(E)-3-(2-methylphenyl)-2-propenol | 501922-06-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-3-(2-methylphenyl)-2-propenol
• 英文别名: (E)-3-(o-tolyl)prop-2-en-1-ol；(E)-3-(2-methylphenyl)prop-2-en-1-ol；2-Propen-1-ol, 3-(2-methylphenyl)-, (2E)-
• CAS: 501922-06-1
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: LFTULPAVNUDILJ-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-methylphenyl)-2-propenol 在 4-phenylphenyl-diphenylmethylium tetrafluoroborate 、 三溴化磷 、 potassium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 茚
  参考文献：
  名称：

  Carbocation catalysed ring closing aldehyde–olefin metathesis

  摘要：

  在温和的反应条件和较低的催化剂负载下，4-苯基二苯基甲基四氟硼酸盐催化了一种罕见的高产率烯醛分子内醛-烯烃复分解反应。

  DOI：

  10.1039/c8cc06734a
• 作为产物：
  描述：

  2-碘代甲苯 在 盐酸 、 sodium tetrahydroborate 、 potassium chloride 、 四丁基醋酸铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (E)-3-(2-methylphenyl)-2-propenol
  参考文献：
  名称：

  Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate Staphylococcus aureus Infections in Vivo

  摘要：

  Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.

  DOI：

  10.1021/acs.jmedchem.7b00949

文献信息

• Ketenimines from Isocyanides and Allyl Carbonates: Palladium-Catalyzed Synthesis of β,γ-Unsaturated Amides and Tetrazoles
  作者：Guanyinsheng Qiu、Mathias Mamboury、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.201609034

  日期：2016.12.5

  allyl ethyl carbonates with isocyanides in the presence of a catalytic amount of Pd(OAc)2 provided ketenimines through β‐hydride elimination of the allyl imidoylpalladium intermediates. The insertion of the isocyanide into the π‐allyl Pd complex proceeded via an unusual η1‐allyl Pd species. The resulting ketenimines were hydrolyzed to β,γ‐unsaturated carboxamides during purification by flash column chromatography

  在催化量的Pd（OAc）2存在下，碳酸烯丙乙酯与异氰酸酯的反应通过烯丙基酰亚胺基钯中间体的β-氢化物消除，提供了烯酮胺。胩的插入π烯丙基钯配合物经由一个不寻常的η进行1 -烯丙基钯物种。在硅胶上通过快速柱色谱纯化时，将得到的酮亚胺水解成β，γ-不饱和羧酰​​胺，或与酸或三甲基叠氮化硅通过[3 + 2]环加成反应原位转化为1,5-二取代四唑。
• Kinetic Resolution of Acyclic Secondary Allylic Silyl Ethers Catalyzed by Chiral Ketones
  作者：Dan Yang、Guan-Sheng Jiao、Yiu-Chung Yip、Tsz-Hin Lai、Man-Kin Wong

  DOI：10.1021/jo010068c

  日期：2001.6.1

  Kinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl(3), tert-butyl, or CF(3) group at the alpha-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions

  研究了由手性酮（R）-1和（R）-2和Oxone原位生成的手性二恶英酮对无环仲烯丙基甲硅烷基醚的动力学拆分。已经开发出一种有效的催化方法来动力学拆分那些在α位置具有CCl（3），叔丁基或CF（3）基团的底物。特别地，对于酮（R）-2催化的外消旋α-三氯甲基烯丙基甲硅烷基醚7和9-15的动力学拆分，观察到高选择性（S高达100）。回收的底物和所得的环氧化物均以高对映体过量获得。根据手性二恶英和外消旋底物之间的空间和静电相互作用，
• Oxoammonium‐Mediated Allylsilane–Ether Coupling Reaction
  作者：Federica Carlet、Greta Bertarini、Gianluigi Broggini、Alexandre Pradal、Giovanni Poli

  DOI：10.1002/ejoc.202100026

  日期：2021.4.22

  An oxoammonium‐mediated α‐C(sp3) allylation of allyl‐ and benzyl ethers using allylsilanes as nucleophilic partners is disclosed. This new C−C bond forming C−H activation process allows to obtain the corresponding coupled products in moderate to good yields.

  公开了使用烯丙基硅烷作为亲核伙伴的烯丙基和苄基醚的氧铵介导的α-C（sp 3）烯丙基化反应。这种新的形成C-H键的C-C键可允许以中等到良好的产率获得相应的偶联产物。
• P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
  作者：Wenrui Xiong、Guangqing Xu、Xinhong Yu、Wenjun Tang

  DOI：10.1021/acs.organomet.9b00194

  日期：2019.10.28

  Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

  描述了使用P-手性单磷配体在烯丙基溴和烷基格氏试剂之间的不对称铜催化的烯丙基烷基化。在低至0.5mol％的铜负载下，形成具有良好支化/线性选择性和优异对映选择性的一系列带有叔碳或季碳中心的末端烯烃。
• Palladium-Catalyzed Regioselective Aerobic Allylic C−H Oxygenation: Direct Synthesis of <i>α,β</i> -Unsaturated Aldehydes and Allylic Alcohols
  作者：Chunsheng Li、Huoji Chen、Jianxiao Li、Meng Li、Jianhua Liao、Wanqing Wu、Huanfeng Jiang

  DOI：10.1002/adsc.201701324

  日期：2018.4.17

  A protocol for the synthesis of α,β‐unsaturated aldehydes and allylic alcohols from simple allylic hydrocarbons with water via palladium‐catalyzed functionalization of allylic C−H bonds was described. Molecular oxygen is utilized as the sole oxidant in this oxygenation of terminal alkenes. This protocol features good functional group compatibility, broad substrate scope, and high atom‐ and step‐economy

  描述了通过钯催化的烯丙基CH键的官能化，由简单的烯丙基烃与水合成α，β-不饱和醛和烯丙基醇的方案。在末端烯烃的这种氧化中，分子氧被用作唯一的氧化剂。该协议具有良好的官能团兼容性，广泛的底物范围以及高原子经济性和阶梯经济性。而且，该方法在合成布洛芬中的应用可以突出该方法的合成效用，布洛芬是一种非常有效的止痛药。