3-羟基-2-甲基环己-2-烯-1-酮 | 32774-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-2-甲基环己-2-烯-1-酮
• 英文名称: 3-hydroxy-2-methyl-cyclohex-2-enone
• 英文别名: 3-Hydroxy-2-methylcyclohex-2-en-on；3-hydroxy-2-methylcyclohex-2-en-1-one；2-Methyldihydroresorcinol；2-methyl-3-hydroxy-cyclohex-2-en-1-one；2-Cyclohexen-1-one, 3-hydroxy-2-methyl-
• CAS: 32774-63-3
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: NHMJKYVPXYBHSL-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C
• 沸点：
  226.9±40.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-羟基-2-甲基环己-2-烯-1-酮 在 碘 、 sodium acetate 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 methyl 2-methyl-3-oxo-1-cyclohex-1-enecarboxylate
  参考文献：
  名称：

  通过CH键活化对高取代的烯丙醇进行光氧化还原催化的异构化。

  摘要：

  γ-羰基取代的烯丙醇的光氧化还原催化异构化为其相应的羰基化合物是首次通过CH键进行活化。这种催化的氧化还原中性过程导致了1,4-二羰基化合物的合成。值得注意的是，带有四取代烯烃的烯丙基醇也可以转化成它们相应的羰基化合物。密度泛函理论计算表明，烯丙醇的γ位上的羰基有利于形成具有较高垂直电子亲和力的相应烯丙基醇自由基，这有助于完成光氧化还原催化循环。

  DOI：

  10.1002/anie.202000743
• 作为产物：
  描述：

  2-((phenylamino)methylene)cyclohexane-1,3-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以71%的产率得到3-羟基-2-甲基环己-2-烯-1-酮
  参考文献：
  名称：

  Ziegler, Erich; Wolfbeis, Otto S.; Trummer, Iris, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 1, p. 105 - 107

  摘要：

  DOI：

文献信息

• Nitrogen Fixation: Synthesis of Heterocycles Using Molecular Nitrogen as a Nitrogen Source
  作者：Miwako Mori、Masaya Akashi、Masanori Hori、Katsutoshi Hori、Mayumi Nishida、Yoshihiro Sato

  DOI：10.1246/bcsj.77.1655

  日期：2004.9

  Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium–nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(OiPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium–nitrogen complexes. Although the structures of the titanium–nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.

  过渡金属固氮是一个迷人的过程。我们之前已经报道过使用Yamamoto报道的钛-氮配合物将分子氮引入有机化合物的方法。我们开发了一种新的钛催化氮化过程，使用TiCl4在过量Li和TMSCl的存在下进行。在这种反应中，可以使用1大气压的氮气，反应在室温下进行。这个过程非常简单。将TiCl4或Ti(OiPr)4（1 equiv.）、Li（10 equiv.）和TMSCl（10 equiv.）的THF溶液在氮气气氛下在室温下搅拌过夜，得到钛-氮配合物。尽管钛-氮配合物的结构尚未确定，但它们可能由N(TMS)3、X2TiN(TMS)2和XTi=NTMS组成。使用这种方法，可以通过钛配合物作为定量反应的单锅反应，以良好至中等的收率合成各种杂环化合物，如吲哚、喹啉、吡咯、吡咯啉和吲哚啉衍生物。此外，使用分子氮作为氮源合成了monomorine I和pumiliotoxin C。这种方法进一步扩展，用于使用催化量的钛配合物合成杂环化合物；此外，以高收率获得了吲哚和吡咯衍生物。
• A convenient, practical synthesis of substituted resorcinols: synthesis of DB-2073 and olivetol
  作者：Atul S. Kotnis

  DOI：10.1016/0040-4039(91)80801-c

  日期：1991.7

  A wide variety of easily accesible 1,3-cyclohexanediones are readily transformed to substituted dimethyl resorcinols with iodine and methanol.

  各种容易接近的1,3-环己二酮很容易被碘和甲醇转化为取代的二甲基间苯二酚。
• [EN] HERBICIDAL PYRIDAZINONES<br/>[FR] PYRIDAZINONES HERBICIDES
  申请人：DU PONT

  公开号：WO2014031971A1

  公开（公告）日：2014-02-27

  Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, INSERT FORMULA 1 HERE wherein A is a radical selected from the group consisting of INSERT FORMULA A-1, A-2, A-3, A-4, A-5, A-6 AND A-7 HERE and B1, B2, B3, T, R1, R2, R3, R3A, R4, R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

  披露了公式1的化合物，包括所有立体异构体、N-氧化物和盐，INSERT FORMULA 1 HERE 其中A是选择自以下组的自由基：INSERT FORMULA A-1, A-2, A-3, A-4, A-5, A-6 AND A-7 HERE，B1, B2, B3, T, R1, R2, R3, R3A, R4, R5, R6, R7, R8, R9, R10, R11, R12和R13如披露中定义。还披露了包含公式1化合物的组合物，以及控制不需要的植被的方法，包括将不需要的植被或其环境与有效量的化合物或本发明的组合物接触。
• SULFOXYIMINO-SUBSTITUTED BENZOYL DERIVATIVE AND HERBICIDE
  申请人：Tamai Tetsuo

  公开号：US20110144345A1

  公开（公告）日：2011-06-16

  The benzoyl derivative of the present invention is represented by formula (I) (in the formula, E represents an alkoxy group, an alkoxycarbonyl group or the like, R 1 represents a halogen atom, an organic group or the like, p represents an integer of 0 to 3, R 2 and R 3 each independently represents an alkyl group or the like, Q represents a group selected from the groups represented by the following formulas Q1 to Q8: (in the formula, * represents binding site, G represents oxygen atom or the like), R 4 to R 5 , R 8 to R 13 represents hydrogen atom, an alkyl group or the like), R 6 represents cyano group or the like, X represents —C(R 12 )(R 13 )— or —N(R 12 )—, Y represents oxo group, an alkyl group or the like, m represents an integer of 0 to 4)) or salt thereof.

  本发明的苯甲酰衍生物由以下式（I）表示： （在该式中，E代表烷氧基、烷氧羰基或类似物，R1代表卤原子、有机基或类似物，p代表0至3的整数，R2和R3各自独立代表烷基或类似物，Q代表从以下式Q1至Q8所代表的群中选择的群： （在该式中，*代表结合位点，G代表氧原子或类似物），R4至R5，R8至R13代表氢原子、烷基或类似物），R6代表氰基或类似物，X代表—C(R12)(R13)—或—N(R12)—，Y代表氧基、烷基或类似物，m代表0至4的整数））或其盐。
• 2,3-DIPHENYL-VALERONITRILE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND USE THEREOF AS HERBICIDES AND PLANT GROWTH REGULATORS
  申请人：Mosrin Marc

  公开号：US20140235446A1

  公开（公告）日：2014-08-21

  The compounds of the formula (I) in which L represents a radical of the formula and A 1 , B 1 and A 2 and B 2 are as defined in Claim 1, are suitable as herbicides for the control of harmful plants or as plant growth regulators. The compounds can be prepared by the process of Claim 12.

  式(I)中L代表式的基团，A1、B1、A2和B2如权利要求1所定义，适用于作为除草剂用于控制有害植物或作为植物生长调节剂。这些化合物可以通过权利要求12所述的方法制备。

表征谱图