3-chloro-2-(prop-2-en-1-yloxy)benzaldehyde | 1106304-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-chloro-2-(prop-2-en-1-yloxy)benzaldehyde
• 英文别名: 2-(allyloxy)-3-chlorobenzaldehyde；3-Chloro-2-prop-2-enoxybenzaldehyde；3-chloro-2-prop-2-enoxybenzaldehyde
• CAS: 1106304-55-5
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: MVIZTOKMYCKXTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(prop-2-en-1-yloxy)benzaldehyde 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 [Ru(H)(Cl)(CO)(PCy3)2] 、 乙烯氧基三甲基硅烷 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 对二甲苯 为溶剂， 反应 12.34h， 生成 7-chloro-3-[(trimethylsilyl)methyl]-2-vinyl-1-benzofuran
  参考文献：
  名称：

  Cycloisomerization between Aryl Enol Ether and Silylalkynes under Ruthenium Hydride Catalysis: Synthesis of 2,3-Disubstituted Benzofurans

  摘要：

  Metal-catalyzed cycloisomerization reactions of 1,n-enynes have become conceptually and chemically attractive processes in the search for atom economy, which is. a key subject of current research. However, metal-catalyzed cycloisomerization between aryl enol ether and silylalkynes has not been developed. The ruthenium hydride complex catalyzed cycloisomerization between aryl enol ether and silylalkynes is reported to give benzofurans having useful functional groups, vinyl and trimethylsilylmethyl, on the 2- and 3-positions, respectively.

  DOI：

  10.1021/acs.orglett.7b00985
• 作为产物：
  描述：

  (3-Chloro-2-prop-2-enoxyphenyl)methanol 在 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到3-chloro-2-(prop-2-en-1-yloxy)benzaldehyde
  参考文献：
  名称：

  Copper Catalyzed Selective Oxidation of Benzyl Alcohol to Benzaldehyde

  摘要：

  DOI：

  10.5012/jkcs.2012.56.5.539

文献信息

• Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones
  作者：Hao Hu、Xiaolan Chen、Kai Sun、Junchao Wang、Yan Liu、Hui Liu、Lulu Fan、Bing Yu、Yuanqiang Sun、Lingbo Qu、Yufen Zhao

  DOI：10.1021/acs.orglett.8b02627

  日期：2018.10.5

  A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2–CH═CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds

  一种新颖且方便的银催化自由基级联环化反应，形成多种多样的含苯并二氢吡喃-4-酮，茚满酮或2,3-二氢喹啉-4（1 H）-的1,5- / 1,3-二羰基杂环部分被开发，通过各种2官能苯甲醛，包括2-烯丙氧基苯甲醛，2-烯丙基苯甲醛，和2-N（Ts）的CH反应2 -CH = CH 2取代的苯甲醛，在存在1,3-二羰基化合物AgNO 3 / K 2 S 2 O 8的在温和的反应条件下放入一锅中。新获得的含1,5- / 1,3-二羰基的杂环进一步直接用于合成结构上更多样化的多杂环，主要包括色吡啶和含异恶唑或吡唑的苯并二氢吡喃-4-酮。
• Copper-catalyzed synthesis of CN-containing chroman-4-ones via intramolecular radical cascade acyl-cyanation reaction
  作者：Liang Wang、Min Jiang、Ming-qi Shi

  DOI：10.1016/j.tetlet.2021.153061

  日期：2021.5

  A copper-catalyzed intramolecular radical cascade acyl-cyanation to synthesize cyano-containing chroman-4-ones has been developed. A series of CN-substituted chroman-4-one derivatives can be prepared with moderate to good yields using green cyano source under mild conditions. Control experiments indicated this reaction involved an intramolecular acyl radical addition/cyanation process. Moreover, this

  已经开发了铜催化的分子内自由基级联酰基氰化以合成含氰基的chroman-4-ones。使用绿色氰基源，在温和的条件下，可以中等到良好的产率制备一系列CN取代的chroman-4-one衍生物。对照实验表明该反应涉及分子内酰基自由基加成/氰化过程。此外，该协议具有步长和原子经济性，将氰基引入到chroman-4-one中引起了极大的兴趣和重要性。
• Synthesis of chroman-4-one and indanone derivatives via silver catalyzed radical ring opening/coupling/cyclization cascade
  作者：Qiang Liu、Guanqun Xie、Qiang Wang、Zhendong Mo、Chen Li、Shujiang Ding、Xiaoxia Wang

  DOI：10.1016/j.tet.2019.130490

  日期：2019.10

  conveniently synthesized from readily available cyclopropanols and alkenyl aldehydes via a silver catalyzed radical ring-opening/coupling/cyclization cascade. The reaction proceeded under mild and neutral conditions with broad substrate scope and afforded the desired products in moderate to good yields. A probable mechanism for the cascade reaction was also proposed.

  经由银催化的自由基开环/偶联/环化级联反应，容易地从容易获得的环丙醇和烯基醛合成了多种苯并吡喃-4-酮和茚满酮衍生物。反应在温和和中性条件下，在宽范围的底物范围内进行，并以中等至良好的产率提供了所需的产物。还提出了级联反应的可能机理。
• Hypervalent iodine mediated radical cyclization of o-(allyloxy)arylaldehydes and N-hydroxyphthalimide (NHPI) under metal-free conditions
  作者：De-Mao Chen、Yuan-Yuan Sun、Qing-Qing Han、Zu-Li Wang

  DOI：10.1016/j.tetlet.2020.152482

  日期：2020.11

  chroman-4-ones was developed. The corresponding products can be obtained with moderate to high yields at room temperature. Control experiments suggested that this transformation was likely to proceed via a radical pathway. The preliminary activity test showed that some of the compounds had moderate to high antibacterial activity.

  开发了一种高效，实用的取代苯并吡喃-4-酮的合成方法。可以在室温下以中等至高产率获得相应的产物。对照实验表明，这种转化很可能通过自由基途径进行。初步活性测试表明，某些化合物具有中等至较高的抗菌活性。
• Design, synthesis and decoration of molecular scaffolds for exploitation in the production of alkaloid-like libraries
  作者：Philip Craven、Anthony Aimon、Mark Dow、Nicolas Fleury-Bregeot、Rachel Guilleux、Remy Morgentin、Didier Roche、Tuomo Kalliokoski、Richard Foster、Stephen P. Marsden、Adam Nelson

  DOI：10.1016/j.bmc.2014.12.048

  日期：2015.6

  The design, synthesis and decoration of six small molecule libraries is described. Each library was inspired by structures embedded in the framework of specific alkaloid natural products. The development of optimised syntheses of the required molecular scaffolds is described, in which reactions including Pd-catalysed aminoarylation and diplolar cycloadditions have been exploited as key steps. The synthesis

  描述了六个小分子文库的设计，合成和修饰。每个图书馆的灵感都来自嵌入特定生物碱天然产物框架的结构。描述了所需分子支架的优化合成方法的开发，其中已将包括Pd催化的氨基芳基化和双齿环加成在内的反应用作关键步骤。还描述了所选择的示例性筛选化合物的合成。在五种情况下，库随后根据验证工作的范围和局限性以及预测的分子特性被提名用于生产。总的来说，这项研究成功地合成了超过2500种新型生物碱样化合物，并将其添加到了筛选馆藏中（欧洲联合化合物库，