9-(3-methoxyphenyl)-9H-xanthen-9-ol | 42960-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(3-methoxyphenyl)-9H-xanthen-9-ol
• 英文别名: 9-(3-methoxyphenyl)xanthen-9-ol；9-(3-methoxy-phenyl)-xanthen-9-ol；9-Hydroxy-9-(m-methoxyphenyl)xanthen
• CAS: 42960-05-4
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: FMOHCZRKEBOPIU-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  471.4±45.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(3-methoxyphenyl)-9H-xanthen-9-ol 在 甲酸 、 sodium carbonate 作用下， 反应 2.0h， 生成 9-(3-methoxyphenyl)xanthene
  参考文献：
  名称：

  Hinds, John L.; Rajadhyaksha, Shirish N.; Wander, Joseph D., Heterocycles, 1983, vol. 20, # 3, p. 481 - 487

  摘要：

  DOI：
• 作为产物：
  描述：

  占吨酮 、 (3-methoxyphenyl)magnesium bromide 以 乙醚 为溶剂， 反应 6.0h， 生成 9-(3-methoxyphenyl)-9H-xanthen-9-ol
  参考文献：
  名称：

  Electrophilic reactions of xanthylium carbocations produced by flash photolysis of 9-xanthenols

  摘要：

  DOI：

  10.1021/ja00190a030

文献信息

• Inclusion Compounds of Xanthenol Hosts with Morpholine: Structure and Grinding Experiments
  作者：Amina Sayed、Ayesha Jacobs、Jana H. Taljaard

  DOI：10.1007/s10870-013-0424-z

  日期：2013.6

  The host compounds 9-(4-methoxyphenyl)-9H-xanthen-9-ol (H1) and 9-(3-methoxyphenyl)-9H-xanthen-9-ol (H2) form inclusion compounds with morpholine (MORPH). The H1·½MORPH structure crystallised in the monoclinic space group P21/c with Z = 4. The unit cell dimensions were determined as: a = 8.9358(6) Å, b = 15.0970(10) Å, c = 13.1591(9) Å, β = 101.253(2)° and V = 1741.1(2) Å3. The final R indices obtained for this structure was [I > 2σ (I)] R1 = 0.0389 (wR2 = 0.1040). 2H2·2MORPH was solved successfully in P-1 with Z = 2, unit cell dimensions: a = 8.9784(18) Å, b = 12.595(3) Å, c = 18.932(4) Å, α = 77.78(3)º, β = 88.78(3)°, γ = 72.22(3)° and V = 1990.3(9) Å3. For this structure R1 = 0.0438, wR2 = 0.1072 for [I > 2σ (I)]. The compounds obtained from grinding experiments were analysed using powder X-ray diffraction. Inclusion compound of 9-(3-methoxyphenyl)-9H-xanthen-9-ol with morpholine

  .1040。
• Synthesis and cancer cell cytotoxicity of substituted xanthenes
  作者：Rajan Giri、John R. Goodell、Chenguo Xing、Adam Benoit、Harneet Kaur、Hiroshi Hiasa、David M. Ferguson

  DOI：10.1016/j.bmc.2010.01.018

  日期：2010.2

  A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N, N-diethyl]-9-hydroxy-9( 3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 mu M across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e. g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring. (C) 2010 Elsevier Ltd. All rights reserved.
• Quenching behavior of singlet excited 9-arylxanthylium cations
  作者：Maria R. Valentino、Mary K. Boyd

  DOI：10.1021/jo00073a050

  日期：1993.10

  Several 9-arylxanthylium tetrafluoroborate salts (Ar = H, p,m-F, p,m-Me, m-OMe) were synthesized by reaction of the corresponding 9-arylxanthen-9-ol with fluoroboric acid. Spectral characteristics of the xanthyl cations were identical to those previously reported for the cations generated by alternate methods. The 9-arylxanthyl cation fluorescence was quenched by the addition of H2O, MeOH, i-PrOH, and t-BuOH. Stern-Volmer analysis of the fluorescence quenching gave bimolecular excited-state rate constants ranging from 10(6) to 10(10) M-1 s-1, with the larger rate constants associated with electron-donating substituents. Hammett plots of log[k(q)(X)/k(q)(H)] versus sigma(hnu) gave negative p values for each quencher, opposite to the substituent dependence observed for ground-state cations reacting with nucleophiles. The relative quenching order also differs from the order observed for ground-state cation reactions. The mechanism for quenching of the singlet excited 9-arylxanthylium cations is evaluated in terms of nucleophilic attack. The possibility of an electron-transfer mechanism is considered and eliminated.
• NAGAO;YUKINORI;ABE, YUKIHIRO;OYAMA, TSUKASA;ABE, YOSHIMOTO;MISONO, TAKAHI+, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1987) N 10, 1839-1845
  作者：NAGAO、YUKINORI、ABE, YUKIHIRO、OYAMA, TSUKASA、ABE, YOSHIMOTO、MISONO, TAKAHI+

  DOI：——

  日期：——