9,9-dimethyl-9H-xanthene-4,5-dicarboxylic acid | 178915-22-5

• 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: 9,9-dimethyl-9H-xanthene-4,5-dicarboxylic acid
• 英文别名: 9H-Xanthene-4,5-dicarboxylic acid, 9,9-dimethyl-；9,9-dimethylxanthene-4,5-dicarboxylic acid
• CAS: 178915-22-5
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: SHERBJQCYZAPRP-UHFFFAOYSA-N

物化性质

• 沸点：
  504.6±50.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9,9-dimethyl-9H-xanthene-4,5-dicarboxylic acid 在 氢氧化钾 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 46.0h， 生成 9,9-dimethyl-9H-xanthene-4,5-diamine
  参考文献：
  名称：

  Photoinduced Hinge-Like Molecular Motion:  Studies on Xanthene-Based Cyclic Azobenzene Dimers

  摘要：

  Molecular devices incorporating azobenzene units represent active components of smart systems, as they are capable of exhibiting photoregulated cooperative molecular motion. Herein, we describe the synthesis, X-ray crystal analysis, and photochemical and thermal studies of a xanthene based cyclic azobenzene dimer and its precursor. The trans-trans isomer of the azobenzene dimer upon photoirradiation transforms to the cis-cis isomer through an intermediate trans-cis isomer. The X-ray crystal structures of the trans-trans isomer (open) and the cis-cis isomer (closed) provide unambiguous proof for the hinge-like molecular motion in this class of molecules. The inferences drawn from photochemical and thermal studies shed light on the effect of varied substitution and cyclic structures on the different transitions. The lifetime of the cis-cis isomer is estimated to be 6.43 years, whereas the trans-cis isomer is short-lived (2.73 min) at 303 K. A rational explanation for the relative stability of the different isomers is derived from the isokinetic plot and theoretical calculations.

  DOI：

  10.1021/jo0513616
• 作为产物：
  描述：

  9,9-dimethyl-9H-xanthene-4,5-dicarbaldehyde 在 jones reagent 作用下， 以 丙酮 为溶剂， 以95%的产率得到9,9-dimethyl-9H-xanthene-4,5-dicarboxylic acid
  参考文献：
  名称：

  Photoinduced Hinge-Like Molecular Motion:  Studies on Xanthene-Based Cyclic Azobenzene Dimers

  摘要：

  Molecular devices incorporating azobenzene units represent active components of smart systems, as they are capable of exhibiting photoregulated cooperative molecular motion. Herein, we describe the synthesis, X-ray crystal analysis, and photochemical and thermal studies of a xanthene based cyclic azobenzene dimer and its precursor. The trans-trans isomer of the azobenzene dimer upon photoirradiation transforms to the cis-cis isomer through an intermediate trans-cis isomer. The X-ray crystal structures of the trans-trans isomer (open) and the cis-cis isomer (closed) provide unambiguous proof for the hinge-like molecular motion in this class of molecules. The inferences drawn from photochemical and thermal studies shed light on the effect of varied substitution and cyclic structures on the different transitions. The lifetime of the cis-cis isomer is estimated to be 6.43 years, whereas the trans-cis isomer is short-lived (2.73 min) at 303 K. A rational explanation for the relative stability of the different isomers is derived from the isokinetic plot and theoretical calculations.

  DOI：

  10.1021/jo0513616

文献信息

• Synthesis and evaluation of 9,9-dimethylxanthene tricyclics against trypanothione reductase, Trypanosoma brucei , Trypanosoma cruzi and Leishmania donovani
  作者：Kelly Chibale、Mark Visser、Vanessa Yardley、Simon L. Croft、Alan H. Fairlamb

  DOI：10.1016/s0960-894x(00)00154-2

  日期：2000.6

  Derivatives of 9,9-dimethylxanthene were synthesised and evaluated against trypanothione reductase (TR) and in vitro against parasitic trypanosomes and leishmania. High in vitro antiparasitic activity was observed for some derivatives with one compound showing high activity against all three parasites (ED50 values of 0.02, 0.48 and 0.32 mu M, for Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, respectively). The lack of correlation between inhibitory activity against TR and ED50 values suggests that TR is not the target. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of xanthene-derived diimine and iminophosphine compounds as potential chiral bidentate ligands
  作者：Grégory Malaisé、Laurent Barloy、John A Osborn

  DOI：10.1016/s0040-4039(01)01588-x

  日期：2001.10

  The synthesis of one diimine and two iminophosphine chiral ligands bearing a xanthene backbone in, respectively, four and five steps is described. The diimine is characterised by X-ray crystallography. A preliminary test in palladium-catalysed asymmetric allylic alkylation is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Photoinduced Hinge-Like Molecular Motion:  Studies on Xanthene-Based Cyclic Azobenzene Dimers
  作者：S. Anitha Nagamani、Yasuo Norikane、Nobuyuki Tamaoki

  DOI：10.1021/jo0513616

  日期：2005.11.1

  Molecular devices incorporating azobenzene units represent active components of smart systems, as they are capable of exhibiting photoregulated cooperative molecular motion. Herein, we describe the synthesis, X-ray crystal analysis, and photochemical and thermal studies of a xanthene based cyclic azobenzene dimer and its precursor. The trans-trans isomer of the azobenzene dimer upon photoirradiation transforms to the cis-cis isomer through an intermediate trans-cis isomer. The X-ray crystal structures of the trans-trans isomer (open) and the cis-cis isomer (closed) provide unambiguous proof for the hinge-like molecular motion in this class of molecules. The inferences drawn from photochemical and thermal studies shed light on the effect of varied substitution and cyclic structures on the different transitions. The lifetime of the cis-cis isomer is estimated to be 6.43 years, whereas the trans-cis isomer is short-lived (2.73 min) at 303 K. A rational explanation for the relative stability of the different isomers is derived from the isokinetic plot and theoretical calculations.