3,3,6,6-tetramethyl-9-(3,4-dioxymethylenephenyl)-1,8-dioxo-octahydroxanthene | 30038-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3,3,6,6-tetramethyl-9-(3,4-dioxymethylenephenyl)-1,8-dioxo-octahydroxanthene
• 英文别名: 9-(piperonyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydroxanthene-1,8-dione；3,3,6,6-tetramethyl-9-(1,3-benzodioxol-5-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione；9-(benzo[d][1,3]dioxol-5-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(benzo[d][1,3]dioxol-5-yl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-2H-xanthene-1,8(5H,9H)-dione；9-benzo[1,3]dioxol-5-yl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione；9-Benzo[1,3]dioxol-5-yl-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthen-1,8-dion；9-(1,3-benzodioxol-5-yl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 30038-66-5
• 化学式: C₂₄H₂₆O₅
• mdl: MFCD00478048
• 分子量: 394.467
• InChiKey: SOXANMKWPPVZQF-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C(Solv: ethanol (64-17-5))
• 沸点：
  543.4±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzo[1,3]dioxol-5-yl-bis-(4,4-dimethyl-2,6-dioxo-cyclohexyl)-methane 在 盐酸 作用下， 生成 3,3,6,6-tetramethyl-9-(3,4-dioxymethylenephenyl)-1,8-dioxo-octahydroxanthene
  参考文献：
  名称：

  醛的甲酮衍生物。

  摘要：

  DOI：

  10.1021/jo01171a014

文献信息

• 2,4,6-Trichloro-1,3,5-Triazine-Promoted Synthesis of 1,8-Dioxo-Octahydroxanthenes under Solvent-Free Conditions
  作者：Zhan-Hui Zhang、Xu-Ye Tao

  DOI：10.1071/ch07274

  日期：——

  A practical protocol has been developed for the synthesis of 1,8-dioxo-octahydroxanthenes from aromatic aldehydes and 5,5-dimethylcyclohexane-1,3-dione under solvent-free conditions in the presence of wet 2,4,6-trichloro-1,3,5-triazine (TCT, cyanuric chloride). The desired products were obtained in high yields with a simple and environmentally benign procedure.

  在无溶剂条件下，在湿 2,4,6- 三氯-1,3,5-三嗪（TCT，氯化氰）的存在下，开发了一种以芳香醛和 5,5-二甲基环己烷-1,3-二酮为原料合成 1,8-二氧代八氢蒽的实用方案。该方法简单、环保，能以高产率获得所需的产品。
• CONDENSATION OF AROMATIC ALDEHYDES WITH 5,5-DIMETHYL- 1,3-CYCLOHEXANEDIONE WITHOUT CATALYST
  作者：Shujiang Tu、Jianfeng Zhou、Zaisheng Lu、Xu Deng、Daqing Shi、Suhui Wang

  DOI：10.1081/scc-120012999

  日期：2002.1

  ABSTRACT The condensation of aromatic aldehyde with 5,5-dimethyl-1,3-cyclohexanedione is carried out in ethylene glycol as solvent without catalyst.

  摘要 芳香醛与 5,5-二甲基-1,3-环己二酮的缩合反应是以乙二醇为溶剂，无催化剂进行的。
• Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media
  作者：Kazem D. Safa、Elham Taheri、Maryam Allahvirdinesbat、Aligholi Niaei

  DOI：10.1007/s11164-015-2192-1

  日期：2016.4

  An efficient green method for the syntheses of biologically active xanthene derivatives by use of zeolite-supported transition metal catalysts is described. A Fe-Cu/ZSM-5 heterogeneous catalyst has the highest activity in the one-pot syntheses with a wide range of aldehydes and cyclic 1,3-diketones, under ultrasonic irradiation in water at ambient temperatures. The three-component condensation in the presence of supported metal catalysts is operationally simple, requires no expensive or toxic reagents, and gives high yields in short reaction times.

  描述了一种高效的绿色方法，通过使用分子筛支持的过渡金属催化剂合成生物活性黄烷衍生物。Fe-Cu/ZSM-5杂多催化剂在常温水相超声照射条件下，与多种醛和环状1,3-二酮进行一步合成时表现出最高活性。在支持金属催化剂存在下的三组分缩合反应操作简单，无需昂贵或有毒的试剂，且在短反应时间内能获得高产率。
• Zn[(L)Proline]₂: an eligible candidate for the synthesis of xanthenediones in water
  作者：Mazaahir Kidwai、Arti Jain

  DOI：10.1002/aoc.2895

  日期：2012.10

  An efficient route for the condensation of aldehydes with dimedone in the presence of Zn[(L)Proline]2 in water has been reported. Hydrophilicity of the catalyst is the main attribute of this reaction. The water‐mediated reaction using catalytic amounts of recyclable catalyst avoids the use of expensive, corrosive reagents and toxic solvents and provides operational simplicity. Moreover, column chromatography

  已经报道了在水中Zn [（L）脯氨酸] 2存在下醛与二甲酮缩合的有效途径。催化剂的亲水性是该反应的主要属性。使用催化量的可循环催化剂的水介导反应避免了使用昂贵的腐蚀性试剂和有毒溶剂，并简化了操作。此外，由于粗产物本身非常纯净，因此不需要柱色谱和产物重结晶，因此可以用于大规模的目标导向合成。版权所有©2012 John Wiley＆Sons，Ltd.
• An efficient green synthesis of xanthenedione derivatives promoted by acidic ionic liquid
  作者：Jing-Jun Ma、Chun Wang、Qiu-Hua Wu、Ran-Xiao Tang、Hai-Yan Liu、Qing Li

  DOI：10.1002/hc.20486

  日期：2008.9

  Xanthenedione derivatives were prepared through the condensation reaction of aromatic aldehydes with 5,5-dimethyl-1,3-cyclohexanedione promoted by acidic ionic liquid. The reaction time was 20–40 min with the yields between 82.3% and 95.3%. It was shown that the proposed method was fast, high efficient, and environmentally benign. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:609–611, 2008; Published

  由芳香醛与5,5-二甲基-1,3-环己二酮在酸性离子液体促进下缩合反应制备呫吨二酮衍生物。反应时间为 20-40 分钟，产率在 82.3% 和 95.3% 之间。结果表明，所提出的方法快速、高效且对环境无害。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:609–611, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20486