1,2,3,4-四氢-5-甲氧基-1,1-二甲基萘 | 33214-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 1,2,3,4-四氢-5-甲氧基-1,1-二甲基萘
• 英文名称: 1,1-dimethyl-5-methoxytetralin
• 英文别名: 5-Methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene；8-methoxy-4,4-dimethyl-2,3-dihydro-1H-naphthalene
• CAS: 33214-70-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: CJNVZUXCGXPSND-UHFFFAOYSA-N

物化性质

• 沸点：
  277.5±29.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-5-甲氧基-1,1-二甲基萘 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 4-二甲氨基吡啶 、 三氟乙酸2,2,2-三氟乙酯 、 4 A molecular sieve 、 硫酸 、 2,4-di-t-butyl-3-methyl phenol 、 四丁基氟化铵 、 氧气 、 四甲基锡 、 三溴化硼 、 三乙胺 、 甲烷磺酰基叠氮化物 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -78.0~90.0 ℃ 、344.73 kPa 条件下， 反应 136.5h， 生成 隐丹参酮
  参考文献：
  名称：

  Aromatic Annulation Strategy for the Synthesis of Angularly-Fused Diterpenoid Quinones. Total Synthesis of (+)-Neocryptotanshinone, (-)-Cryptotanshinone, Tanshinone IIA, and (.+-.)-Royleanone

  摘要：

  The application of a photochemical aromatic annulation strategy in highly efficient total syntheses of several diterpenoid quinones isolated from the traditional Chinese medicine Dan Shen is reported. The pivotal step in each synthesis involves the assembly of a key tricyclic intermediate via the application of a recently developed ''second-generation'' photochemical aromatic annulation method for the construction of highly substituted aromatic systems. In the total synthesis of neocrypto-tanshinone,;the synthesis of the requisite diazo ketone annulation substrate 7 was achieved using palladium-mediated coupling reactions and an intramolecular Friedel-Crafts cyclization to form key carbon-carbon bonds. The pivotal aromatic annulation reaction was then accomplished by irradiating a solution of the diazo ketone 7 and the readily available siloxyalkyne 6 in benzene at room temperature. The desired tricyclic phenol 16 was produced in 58-65% yield and was then converted to (+)-neocryptotanshinone (1) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen. Cyclization to generate (-)-cryptotanshinone (2) was accomplished in high yield by brief exposure of 1 to an ethanolic solution of concentrated sulfuric acid, and dehydrogenation of 2 with DDQ furnished tanshinone IIA (3). As a further demonstration of the utility of the photochemical aromatic annulation strategy in the construction of angularly-fused diterpenes, the total synthesis of(+/-)-royleanone (4) was also investigated. Irradiation of a solution of the diazo ketone 18 and siloxyalkyne 25 produced the tricyclic intermediate 26, which was converted in two steps to royleanone by desilylation and oxidation.

  DOI：

  10.1021/jo00131a006
• 作为产物：
  描述：

  5-溴-2-甲基-2-戊烯 在 正丁基锂 、 三氯化铝 、 四甲基乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.75h， 生成 1,2,3,4-四氢-5-甲氧基-1,1-二甲基萘
  参考文献：
  名称：

  Aromatic Annulation Strategy for the Synthesis of Angularly-Fused Diterpenoid Quinones. Total Synthesis of (+)-Neocryptotanshinone, (-)-Cryptotanshinone, Tanshinone IIA, and (.+-.)-Royleanone

  摘要：

  The application of a photochemical aromatic annulation strategy in highly efficient total syntheses of several diterpenoid quinones isolated from the traditional Chinese medicine Dan Shen is reported. The pivotal step in each synthesis involves the assembly of a key tricyclic intermediate via the application of a recently developed ''second-generation'' photochemical aromatic annulation method for the construction of highly substituted aromatic systems. In the total synthesis of neocrypto-tanshinone,;the synthesis of the requisite diazo ketone annulation substrate 7 was achieved using palladium-mediated coupling reactions and an intramolecular Friedel-Crafts cyclization to form key carbon-carbon bonds. The pivotal aromatic annulation reaction was then accomplished by irradiating a solution of the diazo ketone 7 and the readily available siloxyalkyne 6 in benzene at room temperature. The desired tricyclic phenol 16 was produced in 58-65% yield and was then converted to (+)-neocryptotanshinone (1) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen. Cyclization to generate (-)-cryptotanshinone (2) was accomplished in high yield by brief exposure of 1 to an ethanolic solution of concentrated sulfuric acid, and dehydrogenation of 2 with DDQ furnished tanshinone IIA (3). As a further demonstration of the utility of the photochemical aromatic annulation strategy in the construction of angularly-fused diterpenes, the total synthesis of(+/-)-royleanone (4) was also investigated. Irradiation of a solution of the diazo ketone 18 and siloxyalkyne 25 produced the tricyclic intermediate 26, which was converted in two steps to royleanone by desilylation and oxidation.

  DOI：

  10.1021/jo00131a006

文献信息

• Antitumor agents 269. Non-aromatic ring-A neotanshinlactone analog, TNO, as a new class of potent antitumor agents
  作者：Yizhou Dong、Qian Shi、Kyoko Nakagawa-Goto、Pei-Chi Wu、Kenneth F. Bastow、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2009.09.092

  日期：2009.11

  actone (TNT) and tetrahydronaphthalene-1-ol (TNO) derivatives were designed, synthesized, and evaluated for cytotoxic activity. The TNO derivatives were found to be a promising novel class of in vitro antitumor agents. The cyclohexene ring-A could dramatically affect the antitumor activity and selectivity. Compound 20 showed the highest potency with ED50 values of 0.7 and 1.7 μM against SK-BR-3 and

  设计、合成了四氢新丹参内酯 (TNT) 和四氢萘-1-醇 (TNO) 衍生物，并对其细胞毒活性进行了评估。发现 TNO 衍生物是一种很有前途的新型体外抗肿瘤剂。环己烯环-A 可以显着影响抗肿瘤活性和选择性。化合物20显示出最高的效力，ED 50值分别为 0.7 和 1.7 μM，分别针对 SK-BR-3 和 ZR-75-1 乳腺癌细胞系。
• Biaromatic compounds and pharmaceutical and cosmetic compositions comprising them
  申请人：Galderma Research & Development

  公开号：US06346546B1

  公开（公告）日：2002-02-12

  Biaromatic compounds connected by a propynylene or ailenylene bond, corresponding to the formula (I).

  由丙炔基或芳烃基键连接的双芳香族化合物，对应式（I）。
• 丹参酮ⅡA的新型衍生物及其制备方法和应用
  申请人：中国人民解放军第四军医大学

  公开号：CN106243071A

  公开（公告）日：2016-12-21

  本发明公开了丹参酮ⅡA的新型衍生物及其制备方法和应用，其中，该新型衍生物分子式：C18H20O4，Mass：300.14，结构式：其可以应用在制备抑制胃癌、结肠癌、乳腺癌、肝癌、肺癌等肿瘤的药物中。本发明的有益之处在于：(1)本发明制备得到的新型衍生物能够直接靶向HMGB1，有效抑制多种肿瘤细胞增殖，而且对于正常细胞没有明显影响；(2)制备方法稳定、简捷、易行，制备得到的化合物性质稳定，纯度高。
• Aryl participation in the solvolysis of some gem-dimethyl-substituted 4-aryl-1-alkyl p-bromobenzenesulfonates
  作者：S. Winstein、R. F. Heck

  DOI：10.1021/jo00971a004

  日期：1972.3
• GAMMA SECRETASE MODULATORS
  申请人：Zhu Zhaoning

  公开号：US20100247514A1

  公开（公告）日：2010-09-30

  In its many embodiments, the present invention provides a novel class of heterocyclic compounds as modulators of gamma secretase, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the central nervous system using such compounds or pharmaceutical compositions.