9-(p-tolyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 446309-51-9

• 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-(p-tolyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-methylphenyl)-1,8-dioxo-octahydroxanthene；9-(4-methylphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；9-(4-methylphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 446309-51-9
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: PLSVXUNGVSQDOE-UHFFFAOYSA-N

物化性质

• 熔点：
  216-218 °C(Solv: ethanol (64-17-5))
• 沸点：
  514.4±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-(p-tolyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 氯磺酸 作用下， 以 乙醇 为溶剂， 生成 5-(1,8-Dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)-2,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：

  对甲基苯甲醛 在 哌啶 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 生成 9-(p-tolyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-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

• Molybdate sulfonic acid: preparation, characterization, and application as an effective and reusable catalyst for octahydroxanthene-1,8-dione synthesis
  作者：Bahador Karami、Zahra Zare、Khalil Eskandari

  DOI：10.2478/s11696-012-0263-y

  日期：2013.1.1

  Molybdate sulfonic acid (MSA) as a highly efficient catalyst was synthesized and employed for the synthesis of octahydroxanthene-1,8-dione derivatives. MSA efficiently catalyzed condensation of a wide range of aryl aldehydes and cyclohexane-1,3-diones to obtain octahydroxanthene-1,8-diones. It was characterized by X-ray fluorescence (XRF), X-ray diffraction (XRD), and FT-IR spectroscopy. This catalyst

  合成了作为高效催化剂的钼酸磺酸（MSA），并用于合成八氢氧杂蒽-1,8-二酮衍生物。MSA有效地催化了各种芳基醛与环己烷-1,3-二酮的缩合反应，从而得到八氢氧杂蒽-1,8-二酮。它的特征在于X射线荧光（XRF），X射线衍射（XRD）和FT-IR光谱。该催化剂可以回收并在其他反应中重复使用几次，以保持其高活性。这种新颖且绿色的方法非常便宜，并具有许多优点，例如产率高，使用可回收且环保的催化剂以及后处理程序简单。
• 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。
• Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: a new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions
  作者：Ali Amoozadeh、Salman Rahmani、Mehrnoosh Bitaraf、Fatemeh Bolghan Abadi、Elham Tabrizian

  DOI：10.1039/c5nj02430g

  日期：——

  Nano-zirconia-supported sulfonic acid as a novel, highly efficient and recyclable heterogeneous nanocatalyst is reported for the synthesis of multicomponent reactions.

  报告了一种新型的、高效的、可回收的纳米催化剂——纳米氧化锆支撑的磺酸，用于合成多组分反应。

• A New Access to 1,8-Dioxooctahydroxanthenes Using Yttrium(III) Nitrate Hexahydrate and Tin(II) Chloride Dihydrate as Effective and Reusable Catalysts
  作者：B. Karami、K. Eskandari、Z. Zare、S. Gholipour

  DOI：10.1007/s10593-014-1423-5

  日期：2014.3

  environmentally adapted synthesis of xanthene derivatives by condensation of a wide range of aryl aldehydes and cyclohexane-1,3-diones in the presence of catalytic amounts of yttrium(III) nitrate hexahydrate and tin(II) chloride dihydrate is demonstrated.

  在催化量的硝酸钇（III）六水合物和氯化锡（II）二水合物存在下，通过广泛的芳基醛和环己烷-1,3-二酮的缩合，可以高效，环保地合成x吨衍生物。
• Magnetic Fe–Cr–Ni oxide alloy nano-belts prepared from the chemical decomposition of a stainless steel screw (a top-down approach): an efficient and cheap catalyst for multicomponent reactions
  作者：Milad Kazemnejadi、Zeinab Sharafi、Boshra Mahmoudi、Atefeh Zeinali、Mohammad Ali Nasseri

  DOI：10.1007/s13738-019-01814-z

  日期：2020.4

  A new, cheap, and accessible method has been used for the preparation of nano-belts from the chemical decomposition (top-down approach) of a cheap stainless steel screw and found as an efficient magnetically recyclable nanocatalyst for the preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild reaction conditions. The nano-belts, Fe–Cr–Ni oxide alloy, was prepared in a two-step synthesis and characterized with various instrumental methods. Due to magnetic property of the screw (a ferritic-alloy), the resultant nano-belts is magnetic. Magnetic Fe–Cr–Ni alloy nano-belts were applied toward efficient preparation of quinolines and 1,8-dioxo-octahydroxanthenes under mild conditions. The catalyst could be readily recovered and recycled for several consecutive runs, while it suffers from a very low metal leaching and subsequently efficiency drop.

  一种新的、廉价且易得的方法已被用于从廉价不锈钢螺丝的化学分解（自上而下的方法）中制备纳米带，并发现其在温和反应条件下作为高效的磁性可回收纳米催化剂，用于喹啉和1,8-二氧杂-八氢氧杂蒽的制备。这种纳米带，即Fe–Cr–Ni氧化物合金，是通过两步合成法制备的，并使用多种仪器方法进行了表征。由于螺丝（一种铁素体合金）的磁性特性，所得纳米带也具有磁性。磁性Fe–Cr–Ni合金纳米带在温和条件下被应用于高效制备喹啉和1,8-二氧杂-八氢氧杂蒽。该催化剂可以轻易地回收并在多次连续运行中循环使用，同时金属溶出现象极少，因此催化效率几乎不会下降。