(+/-)-3-ethyl-3,4-dihydroisocoumarin | 26566-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (+/-)-3-ethyl-3,4-dihydroisocoumarin
• 英文别名: 3-ethylisochroman-1-one；3-Ethyl-3,4-dihydroisochromen-1-one
• CAS: 26566-22-3
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: HLHWHUDEMIPRDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(but-1'-enyl)benzoic acid 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(+/-)-3-ethyl-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Novel AlCl₃catalysed syntheses of naturally occurring (±) 8-hydroxy-3-methyl-3,4-dihydroisocoumarins

  摘要：

  用 AlCl3 在二氯甲烷中处理(±) 3-乙基邻苯二甲酸 2 或 2-(丙-1-烯基)苯甲酸 5，可以高产率地得到天然的(±) 8-羟基-3-甲基-3,4-二氢异香豆素 3。

  DOI：

  10.1039/c39920000883

文献信息

• Synthesis of Chiral 3-Alkyl-3,4-dihydroisocoumarins by Dynamic Kinetic Resolutions Catalyzed by a Baeyer−Villiger Monooxygenase
  作者：Ana Rioz-Martínez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1021/jo902519j

  日期：2010.3.19

  Baeyer−Villiger monooxygenases have been tested in the oxidation of racemic benzofused ketones. When employing a single mutant of phenylacetone monooxygenase (M446G PAMO) under the proper reaction conditions, it was possible to achieve 3-substituted 3,4-dihydroisocoumarins with high yields and optical purities through regioselective dynamic kinetic resolution processes.

  Baeyer-Villiger单加氧酶已在外消旋苯并稠合的酮的氧化中进行了测试。当在适当的反应条件下使用单个突变体的苯丙酮单加氧酶（M446G PAMO）时，可以通过区域选择性动态动力学拆分过程以高收率和光学纯度获得3-取代的3,4-二氢异香豆素。
• α-Angelica lactone catalyzed oxidation of benzylic sp³ C–H bonds of isochromans and phthalans
  作者：Thanusha Thatikonda、Siddharth K. Deepake、Pawan Kumar、Utpal Das

  DOI：10.1039/d0ob00729c

  日期：——

  efficient benzylic C–H oxygenations of cyclic ethers using oxygen as an oxidant. This oxidation reaction utilizes α-angelica lactone as a low cost/low molecular weight catalyst. The optimized reaction conditions allow the synthesis of valued isocoumarins and phthalides from readily available precursors in good yields. Mechanistic studies indicate that the reaction pathway likely involves a radical process

  已开发出一种无金属的有机催化系统，用于使用氧气作为氧化剂对环醚进行高效苄基CH氧化。该氧化反应利用α-当归内酯作为低成本/低分子量催化剂。优化的反应条件允许从容易获得的前体以高收率合成有价值的异香豆素和邻苯二甲酸酯。机理研究表明，该反应途径可能涉及通过过氧化物中间体的自由基过程。
• Reductive electrophilic substitution of phthalans and ring expansion to isochroman derivatives
  作者：Ugo Azzena、Salvatore Demartis、Maria Giovanna Fiori、Giovanni Melloni、Luisa Pisano

  DOI：10.1016/0040-4039(95)01692-b

  日期：1995.10

  of a stable aromatic dilithium compound. The adducts of the latter with CO2, aldehydes or ketones undergo ring closure to isochroman derivatives, leading to ring expansion of the original heterocycle. The reductive electrophilic substitution procedure was successfully extended to the substituted phthalans 1b and 1c, to afford the corresponding isochroman-3ones in satisfactory yields.

  在催化量的萘的存在下，邻苯二甲酸1a与锂金属的还原裂解导致形成稳定的芳族二锂化合物。后者与CO 2，醛或酮的加成物闭环成异色满衍生物，导致原始杂环的扩环。还原亲电取代程序已成功地扩展到取代的酞菁1b和1c，以令人满意的产率提供了相应的异色满-3one。
• Fluoroamide-Directed Regiodivergent C-Alkylation of Nitroalkanes
  作者：Zhibin Du、Shiwen Liu、Yuke Li、Junjie Peng、Yanji Sun、Yanshan Song、Yuxuan Liu、Xiaojun Zeng

  DOI：10.1021/acs.orglett.3c01297

  日期：2023.6.30

  Herein, by exploiting different activation modes of fluoroamides, we achieved α- and δ-C(sp3)–H alkylation of nitroalkanes with switchable regioselectivity. Cu catalysis enabled the interception of a distal C-centered radical by a N-centered radical to couple nitroalkanes and unactivated δ-C–H bonds. In addition, imines generated in situ by fluoroamides were trapped by nitroalkanes to realize the α-C–H

  在此，通过利用氟酰胺的不同活化模式，我们实现了具有可切换区域选择性的硝基烷烃的α-和δ-C(sp 3 )–H烷基化。Cu 催化作用使得以 N 为中心的自由基拦截远端以 C 为中心的自由基，从而偶联硝基烷烃和未活化的 δ-C-H 键。此外，氟酰胺原位生成的亚胺被硝基烷烃捕获，实现酰胺的α-C-H烷基化。这两种可扩展的协议都具有广泛的底物范围和良好的官能团耐受性。
• Electron-Transfer-Induced Reductive Cleavage of Phthalans:  Reactivity and Synthetic Applications
  作者：Ugo Azzena、Salvatore Demartis、Giovanni Melloni

  DOI：10.1021/jo9604548

  日期：1996.1.1

  The behavior of phthalan (1a) was investigated under conditions of electron transfer from alkali metals in aprotic solvents. Reaction with lithium in the presence of a catalytic amount of naphthalene in THF led to the reductive cleavage of an arylmethyl carbon-oxygen bond, with formation of a stable dilithium compound. Trapping of this intermediate with several electrophiles (alkyl halides, carbonyl derivatives, CO2) was successful. The extension of this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussed.