3-[(4-Methylphenyl)methyl]but-3-en-1-ol | 868748-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(4-Methylphenyl)methyl]but-3-en-1-ol
• CAS: 868748-01-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: RGTMTQJNVBXSJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-[(4-Methylphenyl)methyl]but-3-en-1-ol 在 4-二甲氨基吡啶 、 2,4,6-Triisopropylthiophenol 、 C₄₂H₃₄F₁₀IrN₄⁽¹⁺⁾*F₆P^(1-) 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-((4-(tert-butyl)phenyl)sulfonyl)-3-(4-methylbenzyl)pyrrolidine
  参考文献：
  名称：

  Cyclic Amine Synthesis via Catalytic Radical‐Polar Crossover Cycloadditions

  摘要：

  The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical‐polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct β, β‐disubstituted cyclic amine and β‐monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open‐shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion.

  DOI：

  10.1002/anie.202401671
• 作为产物：
  描述：

  3-溴-3-丁烯醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 四氢呋喃 为溶剂， 生成 3-[(4-Methylphenyl)methyl]but-3-en-1-ol
  参考文献：
  名称：

  Cyclic Amine Synthesis via Catalytic Radical‐Polar Crossover Cycloadditions

  摘要：

  The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical‐polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct β, β‐disubstituted cyclic amine and β‐monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open‐shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion.

  DOI：

  10.1002/anie.202401671

文献信息

• Regioselective Synthesis of 2,6-Dimethyltetralin:  Key Precursor to 2,6-Dimethylnaphthalene
  作者：Byung Hyun Kim、Jong Gil Lee、Woon Ki Kim、Young Gyu Kim

  DOI：10.1021/op050072g

  日期：2005.11.1

  available 4-bromotoluene and 3-methyl-3-buten-1-ol, the catalytic reduction of the coupling products, and the acid-catalyzed cyclization of the alcohol intermediate. The process has an advantage over the established processes in that 2,6-DMT is obtained as the only isomer, and the isomerization and/or the complicated separation and purification steps are not required to produce pure 2,6-DMT. 2,6-DMN could

  描述了2,6-二甲基四氢萘（2,6-DMT）（2,6-二甲基萘（2,6-DMN）的关键前体）的一种新的区域选择性合成方法。合成包括以下三个步骤：市售的4-溴甲苯和3-甲基-3-丁烯-1-醇之间的Heck反应，偶联产物的催化还原以及醇中间体的酸催化环化反应。该方法相对于已建立的方法的优点在于，获得了2，6-DMT作为唯一的异构体，并且不需要异构化和/或复杂的分离和纯化步骤来生产纯的2，6-DMT。取决于环化条件，也可以将2，6-DMN作为主要产物获得。
• Novel process for preparation of 2,6-dialkyltetralin
  申请人：Kim Gyu Young

  公开号：US20060020153A1

  公开（公告）日：2006-01-26

  The present invention provides a novel process for highly selective preparation of 2,6-dialkyltetralin, a key precursor for 2,6-dimethylnaphthalene (2,6-DMN), which does not require an extra step for purifying various isomers obtained from the conventional processes for 2,6-DMN. The present invention is advantageous to improve the synthetic yield, to simplify the operation and thus to reduce the production cost, since different starting materials and different pathways are exploited and thus the additional steps are not necessary.

  本发明提供了一种新颖的工艺，用于高度选择性地制备2,6-二烷基四氢萘，这是2,6-二甲基萘（2,6-DMN）的关键前体，不需要额外的步骤来纯化从传统工艺中获得的各种异构体。本发明有利于提高合成产率，简化操作，从而降低生产成本，因为利用不同的起始材料和不同的途径，因此不需要额外的步骤。
• US7525001B2
  申请人：——

  公开号：US7525001B2

  公开（公告）日：2009-04-28
• Cyclic Amine Synthesis via Catalytic Radical‐Polar Crossover Cycloadditions
  作者：Ying Zhang、Shu‐Sheng Chen、Kai‐Dian Li、Huan‐Ming Huang

  DOI：10.1002/anie.202401671

  日期：2024.4.24

  The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical‐polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct β, β‐disubstituted cyclic amine and β‐monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open‐shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion.