6-(4-methylbenzyl)benzo[d][1,3]dioxol-5-ol | 1601466-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-(4-methylbenzyl)benzo[d][1,3]dioxol-5-ol
• 英文别名: 6-[(4-Methylphenyl)methyl]-1,3-benzodioxol-5-ol
• CAS: 1601466-98-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: HMTUKTMSYSTVOV-UHFFFAOYSA-N

物化性质

• 沸点：
  399.4±31.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-methylbenzyl)benzo[d][1,3]dioxol-5-ol 在 间苯二甲酸 、 C₁₀H₂₄N₂*C₂HF₆NO₄S₂ 、 silver(l) oxide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 27.5h， 生成
  参考文献：
  名称：

  手性伯胺催化不对称逆克莱森反应高度立体选择性构建β,β-二芳基-α-支化酮

  摘要：

  已经通过手性伯胺催化开发了β-二酮与邻醌甲基化物的高度非对映和对映选择性逆克莱森反应。该反应允许以中等至良好的收率有效合成手性 β,β-二芳基-α-支链酮，并具有优异的立体选择性。该反应通过苄基 C-C 键形成、C-C 键断裂和立体定向烯胺质子化的串联顺序发生。该策略使用邻醌甲基化物作为二芳基前体，具有广泛的底物范围、温和的条件和高度的立体控制。

  DOI：

  10.1021/acs.orglett.2c00435
• 作为产物：
  描述：

  (6-hydroxybenzo[d][1,3]dioxol-5-yl)(p-tolyl)methanone 在 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以79%的产率得到6-(4-methylbenzyl)benzo[d][1,3]dioxol-5-ol
  参考文献：
  名称：

  通过由2-烷基取代的苯酚生成的邻醌醌简化的2,3-二氢苯并呋喃合成

  摘要：

  AbstractA facile method for the stereoselective synthesis of trans‐2,3‐dihydrobenzofurans from ortho‐quinone methides in situ generated from readily available 2‐alkyl‐substituted phenols using silver oxide‐mediated oxidation has been developed. Additionally, the 2,3‐dihydrobenzofurans can be further transformed into the aromatized 2,3‐disubstituted benzofurans in the presence of DDQ.magnified image

  DOI：

  10.1002/adsc.201300830

文献信息

• C–H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4<i>H</i>-chromenes
  作者：Bo Wu、Xiang Gao、Zhong Yan、Mu-Wang Chen、Yong-Gui Zhou

  DOI：10.1021/acs.orglett.5b03148

  日期：2015.12.18

  A streamlined method for the enantioselective synthesis of 2-amino-4H-chromenes from readily available 2-alkyl-substituted phenols and active methylene compounds bearing a cyano group with up to 97% ee is presented. This reaction is a cascade procedure including manganese dioxide mediated C–H oxidation for the generation of o-quinone methides and bifunctional squaramide-catalyzed Michael addition/cyclization

  提出了一种简化的方法，用于从容易获得的2-烷基取代的苯酚和带有氰基的具有高达97％ee的活性亚甲基化合物对映选择性地合成2-氨基-4 H-色烯。该反应是一个级联过程，包括二氧化锰介导的C–H氧化，用于生成邻醌甲基化物和双功能方酰胺催化的迈克尔加成/环化反应。
• Visible-light-induced [4 + 2] cycloaddition of pentafulvenes by organic photoredox catalysis
  作者：Kenta Tanaka、Yosuke Asada、Yujiro Hoshino、Kiyoshi Honda

  DOI：10.1039/d0ob01151g

  日期：——

  We have developed thioxanthylium photoredox catalyzed [4 + 2] cycloaddition of pentafulvenes at room temperature under green light irradiation, which affords tetrahydrocyclopenta[b]chromenes with high regioselectivities. The present reaction provides a sustainable approach to carry out the cycloaddition of pentafulvenes without the use of transition metal catalysts or high-temperature conditions. This

  我们开发了在室温下绿光照射下硫代黄鎓光氧化还原催化的五富烯的 [4 + 2] 环加成反应，得到具有高区域选择性的四氢环戊二烯[ b ]色烯。本反应提供了一种可持续的方法来进行五富烯的环加成，而无需使用过渡金属催化剂或高温条件。该程序可以温和而直接地获得 1,3a,9,9a-四氢环戊二烯[ b ]色烯。反应的量子产率（Φ =0.15）表明反应主要通过光催化途径进行。
• Enantioselective one-pot synthesis of 2-amino-4<i>H</i>-chromenes via C−H oxidation and Michael addition/ring closure sequences
  作者：Kyeong Seop Kim、Dae Young Kim

  DOI：10.1080/00397911.2021.2024572

  日期：2022.1.17

  Abstract The chiral 2-amino-4H-chromene derivatives were obtained from 2-alkyl-substituted phenol derivatives in moderate to high yields with excellent enantioselectivities through one-pot cascade via C–H oxidation/Michael addition/ring closure sequences using a binaphthyl-modified organocatalyst with low catalyst loading (1.25 mol%).

  摘要 手性 2-氨基-4 H-色烯衍生物由 2-烷基取代的苯酚衍生物通过一锅级联通过 C-H 氧化/迈克尔加成/使用联萘的闭环序列以中等至高产率获得，具有优异的对映选择性。具有低催化剂负载量（1.25 mol％）的改性有机催化剂。
• Direct Sulfide-Catalyzed Diastereoselective [4+1] Annulations of <i>ortho</i>-Quinone Methides and Bromides
  作者：Yan-Qing Liu、Qing-Zhu Li、Hong-Ping Zhu、Xin Feng、Cheng Peng、Wei Huang、Jun-Long Li、Bo Han

  DOI：10.1021/acs.joc.8b02189

  日期：2018.10.19

  Direct sulfide organocatalysis is an emerging topic in research on synthetic chemistry. Here, an unprecedented sulfide-catalyzed diastereoselective [4+1] annulation of (in situ generated) ortho-quinone methides and bromides is reported. Notably, the robustness of such sulfide organocatalysis was demonstrated by performing the catalytic reaction under oxidative conditions without significantly affecting the reaction outcome. Various dihydrobenzofurans with diverse substituents were obtained with high isolated yields of up to 98% and remarkable diastereoselectivity (>19:1 dr in general).
• INTRODUCTION OF ALKYL SUBSTITUENTS TO AROMATIC COMPOUNDS
  申请人：B.G. NEGEV TECHNOLOGIES AND APPLICATIONS LTD., AT BEN-GURION UNIVERSITY

  公开号：US20180065904A1

  公开（公告）日：2018-03-08

  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.