1-(m-tolyl)prop-2-en-1-ol | 58824-47-8

• 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: 1-(m-tolyl)prop-2-en-1-ol
• 英文别名: 1-m-Tolyl-allylalkohol；α-m-Tolyl-allylalkohol；1-(3-Methylphenyl)prop-2-en-1-ol
• CAS: 58824-47-8
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: FQEWBVBXTJXRGM-UHFFFAOYSA-N

物化性质

• 沸点：
  242.5±9.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-(m-tolyl)prop-2-en-1-ol 在 氢溴酸 、 三溴化锑 、 铜 、 锌 作用下， 以 乙醚 为溶剂， 生成 1-环丙基-3-甲基苯
  参考文献：
  名称：

  Oxidative cleavage of cyclopropanes. IV. Kinetics of the cleavage of arylcyclopropanes by mercuric acetate

  摘要：

  DOI：

  10.1021/ja01008a036
• 作为产物：
  描述：

  1-(间甲基苯基)-2-丙炔-1-醇 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以90%的产率得到1-(m-tolyl)prop-2-en-1-ol
  参考文献：
  名称：

  Synthesis and biological activities of [E]-5-(2-acylvinyl)uracils

  摘要：

  The synthesis of a number of 5-substituted uracils, eg [E]-5-(2-acylvinyl)uracils 8a-8g is described. These compounds were found to have cytotoxic activities against CCRF-CEM human lymphoblastoid cells, HT-29 colon carcinoma cells and L1210/0 mouse leukemia cells. These compounds were also found to inhibit thymidylate synthase.

  DOI：

  10.1016/0223-5234(93)90015-7

文献信息

• Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates
  作者：Min Han、Min Yang、Rui Wu、Yang Li、Tao Jia、Yuanji Gao、Hai-Liang Ni、Ping Hu、Bi-Qin Wang、Peng Cao

  DOI：10.1021/jacs.0c01766

  日期：2020.8.5

  The Iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azide are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. The products are readily transformed into chiral N-containing

  介绍了铱催化的叠氮化乙烯基和烯丙基亲电试剂的对映选择性偶联反应，并提供了获得 β-手性羰基衍生物的途径。乙烯基叠氮化物用作乙酰胺烯醇化物或乙腈碳负离子替代物，导致 γ,δ-不饱和 β-取代酰胺以及具有优异对映体过量的腈。这些产品很容易转化为手性含氮积木和药物。提出了一种机制来合理化这种偶联反应的化学选择性。
• General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand
  作者：Elis Erbing、Ana Vázquez-Romero、Antonio Bermejo Gómez、Ana E. Platero-Prats、Fabian Carson、Xiaodong Zou、Päivi Tolstoy、Belén Martín-Matute

  DOI：10.1002/chem.201603825

  日期：2016.10.24

  Remarkably simple IrIII catalysts enable the isomerization of primary and sec‐allylic alcohols under very mild reaction conditions. X‐ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.

  非常简单的Ir III催化剂可在非常温和的反应条件下实现伯醇和仲烯丙基醇的异构化。X射线吸收光谱（XAS）和质谱（MS）研究表明，通式为[Cp * Ir III ]的催化剂需要卤化物配体才能发挥催化活性，但不需要添加剂或其他配体。
• Olefin Oxyamination with Unfunctionalized <i>N</i> ‐Alkylanilines
  作者：Shuang Gao、Meike Niggemann

  DOI：10.1002/adsc.201801407

  日期：2019.4

  N‐Alkylanilines have rarely been used in oxyamination reactions, due to the normally necessary pre‐functionalization of the N‐atom. Also, the formation of aminium radical cations (ARCs) of anilines bearing alkyl substituents is plagued by the ARC's tendency to instantaneously convert to α‐amino radicals or iminium ions. We present a readily available reagent combination that addresses both challenges

  由于通常需要对N原子进行预官能化，因此N烷基苯胺很少用于氧化胺化反应。同样，带有烷基取代基的苯胺的铝自由基阳离子（ARC）的形成也受到ARC立即转化为α-氨基自由基或亚胺离子的趋势的困扰。我们提出了一种既可解决上述两个难题的现成试剂组合，又可通过ARC将N-烷基苯胺进行氧化胺化，作为关键的反应中间体和出色的非对映选择性。
• Highly diastereo- and enantio-selective epoxidation of secondary allylic alcohols catalyzed by styrene monooxygenase
  作者：Hui Lin、Yan Liu、Zhong-Liu Wu

  DOI：10.1039/c0cc04360e

  日期：——

  Enantiomerically enriched glycidol derivatives with contiguous stereogenic centers were obtained in a highly diastereo- and enantio-selective epoxidation catalyzed with the styrene monooxygenase StyAB2.

  在以苯乙烯单加氧酶StyAB2作为催化剂的高度立体选择性和对映选择性环氧化反应中，获得了具有相邻立体中心的高对映体富集的缩水甘油衍生物。
• Palladium-catalyzed regioselective synthesis of B(4,5)- or B(4)-substituted <i>o</i>-carboranes containing α,β-unsaturated carbonyls
  作者：Chuyi Zhang、Qian Wang、Song Tian、Jianwei Zhang、Jiaoyi Li、Ling Zhou、Jian Lu

  DOI：10.1039/d0ob00698j

  日期：——

  With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)- or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The –COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.

  已经报道了借助于羧酸引导基团，Pd催化的含有α，β-不饱和羰基的B（4，5）-或B（4）-取代的邻-碳硼烷的区域选择性合成。在反应过程中除去的–COOH负责控制区域选择性。所需产物可以以中等至良好的产率获得。