1,1-二甲基-5-四氢萘酚 | 171979-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 1,1-二甲基-5-四氢萘酚
• 英文名称: 1,1-dimethyl-5-tetralol
• 英文别名: 1,1-Dimethyl-tetralol-(5)；5,5-dimethyl-7,8-dihydro-6H-naphthalen-1-ol
• CAS: 171979-69-4
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: RIAUQNNBRKWTBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-二甲基-5-四氢萘酚 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 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -78.0~90.0 ℃ 、344.73 kPa 条件下， 反应 132.5h， 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 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.75h， 生成 1,1-二甲基-5-四氢萘酚
  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

• 2,3-二氢萘并[2,3-b]呋喃-4,9-二酮类化合物及其制备方法和用途
  申请人：中国医学科学院药物研究所

  公开号：CN111825644B

  公开（公告）日：2023-07-28

  本发明提供了2,3‑二氢萘并[2,3‑b]呋喃‑4,9‑二酮类化合物及其制备方法和用途，属于医药技术领域。具体提供了如通式I‑A和I‑B所示的2,3‑二氢萘并[2,3‑b]呋喃‑4,9‑二酮类化合物，含有这类化合物的药物组合物，这类化合物的制备方法。本发明化合物具有STAT3抑制活性，能用于制备治疗和/或预防与STAT3活性相关的疾病药物，所述的疾病包括多种癌症，例如乳腺癌、肺癌、口腔癌、肾癌、食道癌、肝癌、胃癌、肠癌、宫颈癌以及卵巢癌等。
• 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。
• [EN] CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] DERIVES DE CHROMENE A TITRE D'AGENTS ANTI-INFLAMMATOIRES
  申请人：PHARMACIA CORP

  公开号：WO2004087687A1

  公开（公告）日：2004-10-14

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.

  该发明涉及在治疗与环氧合酶-2介导的疾病相关的情况中具有效用的方法和化合物。特别感兴趣的化合物是由式(I)定义的苯并吡喃和它们的类似物。其中Z、X、R1、R2、R3和R4如规范中所述。
• Novel 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole compounds
  申请人：——

  公开号：US20020002161A1

  公开（公告）日：2002-01-03

  Certain 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indoles are 5-HT ligands and are useful for treating diseases wherein modulation of 5-HT activity is desired.

  某些2,3,4,5-四氢-1H-[1,4]二氮杂丁[1,7-a]吲哚化合物是5-HT受体配体，并且可用于治疗需要调节5-HT活性的疾病。
• Total synthesis of tanshinone IIA
  作者：He Huang、Chuanjun Song、Zhen Wang、Mengyang Li、Junbiao Chang

  DOI：10.1016/j.tetlet.2020.152102

  日期：2020.7

  A novel synthetic route toward tanshinone IIA has been developed. Key steps involve a base mediated furan ring formation, and an acyloin condensation reaction to construct the ortho-quinone ring.

  已经开发出一种新颖的丹参酮IIA合成途径。关键步骤涉及碱基介导的呋喃环的形成，以及酰基环缩合反应以构建邻醌环。