1-(4-methylphenyl)-isochroman | 1445853-51-9

• 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: 1-(4-methylphenyl)-isochroman
• 英文别名: 3,4-dihydro-1-(4-methylphenyl)-1H-2-benzopyran；1-(4-methylphenyl)-3,4-dihydro-1H-isochromene
• CAS: 1445853-51-9
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: AGPIJJSTLHGQJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-碘甲苯 在 2-羟基-2-氮杂金刚烷 、 [bis(trifluoroacetoxy)iodo]benzene 、 碘 、 magnesium 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 21.0h， 生成 1-(4-methylphenyl)-isochroman
  参考文献：
  名称：

  Efficient C(sp³)–H Bond Functionalization of Isochroman by AZADOL Catalysis

  摘要：

  A novel organocatalytic C(sp(3))-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.

  DOI：

  10.1021/acs.orglett.5b00434

文献信息

• 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。
• Simple and Direct sp³ C–H Bond Arylation of Tetrahydroisoquinolines and Isochromans via 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Oxidation under Mild Conditions
  作者：Wataru Muramatsu、Kimihiro Nakano、Chao-Jun Li

  DOI：10.1021/ol401534g

  日期：2013.7.19

  The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp3 C–H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction between readily available aryl Grignard reagents and iminium (or oxonium) cations generated in situ by DDQ oxidation of tetrahydroisoquinolines (or isochromans) under

  描述了2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）介导的四氢异喹啉和异色满的sp 3 C–H键芳基化。通过容易获得的芳基格氏试剂与在温和条件下通过四氢异喹啉（或异色满）的DDQ氧化就地生成的亚胺（或氧鎓）阳离子之间的简单亲核加成反应，可以轻松合成相应的产物。
• Organocatalytic Approach for C(sp³)–H Bond Arylation, Alkylation, and Amidation of Isochromans under Facile Conditions
  作者：Wataru Muramatsu、Kimihiro Nakano

  DOI：10.1021/ol5006399

  日期：2014.4.4

  the synthesis of isochroman derivatives via direct C(sp3)–H bond arylation is described. The oxidation reaction with [bis(trifluoroacetoxy)iodo]benzene facilitates the regeneration of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in the C(sp3)–H bond arylation of isochroman. The reaction conditions can also be used for alkyl Grignard reagents and amides to afford the corresponding isochroman derivatives.

  描述了一种通过直接C（sp 3）-H键芳基化合成异色满衍生物的新催化方法。与[双（三氟乙酰氧基）碘]苯的氧化反应促进异色满的C（sp 3）-H键芳基化反应中2,3-二氯-5,6-二氰基-1,4-苯醌的再生。反应条件也可用于烷基格氏试剂和酰胺，以得到相应的异色满衍生物。
• Transition-Metal-Free Cross-Coupling of Indium Organometallics with Chromene and Isochroman Acetals Mediated by BF₃·OEt₂
  作者：José M. Gil-Negrete、José Pérez Sestelo、Luis A. Sarandeses

  DOI：10.1021/acs.orglett.6b02058

  日期：2016.9.2

  coupling of triorganoindium reagents with benzopyranyl acetals mediated by a Lewis acid has been developed. The reaction of R3In with chromene and isochroman acetals in the presence of BF3·OEt2 afforded 2-substituted chromenes and 1-substituted isochromans, respectively, in good yields. The reactions proceed with a variety of triorganoindium reagents (aryl, heteroaryl, alkynyl, alkenyl, alkyl) using

  已经开发了由路易斯酸介导的三有机铟试剂与苯并吡喃基乙缩醛的无过渡金属偶联。在BF 3 ·OEt 2的存在下，R 3 In与亚甲基苯并异铬烷醛的缩醛反应，分别以高收率得到2-取代的苯并二烯和1-取代的异苯并二氢吡喃。反应仅使用50 mol％的有机金属，通过各种三有机铟试剂（芳基，杂芳基，炔基，烯基，烷基）进行，因此证明了这些物质的效率。初步的机理研究表明在路易斯酸存在下氧碳carb离子中间体的形成。