1-[(E)-3,3-dimethoxyprop-1-enyl]-2-methoxybenzene | 1171019-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(E)-3,3-dimethoxyprop-1-enyl]-2-methoxybenzene
• CAS: 1171019-85-4
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: CJFBAIORUYSJHT-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(E)-3,3-dimethoxyprop-1-enyl]-2-methoxybenzene 在 盐酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 以0.046 g的产率得到2-甲氧基肉桂醛
  参考文献：
  名称：

  2,2-二甲氧基乙基PT砜的Julia-Kocienski反应接着酸水解一锅法制备（E）-α，β-不饱和醛

  摘要：

  （E）-α，β-不饱和醛是通过2，2-二甲氧基乙基1-苯基-1 H-四唑-5-基（PT）砜3的Julia-Kocienski反应与各种醛合成的，然后进行酸水解。该反应可以在一个锅中进行，并且在短时间内以高收率获得了各种（E）-α，β-不饱和醛。

  DOI：

  10.1021/acs.joc.1c00479
• 作为产物：
  描述：

  丙烯醛二甲缩醛 、 2-碘苯甲醚 在 potassium chloride 、 四丁基醋酸铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-[(E)-3,3-dimethoxyprop-1-enyl]-2-methoxybenzene
  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

• Nickel(II)-catalyzed asymmetric alkylation of acyclic oxocarbenium ions with carboxylic acid derivatives
  作者：Pengbo Ye、Xuan Liu、Gang Wang、Lei Liu

  DOI：10.1016/j.cclet.2020.08.034

  日期：2021.3

  A nickel(II)-catalyzed asymmetric alkylation of acyclic oxocarbenium ions generated in situ from corresponding acetals with carboxylic acid derivatives to prepare β-alkoxyl carbonyl moieties with diverse α-substituents has been disclosed. The method exhibited broad scope of acetals and carboxylic acid derivatives with excellent enantioselectivity and good functional group compatibility, and can be

  已经公开了由镍（II）催化的从相应的缩醛与羧酸衍生物就地产生的无环氧碳鎓离子的不对称烷基化，以制备具有各种α-取代基的β-烷氧基羰基部分。该方法显示出范围广泛的乙缩醛和羧酸衍生物，具有优异的对映选择性和良好的官能团相容性，并且可以以克为单位进行操作而没有明显的效率损失。
• The use of 1,2-O-isopropylidene-α-d-xylofuranose as a chiral auxiliary in asymmetric cyclopropanation reactions
  作者：José M. Vega-Pérez、Ignacio Periñán、Fernando Iglesias-Guerra

  DOI：10.1016/j.tetasy.2009.02.062

  日期：2009.5

  1,2-O-isopropylidene-d-xylofuranose, as a chiral auxiliary, is described. The Simmons–Smith cyclopropanation reaction of the corresponding alkenylidene derivatives with CH2I2/ZnEt2, in different reaction conditions, took place with high stereoselectivity. The diastereomeric excess in each case depended on the solvent and the temperature used in the reaction. The absolute configuration of the new stereogenic

  描述了衍生自作为手性助剂的1,2 - O-异亚丙基-d-木呋喃糖的环丙基亚甲基缩醛的立体选择性合成。在不同的反应条件下，相应的链烯基衍生物与CH 2 I 2 / ZnEt 2的Simmons-Smith环丙烷化反应具有很高的立体选择性。在每种情况下，非对映异构体过量取决于反应中所用的溶剂和温度。通过手性助剂的环丙烷部分的酸水解确定了形成的新的立体异构中心的绝对构型，该手性助剂也被回收了。
• Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate <i>Staphylococcus aureus</i> Infections in Vivo
  作者：Shuaishuai Ni、Hanwen Wei、Baoli Li、Feifei Chen、Yifu Liu、Wenhua Chen、Yixiang Xu、Xiaoxia Qiu、Xiaokang Li、Yanli Lu、Wenwen Liu、Linhao Hu、Dazheng Lin、Manjiong Wang、Xinyu Zheng、Fei Mao、Jin Zhu、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.7b00949

  日期：2017.10.12

  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.
• One-Pot Preparation of (<i>E</i>)-α,β-Unsaturated Aldehydes by a Julia–Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis
  作者：Kaori Ando、Haruka Watanabe、Xiaoxian Zhu

  DOI：10.1021/acs.joc.1c00479

  日期：2021.5.7

  (E)-α,β-Unsaturated aldehydes were synthesized by the Julia–Kocienski reaction of 2,2-dimethoxyethyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfone 3 with various aldehydes, followed by acid hydrolysis. The reaction could be carried out in one pot, and various (E)-α,β-unsaturated aldehydes were obtained in a short time and with high yields.

  （E）-α，β-不饱和醛是通过2，2-二甲氧基乙基1-苯基-1 H-四唑-5-基（PT）砜3的Julia-Kocienski反应与各种醛合成的，然后进行酸水解。该反应可以在一个锅中进行，并且在短时间内以高收率获得了各种（E）-α，β-不饱和醛。