期：1975.3