2-methyl-4-phenylbut-3-en-2-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 2-methyl-4-phenylbut-3-en-2-ol
• 英文别名: 3-Methyl-1-phenyl-buten-3-ol
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: AHTMRLFEKXDXJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-methyl-4-phenylbut-3-en-2-ol 在 tetrahydropyrrolo[2,1-c][1,2,4]triazole carbene 、 二苯基硅烷 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 四氢呋喃 为溶剂， 反应 0.5h， 以99%的产率得到2-甲基-4-苯基-2-丁醇
  参考文献：
  名称：

  苯乙烯和炔丙醇与二氢硅烷的N杂环碳催化氢化硅烷化

  摘要：

  减少烯烃的眼泪：在硅上添加结构多样的N杂环卡宾（NHC），可通过有机催化的甲硅烷基化/直接氢化物转移串联反应还原炔丙醇和苯乙烯醇（参见方案）。切换到高价硅可以实现催化转换。这为NHC-主族元素配合物提供了新的合成应用。

  DOI：

  10.1002/chem.201101822
• 作为产物：
  描述：

  2-甲基-4-苯基-3-丁炔-2-醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以50%的产率得到2-methyl-4-phenylbut-3-en-2-ol
  参考文献：
  名称：

  Stereoselective Synthesis of 1,3-Dienes from Propargylic Alcohols by LiAlH₄/AlCl₃

  摘要：

  Herein we report that LiAlH4/AlCl3 is a very efficient reagent for the reductive dehydration of aryl propargylic alcohols in tetrahydrofuran solvent at reflux to give 1,3-dienes with good yields and high E selection. The reaction conditions are mild and easy to operate, and a variety of aryl functional groups, such as bromo, fluoro, butyl, and methoxyl groups, are tolerated. With our protocol, useful (E,E)-1,3-dienes can be synthesized. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.711881

文献信息

• Calcium-Catalyzed Friedel-Crafts Alkylation at Room Temperature
  作者：Meike Niggemann、Matthias J. Meel

  DOI：10.1002/anie.200907227

  日期：2010.5.10

  A novel calcium catalyst was found to efficiently functionalize electron‐rich arenes with secondary and tertiary benzylic, propargylic, and allylic alcohols under very mild reaction conditions. The new catalyst system significantly enlarges the scope of the reaction, which was previously limited except for the few examples with secondary benzylic alcohols.

  发现了一种新型的钙催化剂，可以在非常温和的反应条件下，用仲和叔苄醇，炔丙基和烯丙基醇有效地官能化富电子芳烃。新的催化剂体系极大地扩大了反应范围，该反应范围以前受到限制，除了少数具有仲苄醇的实例。
• Gold-Catalyzed 1,4-Carbooxygenation of 3-En-1-ynamides with Allylic and Propargylic Alcohols<i>via</i>Non-Claisen Pathways
  作者：Sovan Sundar Giri、Li-Hsuan Lin、Prakash Daulat Jadhav、Rai-Shung Liu

  DOI：10.1002/adsc.201601092

  日期：2017.2.20

  Gold‐catalyzed 1,4‐carbooxygenations of 3‐en‐1‐ynamides with allylic alcohols and propargylic alcohols yield α,β‐unsaturated amides through non‐Claisen pathways; the mechanisms involve ionization of the initial gold enol ethers to form C‐bound gold dienolates that capture allylic or propargylic cations to yield the observed products. Our 18O‐labeling experiments exclude a direct gold‐catalyzed allylation

  金与烯丙基醇和炔丙醇催化3-烯-1-炔酰胺的1,4-碳氧合反应通过非克莱森途径产生α，β-不饱和酰胺。该机制涉及将最初的金烯醇醚电离形成C键的金二烯酸酯，后者捕获烯丙基或炔丙基阳离子以生成观察到的产物。我们的18个O标记实验不包括在这些3 en-1酰胺上直接进行金催化的烯丙基化或炔丙基化。
• Efficient hydroarylation of terminal alkynes with sodium tetraphenylborate performed in water under mild conditions
  作者：P. Kocięcka、A.M. Trzeciak

  DOI：10.1016/j.apcata.2019.117243

  日期：2020.1

  The hydroarylation of terminal alkynes with sodium tetraphenylborate was performed in high yield within 3 h at room temperature in water, using palladium(II) complexes with imidazole ligands as catalysts. Under these conditions, differently substituted phenylacetylene substrates were converted to arylalkenes and aryl-substituted dienes. High conversion and excellent selectivity were achieved in the

  使用具有咪唑配体的钯（II）配合物在室温下于室温下于水中在3小时内以高收率将末端炔烃与四苯硼酸钠进行加氢芳基化反应。在这些条件下，将不同取代的苯乙炔底物转化为芳基烯烃和芳基取代的二烯。在炔醇与四苯硼酸钠的加氢芳基化反应中实现了高转化率和出色的选择性。在这些反应中仅形成一种产物，具有OH基的芳基烯烃，其产率取决于所用炔醇的种类。根据反应混合物中鉴定出的钯种类和H / D交换研究，提出了合理的加氢芳基化反应机理。证明了水作为氢化物来源的贡献。
• Direct Catalytic Azidation of Allylic Alcohols
  作者：Magnus Rueping、Carlos Vila、Uxue Uria

  DOI：10.1021/ol203310h

  日期：2012.2.3

  catalytic azidation of primary, secondary, and tertiary allylic alcohols has been developed. This new azidation reaction affords the corresponding allylic azides in high to excellent yields and regioselectivities. The reaction provides straightforward access to allylic azides that are valuable intermediates in organic synthesis, including the preparation of primary amines or 1,2,3-triazole derivatives

  已经开发了伯，仲和叔烯丙基醇的直接催化叠氮化。该新的叠氮化反应以高至优异的产率和区域选择性提供了相应的烯丙基叠氮化物。该反应提供了直接获得烯丙基叠氮化物的途径，该烯丙基叠氮化物是有机合成中有价值的中间体，包括伯胺或1,2,3-三唑衍生物的制备。
• Design and synthesis of the basic Cu-doped zeolite X catalyst with high activity in oxidative coupling reactions
  作者：Shengchun Chen、Zhen Shao、Zhongxue Fang、Qun Chen、Ting Tang、Wenqian Fu、Lei Zhang、Tiandi Tang

  DOI：10.1016/j.jcat.2016.01.030

  日期：2016.6

  shows extraordinary high activity in the decarboxylative coupling of cinnamic acids with alcohols. In addition, the Cu-X catalyst presents excellent performance in the oxidative coupling of alkenes with aldehydes. The strong interaction between Cu+ and the zeolite framework benefits the transformation of Cu2+ and Cu+ in the redox process, enhancing the reaction activity. More importantly, the Lewis basic

  肉桂酸与醇的脱羧偶联以及烯烃与醛的氧化偶联是典型的有机反应。考虑到反应的特点和机理，合成了具有路易斯碱性位点的掺铜沸石X催化剂（Cu-X）​​，并用于两个反应。与Cu，Cu 2 O和CuBr 2催化剂（4-21％）相比，Cu-X催化剂（99％）在肉桂酸与醇类的脱羧偶联中显示出非凡的高活性。另外，Cu-X催化剂在烯烃与醛的氧化偶联中表现出优异的性能。Cu +与沸石骨架之间的强相互作用有利于Cu 2+和Cu +的转变在氧化还原过程中，提高了反应活性。更重要的是，Cu-X催化剂上的Lewis碱性位点可能有利于肉桂酸的吸附，导致C C键中的电子富集密度，因此大大提高了反应活性。