14-(4-hydroxy-3-methoxyphenyl)-14H-dibenzo[a,j]xanthene | 68828-14-8

• 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: 14-(4-hydroxy-3-methoxyphenyl)-14H-dibenzo[a,j]xanthene
• 英文别名: 2-Methoxy-4-(13-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaen-2-yl)phenol
• CAS: 68828-14-8
• 化学式: C₂₈H₂₀O₃
• 分子量: 404.465
• InChiKey: HNPWKUCEUDCACA-UHFFFAOYSA-N

物化性质

• 熔点：
  208-210 °C
• 沸点：
  590.3±50.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dibenzo[a,j]xanthenylium; bromide 在 sodium 2-methoxyphenolate 作用下， 生成 14-(4-hydroxy-3-methoxyphenyl)-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  Proliferating Trichilemmal Cyst: Report of Two Cases, One Benign and the Other Malignant

  摘要：

  AbstractProliferating trichilemmal cyst (PTC) is a rare but morphologically distinct tumor that usually arises on the scalp of elderly women. We report two cases of PTC, one benign and the other malignant. PTCs are well circumscribed, subepidermal lesions and demonstrate a uniform histologic pattern with varying degrees of cytological atypia. Malignant proliferating trichilemmal cyst (MPTC) has features in common with benign proliferating trichilemmal cyst (BPTC), including a central area of abrupt keratinization and hyperplastic squamous epithelium forming solid areas. The diagnosis of MPTC is essentially based on histological features. The presence of a high mitotic rate, atypical mitosis, severe nuclear pleomorphism, and tumor invasion of the adjacent tissues are the essential histological features of malignancy in these unusual tumors. The therapeutic approach in malignant cases is the same as that in the treatment of BPTC: surgical removal with a wide clear margin. However, even with adequate resection, both tumors tend to recur locally.

  DOI：

  10.1111/j.1346-8138.2002.tb00252.x

文献信息

• An efficient and reusable ionic liquid catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions
  作者：Anlian Zhu、Shukun Bai、Wei Jin、Ruixia Liu、Lingjun Li、Yang Zhao、Jianji Wang

  DOI：10.1039/c4ra06521b

  日期：——

  In this work, it was found that acidic protic ionic liquid N,N-dimethylaminoethanol hydrosulfate ([DMEA][HSO4]) was an efficient and reusable catalyst for the one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions. This ionic liquid is very cheap, air and water stable, and can be easily recovered and reused for at least six cycles. The catalytic system described here is

  在这项工作中，发现酸性质子离子液体N，N-二甲基氨基乙醇氢硫酸盐（[DMEA] [HSO 4 ]）是一锅合成14-芳基-14 H-二苯并[ a ]的有效且可重复使用的催化剂。在无溶剂条件下，j ] x吨。这种离子液体非常便宜，对空气和水稳定，并且可以轻松回收并重复使用至少六个循环。这里描述的催化系统是绿色方案，因为在单锅合成14-芳基-14 H-二苯并[ a，jx吨，目标化合物的收率极好，操作和后处理程序简单，没有使用挥发性有机溶剂。提示该离子液体的阳离子与阴离子的协同作用是高催化活性和高化学选择性的主要原因。放大实验还表明该催化体系在工业应用中具有潜力。
• Antimony (III) Acetate as a Versatile and Efficient Catalyst for Synthesis of 14-Aryl-14H-Dibenzo[a,j]Xanthenes at room Temperature
  作者：Fatemeh Hakimi、Alireza Hassanabadi

  DOI：10.3184/174751915x14198609004990

  日期：2015.1

  Antimony (III) acetate was used in the one-pot three-component synthesis of biologically active 14-aryl-14H-dibenzo[a,j] xanthenes from the condensation between arylaldehydes and (3-naphthol under solvent-free conditions at ambient temperature. This methodology has a number of advantages such as, short reaction time, easy work-up and high yields.

  醋酸锑（III）被用于在常温无溶剂条件下，以芳基醛和（3-萘酚）缩合为原料，单锅三组分合成具有生物活性的 14-芳基-14H-二苯并[a,j]呫吨。这种方法具有反应时间短、易于操作和收率高等优点。
• Synthesis of 14-aryl-14<i>H</i>-dibenzo[<i>a,j</i>]xanthene Derivatives Catalysed by Expanded Graphite under Solvent-Free Condition
  作者：Geng-Chen Li

  DOI：10.3184/030823408x340771

  日期：2008.8

  A convenient eco-friendly procedure has been developed for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives by one-pot condensation of 2-naphthol and aryl aldehydes catalysed by expanded graphite under solvent-free conditions. The present methodology offers several advantages such as excellent yields, shorter reaction times, low cost and reusability of the catalyst.

  已经开发了一种方便的环保程序，用于在无溶剂条件下通过膨胀石墨催化的 2-萘酚和芳基醛的一锅缩合合成 14-芳基-14H-二苯并[a,j] 呫吨衍生物。本方法提供了几个优点，例如优异的产率、更短的反应时间、低成本和催化剂的可重复使用性。
• Perchloric Acid–Silica (HClO4⋅SiO2)-Catalyzed Synthesis of 14-Alkyl- or 14-Aryl-14H-dibenzo[a,j]xanthenes andN-[(2-Hydroxynaphthalen-1-yl)methyl]amides
  作者：Biswanath Das、D. Nandan Kumar、Keetha Laxminarayana、B. Ravikanth

  DOI：10.1002/hlca.200790134

  日期：2007.7

  The synthesis of 14-aryl- or 14-alkyl-14H-dibenzo[a,j]xanthenes 3 involving the treatment of naphthalen-2-ol (1) with arenecarboxaldehydes or alkanals 2 in the presence of HClO4⋅SiO2 as a heterogeneous catalyst was achieved (Table 1), and this reaction was extended to the preparation of N-[(2-hydroxynaphthalen-1-yl)methyl]amides 5 by a three-component reaction with urea (4a) or an amide 4b–d as a third

  14芳基-或14-烷基-14的合成ħ -二苯并[一，Ĵ ]呫吨3涉及萘-2-醇（治疗1）配有arenecarboxaldehydes或链烷醛2在高氯酸的存在下4 ⋅SiO 2作为获得了非均相催化剂（表1），并且该反应通过与尿素（4a）或酰胺4b的三组分反应而扩展到N -[（2-羟基萘-1-基）甲基]酰胺5的制备。– d作为第三种反应物（表2）。
• Metal free Lewis acid promoted one-pot synthesis of 14-aryl-14H dibenzo [a,j] xanthenes and their simple biological evolution
  作者：Uppalaiah Kusampally、Ramakanth Pagadala、Chinna Rajanna Kamatala

  DOI：10.1016/j.tetlet.2017.07.037

  日期：2017.8

  A green, competent one-pot synthesis of 14-aryl 14H-dibenzo [a,j] xanthene and its bio-computational studies are reported. Target compounds are prepared by the condensation of 2-naphthol with benzaldehyde and its substituents using metal free benzyltrimethylammonium tribromide (BTMA-Br3) catalyst under solvent free thermal and microwave conditions. This technique has more advantages such as high yield

  报道了绿色的，能胜任的一锅合成14-芳基14 H-二苯并[ a，j ]氧杂蒽及其生物计算研究。使用无金属苄基三甲基三溴化铵（BTMA-Br 3）催化剂，在无溶剂的热和微波条件下，通过将2-萘酚与苯甲醛及其取代基缩合来制备目标化合物。该技术具有更多的优点，例如高收率，清洁的过程，低的反应时间，简单的后处理和温和的路易斯有机酸催化剂。