(E)-1-(3-methoxy-3-methylbut-1-en-1-yl)-4-methylbenzene | 349668-02-6

• 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: (E)-1-(3-methoxy-3-methylbut-1-en-1-yl)-4-methylbenzene
• 英文别名: 1-[(E)-3-methoxy-3-methylbut-1-enyl]-4-methylbenzene
• CAS: 349668-02-6
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: HYEOONVAJXYGLQ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-methoxy-3-methylbut-1-en-1-yl)-4-methylbenzene 在 正丁基锂 、 四甲基乙二胺 、 potassium tert-butylate 、 重水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 以93%的产率得到1-(deuteriomethyl)-4-[(E)-3-methoxy-3-methylbut-1-enyl]benzene
  参考文献：
  名称：

  Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene

  摘要：

  The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the pi* orbital of the benzene ring and the sigma orbital of the vinylic C-H bond in the twisted styrene derivatives.

  DOI：

  10.1021/jo061092z
• 作为产物：
  描述：

  2-甲基-4-(4-甲基苯基)丁-3-炔-2-醇 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 (E)-1-(3-methoxy-3-methylbut-1-en-1-yl)-4-methylbenzene
  参考文献：
  名称：

  Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene

  摘要：

  The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the pi* orbital of the benzene ring and the sigma orbital of the vinylic C-H bond in the twisted styrene derivatives.

  DOI：

  10.1021/jo061092z

文献信息

• Copper and neocuproine catalysed synthesis of cinnamyl ether derivatives directly from secondary and tertiary cinnamyl alcohols
  作者：Zhenjiao Yang、Yongsheng Zhang、Xingxian Lv、Yang Yang、Chunhao Jiang、Xiaoyan He、Guoliang Chen、Gang Huang、Xiuhong Lu

  DOI：10.1039/d2gc01602h

  日期：——

  The skeletons of secondary and tertiary cinnamyl alcohols are found ubiquitously in natural products and commercial drugs. Due to the easy dehydration of their structures, the etherification of such compounds is often difficult. A new method for the synthesis of secondary and tertiary cinnamyl ether derivatives, employing copper sulfate pentahydrate (CuSO4·5H2O) as a catalyst and neocuproine as a ligand

  仲和叔肉桂醇的骨架普遍存在于天然产物和商业药物中。由于它们的结构容易脱水，这些化合物的醚化通常很困难。建立了以五水硫酸铜(CuSO 4 ·5H 2 O)为催化剂，新铜碱为配体的二、叔肉桂醚衍生物的合成新方法。有趣的是，这种方法能够使长烷氧基链与仲或叔肉桂醇有效连接。通过该方法，实现了含有天然产物和小分子药物的PEG修饰的肉桂醇仲醇和叔醇，为直接生成功能性肉桂醚衍生物提供了一种绿色方法。
• Iridium-Catalyzed 1,3-Rearrangement of Allylic Ethers
  作者：Fei Li、Jinbao Ren、Yifan Song、Qianjia Yuan、Deyue Yan、Wanbin Zhang

  DOI：10.1021/acs.orglett.3c03661

  日期：2023.12.8

  The 1,3-rearrangement of allylic derivatives has rarely been reported, except for allylic alcohols. Herein, we describe an iridium-catalyzed 1,3-rearrangement of readily available allylic ethers to access the difficultly prepared allylic ethers with a large steric hindrance. The developed method shows a broad substrate scope and could be used in the late-stage modification of several natural products

  除烯丙醇外，烯丙衍生物的1,3-重排很少有报道。在此，我们描述了一种铱催化的容易获得的烯丙醚的1,3-重排，以得到难以制备的具有大空间位阻的烯丙醚。所开发的方法具有广泛的底物范围，可用于多种天然产物的后期修饰。此外，在对照实验的基础上还提供了可能的反应途径。
• Vinyl hydrogen more reactive than benzyl hydrogen toward base in significantly twisted styrenes
  作者：Hajime Mori、Takafumi Matsuo、Yasunori Yoshioka、Shigeo Katsumura

  DOI：10.1016/s0040-4039(01)00308-2

  日期：2001.4

  The novel example of vinyl hydrogen more reactive than benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. The characteristic nature of the vinyl hydrogen, which is activated by sigma-pi* orbital interaction, was apparently demonstrated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene
  作者：Hajime Mori、Takafumi Matsuo、Yasunori Yoshioka、Shigeo Katsumura

  DOI：10.1021/jo061092z

  日期：2006.11.1

  The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the pi* orbital of the benzene ring and the sigma orbital of the vinylic C-H bond in the twisted styrene derivatives.