2,2,3-trimethyl-1-(p-tolyl)but-3-en-1-ol

• 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: 2,2,3-trimethyl-1-(p-tolyl)but-3-en-1-ol
• 英文别名: 2,2,3-Trimethyl-1-(4-methylphenyl)but-3-en-1-ol；2,2,3-trimethyl-1-(4-methylphenyl)but-3-en-1-ol
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: DWNDSJYJKKCHDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 2,3-二甲基-1,3-丁二烯 在 甲醇 、 二苯基硅烷 、 二丁基二碘锡烷 、 dibutylstannane 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以46%的产率得到2,2,3-trimethyl-1-(p-tolyl)but-3-en-1-ol
  参考文献：
  名称：

  1,3-丁二烯与乙二醛氢化物催化的醛的无过渡金属还原偶联

  摘要：

  在这项研究中，开发了Bu 2 SnIH催化的1,3-二烯与醛的直接偶联。该反应可以适合于不使用过渡金属催化剂的偶联。许多类型的醛被用于该反应。MeOH的加入促进了催化循环。

  DOI：

  10.1021/acs.orglett.7b02671

文献信息

• Generation of Allylic Indium by Hydroindation of 1,3-Dienes and One-Pot Reaction with Carbonyl Compounds
  作者：Naoki Hayashi、Hiroyuki Honda、Makoto Yasuda、Ikuya Shibata、Akio Baba

  DOI：10.1021/ol061797n

  日期：2006.9.1

  A hydroindation of 1,3-dienes by dichloroindium hydride (HInCl2) generates allylic indiums that react with carbonyl or imine moieties in a one-pot treatment. The former reaction proceeds in a radical manner, and the latter is ionic allylation. Moreover, both reactions require no additives such as radical initiators, Lewis acids, or transition metal catalysts.

  通过二氯氢化铟（HInCl2）对1,3-二烯进行加氢精制会生成烯丙基铟，它们在一键处理中会与羰基或亚胺基反应。前者以自由基方式进行，后者是离子烯丙基化。而且，两个反应都不需要添加剂，例如自由基引发剂，路易斯酸或过渡金属催化剂。
• Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis
  作者：Xian‐Wang Zeng、Jia‐Ni Lin、Wei Shu

  DOI：10.1002/anie.202403073

  日期：2024.6.3

  Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.