2-acetyl-5,8-dimethoxy-naphthalene | 84574-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetyl-5,8-dimethoxy-naphthalene
• 英文别名: 6-Acetyl-1,4-dimethoxynaphthalene；1-(5,8-dimethoxynaphthalen-2-yl)ethanone
• CAS: 84574-25-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: LFUSTHUNVXVXLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C
• 沸点：
  387.2±22.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-5,8-dimethoxy-naphthalene 在 ammonium cerium (IV) nitrate 、 溴 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.83h， 生成 6-(3-ethyl-1,2,4-oxadiazol-5-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  恶二唑取代的萘并[2,3-b]噻吩-4,9-二酮类化合物是角质形成细胞过度增殖的有效抑制剂。三环醌骨架和恶二唑取代基的构效关系。

  摘要：

  合成了恶二唑取代的萘并[2,3-b]噻吩-4,9-二酮的新型类似物，其中三环醌骨架被较简单的部分系统取代，例如结构较少的环和开链形式，而恶二唑环得以维持。另外，探索了原始的1,2,4-恶二唑环的变体。总的来说，完整的三环醌对于有效抑制人角质形成细胞的过度增殖至关重要，而类似的蒽醌则没有活性。而且，恶二唑环本身不足以引起活性。但是，恶二唑环中杂原子位置的重排导致了高效抑制剂，化合物24b是该系列中最有效的类似物，在纳摩尔范围内显示出IC50。此外，

  DOI：

  10.1016/j.ejmech.2017.03.084
• 作为产物：
  描述：

  3-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 作用下， 以90%的产率得到2-acetyl-5,8-dimethoxy-naphthalene
  参考文献：
  名称：

  Simple Synthesis of 2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A Key Intermediate for the Synthesis of 4-Demethoxydaunomycinone

  摘要：

  2-乙酰基-5,8-二甲氧基-3,4-二氢萘是通过将氧化腈与相应的二氢萘进行1,3-二极性环加成反应制备的。

  DOI：

  10.1039/a901526d

文献信息

• Kuendig, E. Peter; Desobry, Vincent; Simmons, Dana P., Journal of the American Chemical Society, 1989, vol. 111, p. 1804 - 1814
  作者：Kuendig, E. Peter、Desobry, Vincent、Simmons, Dana P.、Wenger, Eric

  DOI：——

  日期：——
• Protein tyrosine kinase inhibitory properties of planar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis
  作者：Khisal A. Alvi、Jaime Rodriguez、Maria Cristina Diaz、Robert Moretti、Robert S. Wilhelm、Rita H. Lee、Doris L. Slate、Phillip Crews

  DOI：10.1021/jo00070a023

  日期：1993.8

  Nine related polycyclic quinones and hydroquinones of the halenaquinone class were isolated from two Indo-Pacific collections of the sponge Xestospongia cf. carbonaria. The halenaquinone family appears not to be of polyketide origin but can be biogenetically derived by the union of a sesquiterpene and a quinone. Four new metabolites were characterized including tetrahydrohalenaquinone B (8a), 14-methoxyhalenaquinone (9), xestoquinolide A (10), and xestoquinolide B (11). These were accompanied by five known compounds, halenaquinone (3), halenaquinol (4), halenaquinol sulfate (5), xestoquinone (6), and tetrahydrohalenaquinone A (7a). The new structures were established from 2D NMR data, and the absolute stereochemistry of the chiral centers in 7 and 8 was determined by the formation of 7b and 7c, the bis esters of O-methylmandelic acid. A series of polycyclic models of natural products 3 and 6 were synthesized and included 16-23. The more complex members of this group were assembled via a 4 + 2 cycloaddition between an o-quinodimethane and a functionalized enone. The marine natural products plus two known fungal metabolites, viridin (13) and wortmannin (14), along with halenaquinone synthetic model compounds, were each tested for their ability to inhibit the activity of pp60v-src protein tyrosine kinase (PTK). Halenaquinone and 14-methoxyhalenaquinone were the most potent with IC50 values <10 muM. The other compounds were either less potent or inactive, and a rationalization for this SAR (structure activity relationship) pattern is presented.
• A short synthesis of +− 2-acetyl-5-8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol - a key intermediate for anthracyclinone synthesis
  作者：A.V.Rama Rao、V.H. Deshpande、N.Laxma Reddy

  DOI：10.1016/s0040-4039(00)85604-x

  日期：1982.1
• Thermodynamic control of regioselectivity in the addition of carbanions to (arene)tricarbonylchromium complexes
  作者：E. Peter Kuendig、Vincent Desobry、Dana P. Simmons、Eric Wenger

  DOI：10.1021/ja00187a039

  日期：1989.3
• A solvolytic method for introducing the C-7 hydroxyl group in anthracyclinones: Synthesis of (±)-daunomycinone
  作者：C.Linga Reddy、M. Nagarajan*

  DOI：10.1016/s0040-4039(00)80441-4

  日期：1988.1