4-ethyl-2H-chromen-2-one | 99109-29-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-ethyl-2H-chromen-2-one
• 英文别名: 4-Ethyl-chromen-2-one；4-ethylchromen-2-one
• CAS: 99109-29-2
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: AHGDJNMMWMUTIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-ethyl-2H-chromen-2-one 在 氢氧化钾 、 乙酸乙酯 、 铂 作用下， 生成 3-(2-methoxy-phenyl)-valeric acid
  参考文献：
  名称：

  Cocker et al., Journal of the Chemical Society, 1953, p. 2355,2359

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-2H-苯并吡喃-2-酮 在 吡啶 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.5h， 生成 4-ethyl-2H-chromen-2-one
  参考文献：
  名称：

  Reaction of 3-halogeno-2H-1-benzopyran-2-ones with organometallic compounds. Synthesis of 4-Alkyl-2H-1-benzopyran-2-ones. X-Ray molecular structure of 3-bromo-3,4-dihydro-4-isopropylcoumarin

  摘要：

  3-Halogeno-2H-1-benzopyran-2-ones react with magnesium, lithium, aluminium and copper derivatives to give 3,4-dihydrocoumarins and 3-(o-hydroxyphenyl)propenols as major products. The nature and the ratio of the products in the final mixture depend on the solvent and on the organometallic reagent. Grignard derivatives yield 1,4-monoalkylation compounds in tetrahydrofuran (THF) or 1,2-dialkylation derivatives in toluene. In some cases the dehalogenation competes with the 1,2-alkylation process in the reactions with alkyllithiums. The presence of the halogen at C-3 increases the reductive ability of organoaluminiums. In general, the reaction with lithium dialkylcuprates leads to complex mixtures of products. The 4-alkyl-3-halogeno-3,4-dihydrocoumarins obtained undergo dehydrohalogenation easily, and lead to 4-alkylcoumarins in good yields. The tandem alkylation-dehydrohalogenation of 3-halogeno-2H-1-benzopyran-2-ones constitutes a versatile synthesis of 4-alkylcoumarins.

  DOI：

  10.1039/p19910000203

文献信息

• Inhibitors of Hepatitis C Virus
  申请人：D'Andrea Stanley

  公开号：US20080107625A1

  公开（公告）日：2008-05-08

  Macrocyclic peptides are disclosed having the general formula: wherein R 3 , R 3 ′, R 4 , R 6 , R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  揭示了具有一般公式的大环肽： 其中描述了R3、R3'、R4、R6、R'、X、Q和W。还公开了包含这些化合物的组合物以及使用这些化合物抑制HCV的方法。
• Hepatitis C virus inhibitors
  申请人：D'Andrea Stanley

  公开号：US20070099825A1

  公开（公告）日：2007-05-03

  Macrocyclic peptides are disclosed having the general formula: wherein R′, R 3 , R 3′ , R 4 , R 6 , X, Q, and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  大环肽被公开，具有一般的公式： 其中R'，R3，R3'，R4，R6，X，Q和W被描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
  作者：Bin Zhao、Bo Xu

  DOI：10.1039/d0ob02417a

  日期：——

  coumarin derivatives via a tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives

  我们已经通过肉桂酸的串联双键异构化/氧化环化开发了一种香豆素衍生物的有效光催化合成方法。廉价，稳定的x吨酮用作光催化剂，易购的Selectfluor用作氧化剂。该方法可耐受各种官能团，并且通常可提供出色的化学收率。此外，肉桂酸酯的光催化氧化环化得到二聚的木脂素型产物。
• <i>anti</i>-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis
  作者：Javier Corpas、Pablo Mauleón、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1021/acs.orglett.0c02281

  日期：2020.8.21

  electron-poor and electron-rich aryl reagents is reported. This selectivity is achieved through a sequential syn-carbopalladation of the alkyne by an Ar–Pd species, followed by a tandem, Ir-photocatalyzed, counter-thermodynamic E → Z isomerization. The use of ortho-substituted boronic acids enables direct access to pharmaceutically relevant heterocyclic cores via a cascade process. Mechanistic insight

  据报道，与贫电子和富电子芳基试剂均兼容的缺电子内部炔烃的一般催化抗氢芳基化反应。这种选择性是通过Ar-Pd分子对炔烃进行顺式羰基缩合，然后进行Ir串联的Ir光催化逆热力学E → Z异构化来实现的。邻取代的硼酸的使用使得能够经由级联过程直接进入药学上相关的杂环核。提供了有关Ar–Pd与Pd–H作为活性物种参与的机理的见解。
• A novel synthesis of coumarins employing triphenyl(α-carboxymethylene)phosphorane imidazolide as a C-2 synthon
  作者：Puspesh K. Upadhyay、Pradeep Kumar

  DOI：10.1016/j.tetlet.2008.10.133

  日期：2009.1

  A novel one-pot synthesis of coumarins via intramolecular Wittig cyclization from the reaction of phenolic compounds containing ortho-carbonyl group and triphenyl(α-carboxymethylene)phosphorane imidazolide is described.

  描述了一种新的一锅法合成香豆素的方法，该方法是通过分子内的维蒂希环化反应从含有邻羰基的酚类化合物与三苯基（α-羧甲基）正膦亚胺基咪唑化物的反应中合成的。