2-溴-5-甲氧基萘-1,4-二醇 | 107941-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴-5-甲氧基萘-1,4-二醇
• 英文名称: 2-bromo-5-methoxy-1,4-naphthalenediol
• 英文别名: 1,4-Naphthalenediol, 2-bromo-5-methoxy-；2-bromo-5-methoxynaphthalene-1,4-diol
• CAS: 107941-21-9
• 化学式: C₁₁H₉BrO₃
• 分子量: 269.095
• InChiKey: UCQYDPSKLHHUCG-UHFFFAOYSA-N

物化性质

• 沸点：
  425.2±40.0 °C(Predicted)
• 密度：
  1.675±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-5-甲氧基萘-1,4-二醇 在 叔丁基锂 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 25.25h， 生成 2-(hydroxyphenylmethyl)-1,4,5-trimethoxynaphthalene
  参考文献：
  名称：

  Synthetic approach to aklavinone using 2-oxo-2H-pyran-5-carboxylate (coumalate) intermediates

  摘要：

  DOI：

  10.1021/jo00386a002
• 作为产物：
  描述：

  2-bromo-5-hydroxy-[1,4]naphthoquinone 在 sodium dithionate 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 20.17h， 生成 2-溴-5-甲氧基萘-1,4-二醇
  参考文献：
  名称：

  Synthetic approach to aklavinone using 2-oxo-2H-pyran-5-carboxylate (coumalate) intermediates

  摘要：

  DOI：

  10.1021/jo00386a002

文献信息

• Synthesis and biological evaluation of (±)-cryptotanshinone and its simplified analogues as potent CDC25 inhibitors
  作者：Wei Gang Huang、Ying Yan Jiang、Qian Li、Jia Li、Jing Ya Li、Wei Lu、Jun Chao Cai

  DOI：10.1016/j.tet.2004.12.033

  日期：2005.2

  (+/-)-Cryptotanshinone and its simplified analogues were synthesized via SmI2 promoted radical cyclization to construct the furan ring. Analogues 18 and 26 were identified as effective inhibitors of dual specificity protein phosphatase CDC25B which is a key enzyme for cell cycle progression, and they also inhibited growth in A-549 human lung cancer cell line. (C) 2004 Elsevier Ltd. All rights reserved.

  (+/-)-Cryptotanshinone及其简化的类似物通过SmI2促进的自由基环化反应构建了呋喃环，成功实现合成。其中，类似物18和26被鉴定为双特异性蛋白磷酸酶CDC25B的有效抑制剂，而CDC25B是细胞周期进展中的关键酶。此外，这些类似物还能够抑制A-549人肺癌细胞系的生长。(C) 2004 Elsevier Ltd. 保留所有权利。
• Electrocyclic Ring Closure of the Enols of Vinyl Quinones. A <i>2H</i>-Chromene Synthesis
  作者：Kathlyn A. Parker、Thomas L. Mindt

  DOI：10.1021/ol0167199

  日期：2001.11.1

  Thermolysis of enolizable vinyl quinones in polar, aprotic media provides 2H-chromenes. Experimental evidence supports a two-step mechanism in which enolization is followed by a thermal 6pi-electrocyclic reaction of an intermediate quinone methide. Application of this method led to the total synthesis of the reputed structure of an Ageratum juvenile hormone. When enolizable vinyl quinones are the products

  极性非质子介质中可烯化的乙烯基醌的热解可提供2H-色烯。实验证据支持两步机理，其中烯醇化之后是中间体醌甲基化物的热6π-电环反应。该方法的应用导致了香ger子幼体激素的已知结构的全合成。当可烯化的乙烯基醌是斯蒂勒偶联的产物时，可直接获得色烯环化产物。[反应：看文字]
• Synthetic studies on nogalamycin : stereospecific C-5 alkylations of a sugar derivative via claisen rearrangement and a new route to 1,1,4-trialkoxybuta-1,3-dienes
  作者：J.-M. Vatele

  DOI：10.1016/s0040-4020(01)87284-7

  日期：1986.1

  Claisen rearrangement of the 4-methoxybutadienylether of the allylic alcohol 13, which was made in 15 steps from D-glucose, afforded one major aldehyde 17 or 18 in good yield. All attempts to oxidize this aldehyde to an acid were unsuccessful. The model compound 24 and compound 13 were converted respectively to the α ,β -unsaturated esters 25 and 26. Compound 25 was further transformed into the 1,1

  由D-葡萄糖以15个步骤制得的烯丙醇13的4-甲氧基丁二烯基醚的克莱森重排以良好的产率提供了一种主要的醛17或18。将这种醛氧化为酸的所有尝试均未成功。将模型化合物24和化合物13分别转化为α，β-不饱和酯25和26。将化合物25进一步转化为1,1,4-三烷氧基丁-1,3-二烯27，发现其对醌没有反应性。
• Thiolate-mediated reductive cyclization: asymmetric total synthesis of (+)-engelharquinone
  作者：Yoshio Ando、Takumi Fukazawa、Subaru Hori、Ken Ohmori、Keisuke Suzuki

  DOI：10.1080/10426507.2019.1603718

  日期：2019.7.3

  Abstract We report herein the asymmetric total synthesis of (+)-engelharquinone and its epoxide by exploiting two key reactions; (1) Rhodium catalyzed asymmetric 1,4-addition and (2) thiolate-mediated reductive cyclization. Graphical Abstract

  摘要 我们在此报告了 (+)-engelharquinone 及其环氧化物的不对称全合成，利用两个关键反应；(1) 铑催化不对称 1,4-加成和 (2) 硫醇盐介导的还原环化。图形概要
• Convergent synthesis of 2H-chromenes—a formal [3+3] cycloaddition by a one-pot, three-step cascade
  作者：Kathlyn A. Parker、Thomas L. Mindt

  DOI：10.1016/j.tet.2011.09.068

  日期：2011.12

  In cases in which the palladium-catalyzed coupling of a bromoquinone with a vinyl stannane affords a vinyl quinone that enolizes, the resulting ortho-quinone methide undergoes an oxa-6 pi electrocyclization. Enolization is promoted by the presence of a polar additive. The net conversion is a formal [3+3] cycloaddition that gives 2H-chromenes. Because the first two steps of the cascade are catalyzed, the overall conversion is an example of multicatalysis. Yields for the optimized, one-pot protocol are dramatically improved over the conventional stepwise process. (C) 2011 Elsevier Ltd. All rights reserved.