3-(2,5-dimethoxyphenyl)prop-2-yn-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2,5-dimethoxyphenyl)prop-2-yn-1-ol
• 英文别名: 3-(2,5-Dimethoxy-phenyl)-prop-2-yn-1-ol
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: CJHFYEJQEHGHEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,5-dimethoxyphenyl)prop-2-yn-1-ol 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以99 %的产率得到2-(3-bromoprop-1-yn-1-yl)-1,4-dimethoxybenzene
  参考文献：
  名称：

  applanatumol A的全合成

  摘要：

  applanatumol A 的首次全合成以高度立体控制的方式实现。合成方法包括通过会聚Fráter-Seebach烷基化组装连续的手性中心，通过分子内羟醛反应构建七元环，以及立体选择性串联环化形成四环骨架。

  DOI：

  10.1039/d3cc01997g
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基苯 、 2-丙炔-1-醇 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁胺 作用下， 以86 %的产率得到3-(2,5-dimethoxyphenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  applanatumol A的全合成

  摘要：

  applanatumol A 的首次全合成以高度立体控制的方式实现。合成方法包括通过会聚Fráter-Seebach烷基化组装连续的手性中心，通过分子内羟醛反应构建七元环，以及立体选择性串联环化形成四环骨架。

  DOI：

  10.1039/d3cc01997g

文献信息

• Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers
  作者：Marion A. Franks、Edward A. Schrader、E. Christine Pietsch、Daniel R. Pennella、Suzy V. Torti、Mark E. Welker

  DOI：10.1016/j.bmc.2004.12.037

  日期：2005.3

  A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone

  通过炔丙基醇与芳族卤化物的Sonogashira偶联已经制备了许多炔醇。然后进行螯合控制的有机金属亲核试剂向这些炔醇的添加，然后添加硫亲电试剂，二氧化硫或亚硫酰氯。该方法学用于制备许多氧杂硫基氧化物，这些氧化物已被筛选为NQO1（醌氧化还原酶）诱导剂。
• Total synthesis of MS-444: A myosin light chain kinase and HuR inhibitor from Micromonospora sp. KY7123
  作者：Yan Huang、Jian Wang、Jiazhu Li、Zhen Zhang、Jin-Chun Chen

  DOI：10.1016/j.tetlet.2021.153328

  日期：2021.9

  MS-444, as a myosin light chain kinase and HuR inhibitor, plays an important role in physiological regulation. An alternative total synthesis of MS-444 is reported by a route incorporating Sonogashira coupling, addition/elimination of allenic sulfonium salts generated in situ and intramolecular Friedel-Crafts acylation. This approach starts from commercially available materials and involves a distinctive

  MS-444 作为肌球蛋白轻链激酶和 HuR 抑制剂，在生理调节中起重要作用。MS-444 的另一种全合成是通过结合 Sonogashira 偶联、添加/消除原位生成的丙二烯锍盐和分子内 Friedel-Crafts 酰化的途径报道的。这种方法从市售材料开始，并涉及构建呋喃环的独特方法。该路线中的大部分反应易于实施，具有大规模应用的前景。
• Synthesis of Bioactive Speciosins G and P from <i>Hexagonia speciosa</i>
  作者：Guillermo A. Guerrero-Vásquez、Nuria Chinchilla、José M. G. Molinillo、Francisco A. Macías

  DOI：10.1021/np500341q

  日期：2014.9.26

  The first total synthesis of speciosins P and G, previously isolated from Hexagonia speciosa, is reported. These compounds have been synthesized by Sonogashira coupling from readily available starting materials. Siccayne was also synthesized from the same starting material in two steps along with a number of other derivatives. The compounds were tested in the wheat coleoptile bioassay. The most active compound was the intermediate 18, followed by 29 and 17. The structural requirements for activity in these compounds are the presence of methoxy groups in the aromatic ring and a formyl or hydroxy group in the side chain.
• Exploration of Braverman Reaction Chemistry. Synthesis of Tricyclic Dihydrothiophene Dioxide Derivatives from Bispropargyl Sulfones
  作者：Ken S. Feldman、Brandon R. Selfridge

  DOI：10.3987/com-09-11840

  日期：——

  The base-mediated bicyclization Of unsymmetrical bispropargyl sulfones furnishes varying yields of dihydroisobenzothiophene dioxides through a presumed diradical intermediate. Attempts to trap a putative thiophene dioxide intermediate via Diels-Alder reaction with a pendant alkyne were not successful.
• Total synthesis of applanatumol A
  作者：Kyohei Uchida、Yuichiro Kawamoto、Toyoharu Kobayashi、Hisanaka Ito

  DOI：10.1039/d3cc01997g

  日期：——

  The first total synthesis of applanatumol A has been achieved in a highly stereocontrolled manner. The synthetic method includes assembly of the contiguous chiral centers by convergent Fráter–Seebach alkylation, construction of the seven-membered ring by intramolecular aldol reaction, and stereoselective tandem cyclization to form the tetracyclic skeleton.

  applanatumol A 的首次全合成以高度立体控制的方式实现。合成方法包括通过会聚Fráter-Seebach烷基化组装连续的手性中心，通过分子内羟醛反应构建七元环，以及立体选择性串联环化形成四环骨架。