2-(isochroman-1-yl)-1-(4-methoxyphenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(isochroman-1-yl)-1-(4-methoxyphenyl)ethanone
• 英文别名: 2-(3,4-dihydro-1H-isochromen-1-yl)-1-(4-methoxyphenyl)ethanone
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: NYUGKEGAZHCAOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异色满 、 对甲氧基苯乙酮 在 甲烷磺酸 作用下， 以 乙腈 为溶剂， 以71 %的产率得到2-(isochroman-1-yl)-1-(4-methoxyphenyl)ethanone
  参考文献：
  名称：

  异色满与未活化酮的电化学交叉脱氢偶联

  摘要：

  开发了异色满和未活化酮之间前所未有的电化学交叉脱氢偶联反应，可直接合成 α-取代的异色满。该策略为直接激活与异色满的 O 原子相邻的C(sp 3 )-H 键提供了一种简便有效的方法。该方法具有原子经济性高、无化学氧化剂、条件温和等特点，其中甲磺酸（MsOH）既作为电解质又作为催化剂，使该过程更加便捷和环保。抗肿瘤活性化合物的克级实验和合成证明了该协议在实际应用中的巨大潜力。

  DOI：

  10.1021/acs.joc.2c02616

文献信息

• Catalytic amounts of CBr₄ mediated dehydrogenative coupling of isochromans with aromatic ketones
  作者：Congde Huo、Mingxia Wu、Fengjuan Chen、Xiaodong Jia、Yong Yuan、Haisheng Xie

  DOI：10.1039/c4cc09922b

  日期：——

  In the presence of catalytic amounts of CBr₄ (a metal-free mediator), an unexpected oxidative dehydrogenative coupling of isochromans with ketones occurred to construct new C^sp3–C^sp3 bonds. The reactions were performed under simple solvent-free aerobic conditions.

  在存在催化量的CBr₄（一种无金属介质）的情况下，异色酮与酮发生了意外的氧化脱氢偶联反应，构建了新的C^sp3–C^sp3键。这些反应是在简单的无溶剂氧化条件下进行的。
• Structurally Diverse α-Substituted Benzopyran Synthesis through a Practical Metal-Free C(sp³)–H Functionalization
  作者：Wenfang Chen、Zhiyu Xie、Hongbo Zheng、Hongxiang Lou、Lei Liu

  DOI：10.1021/ol503004a

  日期：2014.11.21

  A trityl ion-mediated practical C–H functionalization of a variety of benzopyrans with a wide range of nucleophiles (organoboranes and C–H molecules) at ambient temperature has been disclosed. The metal-free reaction has an excellent functional group tolerance and high chemoselectivity and displays a broad scope with respect to both benzopyran and nucleophile partners, efficiently affording a collection

  已公开了在环境温度下，三苯甲基离子介导的各种苯并吡喃具有广泛的亲核试剂（有机硼烷和CH分子）的C–H实用化方法。不含金属的反应具有出色的官能团耐受性和高化学选择性，并且相对于苯并吡喃和亲核体伙伴均显示出广阔的范围，可高效地一步收集一系列具有多种骨架和α-官能度的苯并吡喃。
• Copper(II) catalyzed cross-dehydrogenative coupling of cyclic benzylic ethers with simple carbonyl compounds by Na2S2O8
  作者：Xinhui Pan、Qingwen Hu、Wenfang Chen、Xigong Liu、Bin Sun、Zhouli Huang、Ziyu Zeng、Liguo Wang、Dan Zhao、Mei Ji、Lei Liu、Hongxiang Lou

  DOI：10.1016/j.tet.2014.03.074

  日期：2014.5

  Copper(II) catalyzed cross-dehydrogenative coupling of cyclic benzylic ethers with a variety of simple carbonyl compounds mediated by Na2S2O8 is developed. The scope of carbonyl components is broad, including simple aldehydes as well as ketones. The use of Na2S2O8 as the oxidant for the CDC reaction is attractive based on economical and environmental factors.

  开发了铜（II）催化的环状苄醚与各种由Na 2 S 2 O 8介导的简单羰基化合物的交叉脱氢偶联。羰基成分的范围很广，包括简单的醛以及酮。基于经济和环境因素，使用Na 2 S 2 O 8作为CDC反应的氧化剂是有吸引力的。
• Decarboxylative Alkylation of<i>β</i>-Keto Acids with Isochromans under Oxidative Conditions
  作者：Yan Chen、Shi-Kai Tian

  DOI：10.1002/cjoc.201200994

  日期：2013.1

  An unprecedented decarboxylative alkylation reaction of β‐keto acids with isochromans has been developed under oxidative conditions. A range of β‐keto acids smoothly undergo decarboxylative alkylation with isochromans in the presence of 2,2,6,6‐tetramethylpiperdine‐1‐oxoammonium hexafluorophosphate to give structurally diverse 1‐acylmethylisochromans in moderate to excellent yields with extremely high

  在氧化条件下，β-酮酸与异色团发生了前所未有的脱羧烷基化反应。在2,2,6,6-四甲基哌啶-1-氧代铵六氟磷酸酯的存在下，一系列β-酮酸能顺利地与异色团进行脱羧烷基化反应，从而以适中至优异的产率提供结构多样的1-酰基甲基异色烷，并具有极高的区域选择性。
• Manganese Dioxide–Methanesulfonic Acid Promoted Direct Dehydrogenative Alkylation of sp³ C–H Bonds Adjacent to a Heteroatom
  作者：Xigong Liu、Bin Sun、Zhiyu Xie、Xiaojun Qin、Lei Liu、Hongxiang Lou

  DOI：10.1021/jo4000674

  日期：2013.4.5

  A manganese dioxide (MnO2)-methanesulfonic acid (CH3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation. The alkylation proceeds smoothly under air atmosphere to afford the corresponding products in good to excellent yields (53-87%). The employment of the combination of MnO2 and CH3SO3H is attractive on the basis of economical and environmental issues.