9-(2-methylphenyl)-3,4,5,6,9,10-hexahydroxanthene-1,8(2H,7H)-dione | 259220-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 9-(2-methylphenyl)-3,4,5,6,9,10-hexahydroxanthene-1,8(2H,7H)-dione
• 英文别名: 9-(2-methylphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(2-methylphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 259220-74-1
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: FUXLZWUFQKWYMB-UHFFFAOYSA-N

物化性质

• 熔点：
  220-222 °C
• 沸点：
  515.1±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(2-methylphenyl)-3,4,5,6,9,10-hexahydroxanthene-1,8(2H,7H)-dione 在 氯磺酸 作用下， 以 乙醇 为溶剂， 生成 3-(1,8-Dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)-4,N,N-trimethyl-benzenesulfonamide
  参考文献：
  名称：

  CHLOROSULFONATION OF 9-ARYLOCTAHYDROXANTHEN-1,8-DIONES

  摘要：

  The 9-aryloctathydroxanthen-1,8-diones (3, 4-24) were prepared by reaction of cyclohexan-1,3-dione (1) with selected arylaldehydes. The xanthendiones (4-9, 11, 12, 18, 21, 22) were successfully reacted with chlorosulfonic acid, and the crude sulfonyl chlorides were converted into 15 sulfonamides (26-40) for screening as potential pesticides. Attempted chlorosulfonation of the xanthendiones (13-17) was unsuccessful. alpha-Methylcinnamaldehyde was reacted with cyclohexandione (1) to yield the corresponding xanthendione derivative (23). On the other hand, with o-methoxycinnamaldehyde an impure product formed and the p-methoxy isomer afforded the corresponding 2-arylpyran (25). The NMR spectral data of the compounds are briefly discussed.

  DOI：

  10.1080/10426500490494741
• 作为产物：
  描述：

  2-甲基苯甲醛 在 哌啶 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 生成 9-(2-methylphenyl)-3,4,5,6,9,10-hexahydroxanthene-1,8(2H,7H)-dione
  参考文献：
  名称：

  CHLOROSULFONATION OF 9-ARYLOCTAHYDROXANTHEN-1,8-DIONES

  摘要：

  The 9-aryloctathydroxanthen-1,8-diones (3, 4-24) were prepared by reaction of cyclohexan-1,3-dione (1) with selected arylaldehydes. The xanthendiones (4-9, 11, 12, 18, 21, 22) were successfully reacted with chlorosulfonic acid, and the crude sulfonyl chlorides were converted into 15 sulfonamides (26-40) for screening as potential pesticides. Attempted chlorosulfonation of the xanthendiones (13-17) was unsuccessful. alpha-Methylcinnamaldehyde was reacted with cyclohexandione (1) to yield the corresponding xanthendione derivative (23). On the other hand, with o-methoxycinnamaldehyde an impure product formed and the p-methoxy isomer afforded the corresponding 2-arylpyran (25). The NMR spectral data of the compounds are briefly discussed.

  DOI：

  10.1080/10426500490494741

文献信息

• A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions
  作者：Behrooz Maleki、Shahram Barzegar、Zeinalabedin Sepehr、Mina Kermanian、Reza Tayebee

  DOI：10.1007/s13738-012-0092-5

  日期：2012.10

  simple, efficient, and environmentally benign route was developed for the preparation of 14-aryl or alkyl-14H-dibenzo[a,j]xanthene, 1,8-dioxo-octahydroxanthene and 12-aryl—8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones from condensation of various aldehydes with (i) β-naphthol, (ii) cyclic 1,3-dicarbonyl compounds and (iii) β-naphthol and cyclic 1,3-dicarbonyl compounds, using novel polymeric catalyst [poly(AMPS-co-AA)]

  开发了一种简单，有效且环境友好的方法，用于制备14-芳基或烷基14 H-二苯并[a，j]氧杂蒽，1,8-二氧代-八氢氧杂蒽和12-芳基-8,9,10，各种醛与（i）β-萘酚，（ii）环状1,3-二羰基化合物和（iii）β-萘酚和环状1,3-二羰基化合物缩合而成的12-四氢苯并[a]黄嘌呤-11-酮，在无溶剂条件下使用新型聚合物催化剂[聚（AMPS-co-AA）]。使用容易获得的催化剂，更短的反应时间，更好的产率，反应的简单性，非均相系统和容易的后处理是本方法的优点。
• N-sulfonic acid poly(4-vinylpyridinium) chloride: A novel polymeric and reusable catalyst for the preparation of xanthenes derivatives
  作者：Frahad Shirini、Masoumeh Abedini、Reyhaneh Pourhasan

  DOI：10.1016/j.dyepig.2013.04.036

  日期：2013.10

  A simple and efficient procedure for the preparation of 14-aryl-14H-dibenzo[a,j]xanthenes, 1,8-dioxooctahydroxanthenes and tetrahydrobenzo[a]xanthene-11-ones is described using N-sulfonic acid poly(4-vinylpyridinium) chloride (NSPVPC) as a heterogeneous and efficient catalyst under solvent-free conditions. The structures of the products were characterized by their physical constants, comparison with authentic samples and IR, H-1 NMR and C-13 NMR spectroscopy. Simple methodologies, easy work-up procedure, easy preparation of the catalyst, excellent yields and short reaction times are some advantages of this work. Further, the catalyst can be reused and recovered for several times without significant decrease in its activity. (C) 2013 Elsevier Ltd. All rights reserved.
• ——
  作者：Marco Brito-Arias、Manuel Tapia-Albarrán、Itzia Padilla-Martínez、Francisco Martínez-Martínez、Georgina Espinosa、Elies Molins、Enrique Espinosa

  DOI：10.1023/a:1009583417391

  日期：——

  Several 9-(2-R phenyl)xanthenediones have been synthesized and the x-ray diffraction structure for the 2-methylphenyl derivative (4b) has been determined. This compound crystallizes in the monoclinic system, space group P2(1)/n, with a = 11.729 (3), b = 9.674 (3), c = 14.628 (4) Angstrom, and beta = 106.30 degrees. It presents a partially hydrogenated xanthene system in distorted boat conformation for the heterocyclic central ring, and an almost ideal envelope conformation for the outer rings. The aromatic substituent at the ninth position is at 84 degrees in angle with the xanthene system.