5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-ol | 865070-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-ol
• 英文别名: 5-methoxy-1-methyl-3,4-dihydro-2H-naphthalen-1-ol
• CAS: 865070-96-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: HAMQZRUIUSVJMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.5±37.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-ol 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 monoisopropylcamphenylborane 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 顺-(+)-5-甲氧基-1-甲基-2-(二正丙基氨基)萘满马来酸
  参考文献：
  名称：

  A short and efficient asymmetric synthesis of (1S,2R)-(+)-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232)

  摘要：

  A general practical asymmetric synthesis of (1S,2R)-(+)-5-methoxyl-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232) was developed in a short and efficient method in high optical purity starting from commercially available 5-methoxy-1-tetralone. Asymmetric hydroboration of 5-methoxy-1-methyl-3,4-dihydronaphthalene with monoisopinocampheylborane followed by treatment with NaOH/H2O2 afforded key intermediate tetrahydronaphthol 4. Compound 4 was converted to the target molecule 1 using straightforward reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00333-x
• 作为产物：
  描述：

  甲基碘化镁 、 5-甲氧基-3,4-二氢-2H-1-萘酮 以 乙醚 为溶剂， 反应 1.0h， 生成 5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-ol
  参考文献：
  名称：

  通过围环闭合轻松构建 oxaphenalene 骨架。曼索酮 F 的形式合成

  摘要：

  通过萘酚醚的易周环闭合有效地构建 oxaphenalene 骨架，以及从容易获得的 5-甲氧基-1-四氢萘酮开始的环化前体的有效制备采用钯诱导的萘酚芳构化。

  DOI：

  10.1039/b001859g

文献信息

• [EN] NEO-TANSHINLACTONE AND ANALOGS AS POTENT AND SELECTIVE ANTI-BREAST CANCER AGENTS<br/>[FR] PUISSANTS ANTICANCEREUX SELECTIFS (CANCER DU SEIN) A BASE DE NEO-TANSHINLACTONE ET ANALOGUES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2005087225A1

  公开（公告）日：2005-09-22

  Compounds of Formulae (I-II) are described : along with methods of using such compounds for the treatment of cancer and pharmeutical formulations thereof.

  化合物的公式（I-II）被描述：以及使用这些化合物治疗癌症的方法和药物配方。
• Criegee rearrangement of α-alkoxy hydroperoxides a synthesis of esters and lactones that complements the baeyer-villiger oxidation of ketones
  作者：Stuart L. Schreiber、Wai-Fong Liew

  DOI：10.1016/s0040-4039(00)81926-7

  日期：1983.1

  α-Alkoxy hydroperoxides undergo Criegee rearrangement upon treatment with (CH3CO)2O to provide esters or lactones.

  用（CH 3 CO）2 O处理后，α-烷氧基氢过氧化物会进行Criegee重排，以提供酯或内酯。
• NEO-TANSHINLACTONE AND ANALOGS AS POTENT AND SELECTIVE ANTI-BREAST CANCER AGENTS
  申请人：Lee Kuo-Hsiung

  公开号：US20090118356A1

  公开（公告）日：2009-05-07

  Compounds of Formulas I-II are described, along with methods of using such compounds for the treatment of cancer and pharmaceutical formulations thereof.

  描述了I-II式化合物，以及使用这些化合物治疗癌症和制备制药配方的方法。
• Synthesis of Some Substituted Naphthalenes as Potential Intermediates for Polyethers and Terpenoids
  作者：A. K. Banerjee、P. S. Poon、M. S. Laya、J. A. Azocar

  DOI：10.1023/b:rugc.0000018662.02489.8d

  日期：2003.11

  1-Benzyloxy-5-hydroxynaphthalene and 1,6-dimethyl-5-hydroxynaphthalene were prepared from 5-methoxy-alpha-tetralone. 6-Methoxy-alpha-tetralone was converted to 1,6-dimethoxy-2-isopropylnaphthalene.
• Antitumor Agents. 239. Isolation, Structure Elucidation, Total Synthesis, and Anti-Breast Cancer Activity of Neo-tanshinlactone from <i>Salvia </i><i>m</i><i>iltiorrhiza</i>
  作者：Xihong Wang、Kenneth F. Bastow、Chang-Ming Sun、Yun-Lian Lin、Hsi-Jung Yu、Ming-Jaw Don、Tian-Shung Wu、Seikou Nakamura、Kuo-Hsiung Lee

  DOI：10.1021/jm040112r

  日期：2004.11.1

  Neo-tanshinlactone (1) was isolated and synthesized for the first time and evaluated in vitro against several human cancer cell lines. Compound 1 showed significant inhibition against two ER+ human breast cancer cell lines and was 10-fold more potent and 20-fold more selective as compared to tamoxifen citrate. Compound 1 also potently inhibited an ER-, HER-2 overexpressing breast cancer cell line. Therefore, this novel compound merits further development as an anti-breast cancer drug candidate.