1,2-dihydro-2,2-dimethylnaphtho[2,1-b]furan | 33563-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 1,2-dihydro-2,2-dimethylnaphtho[2,1-b]furan
• 英文别名: 2,2-dimethyl-1,2-dihydronaphtho[2,1-b]furan；2,2-Dimethyl-1,2-dihydro-naphtho[2,1-b]furan；2,2-dimethyl-1H-benzo[e][1]benzofuran
• CAS: 33563-17-6
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: OZQXYQYUDZMKAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-((2-methylallyl)oxy)naphthalene 生成 1,2-dihydro-2,2-dimethylnaphtho[2,1-b]furan
  参考文献：
  名称：

  1-Alkyl-1,2,3,4-tetrahydro-2-naphthols

  摘要：

  DOI：

  10.1021/ja01186a061

文献信息

• [EN] INTRODUCTION OF ALKYL SUBSTITUENTS TO AROMATIC COMPOUNDS<br/>[FR] INTRODUCTION DE SUBSTITUANTS ALKYLE DANS DES COMPOSÉS AROMATIQUES
  申请人：B G NEGEV TECH AND APPLICATIONS LTD AT BEN-GURION UNIV

  公开号：WO2016132355A1

  公开（公告）日：2016-08-25

  Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.

  披露了一种新颖的选择性合成路线，用于在芳香化合物上引入初级烷基团。该合成路线基于在芳香取代反应中生成的硫正离子物种，这些硫正离子物种是从醛和硫醇原位生成的，从而得到可以与三乙基硅烷还原的苯甲基硫醚。
• Convenient synthesis of novel 2,2-dialkyl-1,2-dihydronaphtho[2,1-b]furans
  作者：Doug Vaughan、Amitabh Jha

  DOI：10.1016/j.tetlet.2009.07.087

  日期：2009.10

  2,2-dialkylacetaldehydes with electron-rich 2-naphthols in presence of p-TSA under closed-vessel solvent-free microwave irradiation conditions resulted in formation of corresponding dihydronaphtho[2,1-b]furans in good to excellent yields. In several cases, small amounts of 14-alkyl-14H-dibenzo[a,j]xanthenes were also formed.

  2，2-二烷基乙醛与p -TSA存在下的富电子2-萘在密闭容器无溶剂微波辐射条件下反应，可形成相应的二氢萘[2，1- b ]呋喃，收率高至优异。在几种情况下，还形成了少量的14-烷基-14 H-二苯并[ a，j ]蒽。
• Introduction of alkyl substituents to aromatic compounds
  申请人：B. G. NEGEV TECHNOLOGIES AND APPLICATIONS LTD., AT BEN-GURION UNIVERSITY

  公开号：US10351492B2

  公开（公告）日：2019-07-16

  Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.

  本发明公开了在芳香族化合物上引入伯烷基的新型选择性合成路线。该合成路线基于由醛和硫醇原位生成的硫离子物种的亲电芳香取代，从而得到可被三乙基硅烷还原的苄基硫醚。
• High-Yielding Palladium-Catalyzed Intramolecular Alkane Arylation:  Reaction Development and Mechanistic Studies
  作者：Marc Lafrance、Serge I. Gorelsky、Keith Fagnou

  DOI：10.1021/ja076588s

  日期：2007.11.28

  Palladium-catalyzed alkane arylation reactions with aryl halides are described for the preparation of 2,2-dialkyl-dihydrobenzofuran substrates. These reactions occur in excellent yield and very high selectivity for the formation of one sole product arising from a reaction at nearby methyl groups. Mechanistic and computational studies point to the involvement of a concerted, inner-sphere palladation-deprotonation pathway that is enabled by the presence of three-center agostic interactions at the transition state. This mechanism accurately predicts the experimentally observed kinetic isotope effect as well as the site selectivity and should be useful in the design of new reactions and catalysts.
• Reductive Alkylation of Arenes by a Thiol-Based Multicomponent Reaction
  作者：Regev Parnes、Doron Pappo

  DOI：10.1021/acs.orglett.5b01142

  日期：2015.6.19

  A simple and highly chemo- and regioselective method for introducing primary alkyl substituents into aromatic compounds was developed. The method is based on an electrophilic aromatic substitution of an aldehyde, promoted by a thiol, to afford 1-(alkylthio)alkylarenes, which can either be reduced in situ with triethylsilane or reacted further. This multicomponent reaction enables the direct introduction of both aromatic and linear and branched aliphatic alkyl groups into arenes. The above one-pot protocol may be performed in air and in the presence of water and is compatible with various functional groups.