3,4-dihydro-1-(2-methylphenyl)-1H-2-benzopyran | 119367-98-5

• 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: 3,4-dihydro-1-(2-methylphenyl)-1H-2-benzopyran
• 英文别名: 1-(2-methylphenyl)-3,4-dihydro-1H-isochromene
• CAS: 119367-98-5
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: KQIKSZGJGMUWRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-(2-Methoxyethyl)benzaldehyde 在 溴 、 sodium hydride 、 对甲苯磺酸 、 magnesium 作用下， 以 乙醇 、 苯 为溶剂， 反应 13.0h， 生成 3,4-dihydro-1-(2-methylphenyl)-1H-2-benzopyran
  参考文献：
  名称：

  Intramolecular generation of oxonium ylides from functionalized arylcarbenes

  摘要：

  DOI：

  10.1021/ja00186a048

文献信息

• Direct Arylation of Benzyl Ethers with Organozinc Reagents
  作者：Zhihua Peng、Yilei Wang、Zhi Yu、Dezhi Zhao、Linhua Song、Cuiyu Jiang

  DOI：10.1021/acs.joc.8b00776

  日期：2018.8.3

  bond arylation of benzyl ethers with Knochel-type arylzinc reagents has been developed. This transition-metal-catalyst-free reaction proceeds well under mild conditions in a simple and effective manner and enables the synthesis of a wide range of potentially biologically active benzyl ethers by using highly functionalized organozinc reagents as a carbon nucleophile.

  已开发出一种新型的C（sp 3）–H苄基醚与Knochel型芳基锌试剂的芳基化反应。这种无过渡金属-催化剂的反应在温和条件下以简单有效的方式进行得很好，并且可以通过使用高度官能化的有机锌试剂作为碳亲核试剂来合成各种潜在的具有生物活性的苄基醚。
• 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。
• Efficient C(sp³)–H Bond Functionalization of Isochroman by AZADOL Catalysis
  作者：Wataru Muramatsu、Kimihiro Nakano

  DOI：10.1021/acs.orglett.5b00434

  日期：2015.3.20

  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.