4, 5-dimethyl-2-(prop-1-en-2-yl)phenol | 1415385-81-7

• 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: 4, 5-dimethyl-2-(prop-1-en-2-yl)phenol
• 英文别名: 4,5-Dimethyl-2-(prop-1-en-2-yl)phenol；4,5-dimethyl-2-prop-1-en-2-ylphenol
• CAS: 1415385-81-7
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: KRFXOCVTWAQNAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  1
• 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：

  4, 5-dimethyl-2-(prop-1-en-2-yl)phenol 在 N-氯代丁二酰亚胺 、 水 、 potassium carbonate 、 potassium hydrogencarbonate 作用下， 以 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 6.67h， 生成 tert-butyl 4-(4-{5-[4,5-dimethyl-2-(prop-2-yn-1-yloxy)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  PIPERIDINE PYRAZOLES AS FUNGICIDES

  摘要：

  本发明涉及杂环基哌啶和哌嗪衍生物，以及其农药活性盐、其用途，以及用于控制植物内和/或外的植物病原真菌的方法和组合物，用于生产这种组合物的方法，以及处理过的种子，以及在农业、园艺和林业中控制植物病原有害植物的使用，以及在动物健康、材料保护以及家庭和卫生领域中的使用。本发明还涉及一种生产杂环基哌啶和哌嗪衍生物的方法。

  公开号：

  US20140228404A1
• 作为产物：
  描述：

  4,6,7-trimethyl-2H-chromen-2-one 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 以64%的产率得到6-甲基百里酚
  参考文献：
  名称：

  Ethylene glycol as hydrogen donor for the syntheses of thymol analogues via hydrolysis of 4-methylcoumarins

  摘要：

  Treatment of 4-methylcoumarins with potassium hydroxide in ethylene glycol resulted in the formation of the 'normal' 2-isopropenylphenols and/or the 'abnormal' 2-isopropylphenols depending on the nature of the substrates. The solvent ethylene glycol was believed to be the hydrogen donor for double-bonding reduction where 2-isopropylphenol was produced. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.122

文献信息

• Cp*Co(III)-Catalyzed Dearomative [3 + 2] Spiroannulation of 2-Alkenylphenols with Ynamides via C–H Activation
  作者：Peng-Peng Lin、Xiang-Lei Han、Guo-Hua Ye、Ji-Lin Li、Qingjiang Li、Honggen Wang

  DOI：10.1021/acs.joc.9b01750

  日期：2019.10.18

  An oxidative [3 + 2] C-H spiroannulation reaction of 2-alkenylphenols with ynamides has been developed toward the synthesis of spiro[4,5]decane derivatives. This dearomative reaction employs earth-abundant cobalt as the metal catalyst and occurs under rather mild reaction conditions (room temperature). The use of ynamides confers unique reactivity and exclusive regioselectivity. The products bearing

  已经开发了2-烯基苯酚与乙酰胺的氧化[3 + 2] CH螺环合成反应，用于合成螺[4,5]癸烷衍生物。该脱芳香反应使用富含稀土的钴作为金属催化剂，并且在相当温和的反应条件下（室温）进行。乙酰胺的使用赋予其独特的反应性和排他性区域选择性。带有全碳四元立体异构中心的产物通常以高收率构建，并观察到良好的官能团耐受性。进行了实验机理研究，并提出了可能的反应机理。
• Palladium(II)-Catalyzed Annulation between <i>ortho</i>-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
  作者：Noelia Casanova、Karina P. Del Rio、Rebeca García-Fandiño、José L. Mascareñas、Moisés Gulías

  DOI：10.1021/acscatal.6b00739

  日期：2016.5.6

  2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-like products through a pathway involving a β-hydrogen elimination step. Computational studies suggest that the square planar

  2-烯基酚与丙二烯反应，在催化量的 Pd(II) 和 Cu(II) 处理后，以高收率和非常好的区域和非对映选择性得到苯并氧杂环庚烷产品。这与使用 Rh 催化剂获得的结果形成对比，后者通过涉及 β-氢消除步骤的途径提供类色烯产物。计算研究表明，钯的方形平面几何形状对于促进形成 oxepine 产品所需的还原消除过程至关重要。
• Piperidine pyrazoles as fungicides
  申请人：Hillebrand Stefan

  公开号：US10004232B2

  公开（公告）日：2018-06-26

  The invention relates to heteroarylpiperidine and -piperazine derivatives of formula (I) to agrochemically active salts thereof, to their use and also to methods and compositions for controlling phytopathogenic harmful fungi in and/or on plants or in and/or on seed of plants, to methods for producing such compositions and to treated seed, and also to the use thereof for controlling phytopathogenic harmful plants in agriculture, horticulture and forestry, in animal health, in materials protection and also in the household and hygiene sector. The present invention further relates to a method for producing heteroarylpiperidine and -piperazine derivatives.

  本发明涉及式 (I) 的杂芳基哌啶和哌嗪衍生物 本发明涉及其农用化学活性盐，涉及其用途，还涉及用于控制植物体内和/或植物上或植物种子中和/或植物种子上的植物病原性有害真菌的方法和组合物，涉及生产此类组合物的方法和处理过的种子，还涉及其在农业、园艺和林业、动物健康、材料保护以及家庭和卫生领域中用于控制植物病原性有害植物的用途。本发明还涉及一种生产杂芳基哌啶和哌嗪衍生物的方法。
• Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
  作者：Andrés Seoane、Noelia Casanova、Noelia Quiñones、José L. Mascareñas、Moisés Gulías

  DOI：10.1021/ja5034952

  日期：2014.5.28

  Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.
• Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives
  作者：Xu-Ge Liu、Shang-Shi Zhang、Chun-Yong Jiang、Jia-Qiang Wu、Qingjiang Li、Honggen Wang

  DOI：10.1021/acs.orglett.5b02728

  日期：2015.11.6

  Cp*Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.