1-乙酰基-4-甲基-3-环己烯-1-醇 | 82873-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-乙酰基-4-甲基-3-环己烯-1-醇
• 英文名称: 1-acetyl-4-methyl-3-cyclohexen-1-ol
• 英文别名: 1-(1-Hydroxy-4-methylcyclohex-3-en-1-yl)ethanone
• CAS: 82873-58-3
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: LHHMWXJBVDAALF-UHFFFAOYSA-N

物化性质

• 沸点：
  250.9±40.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-乙酰基-4-甲基-3-环己烯-1-醇 在 六甲基磷酰三胺 、 正丁基锂 、 sodium 作用下， 以 乙醚 、 xylene 为溶剂， 反应 52.5h， 生成 萜品油烯
  参考文献：
  名称：

  1-Acetyl-4-methyl-3-cyclohexen-1-ol，合成环状单萜的有用前体

  摘要：

  摘要 报道了从标题化合物 7 合成单环单萜：p-mentha-1,8-dien-4-ol (1)、terpinolene (4) 和 p,α-二甲基苯乙烯 (5)，作为常见的前体。 .

  DOI：

  10.1080/00397919208021634
• 作为产物：
  描述：

  2,4-Dinitro-benzoic acid 1-acetyl-4-methyl-cyclohex-3-enyl ester 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 生成 1-乙酰基-4-甲基-3-环己烯-1-醇
  参考文献：
  名称：

  α-Acetyl- and α-Cyanovinyl 2,4-Dinitrophenyl Carboxylate as Useful Ketene Equivalents for the Diels-Alder Reaction

  摘要：

  针对Diels-Alder反应，已开发出两种乙烯酮等价物（5和35）。与更为传统的乙酰氧基丙烯腈相比，这些二烯亲和物表现出显著提高的反应活性。在温和及中至高产率条件下，环加成物可转化为所需的酮。

  DOI：

  10.1055/s-1997-5775

文献信息

• Highly Efficient Synthesis of the Natural Spiro-Terpenoid (±)-Andirolactone
  作者：Arturo Orduña、L. Gerardo Zepeda、Joaquín Tamariz

  DOI：10.1055/s-1993-25866

  日期：——

  A synthesis of the natural terpenoid spirolactone (±)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl-4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of olefin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46 % overall yield.

  描述了一种天然萜类旋内酯(±)-安地内酯 (1) 的合成。二甲基马洛酸酯 (9) 与1-乙酰-4-甲基-3-环己烯-1-醇 (3) 进行缩合，后者是通过烯烃5和异戊烯(4)的Diels-Alder反应制备的，随后对所得的旋内酯10进行热脱羧反应，总体收率为46%。
• Regioselectivity of Diels-Alder additions of 1-acetylvinyl arenecarboxylates.
  作者：Raul Aguilar、Alicia Reyes、Joaquín Tamariz、Jean-Luc Birbaum

  DOI：10.1016/s0040-4039(01)81009-1

  日期：1987.1

  The Diels-Alder addition of “captodative” dienophiles 1-acetylvinyl arenecarboxylates , and to 1- and 2-substituted dienes was found highly regioselective. The rate and regioselectivity of this reaction were improved by Lewis acid catalysis.

  的狄尔斯-阿德耳加成“推拉”的亲二烯体1-acetylvinyl arenecarboxylates ，和至1-和2-取代的二烯，发现高度选择性。该反应的速率和区域选择性通过路易斯酸催化得到改善。
• The [2,3] Sigmatropic Reaction of Acetonyl Allyl Ethers, a new method for preparing certain 2-hydroxyketones
  作者：Alan F. Thomas、Ren�e Dubini

  DOI：10.1002/hlca.19740570721

  日期：1974.11.6

  A new [2] [3] sigmatropic rearrangement is described, enabling the conversion of acetonyl allyl ethers to 3-hydroxy-5-en-2-ones.

  描述了新的[2] [3]σ重排，可将丙酮基烯丙基醚转化为3-羟基-5-烯-2-酮。
• Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides
  作者：Omar Merino、Blanca M. Santoyo、Luisa E. Montiel、Hugo A. Jiménez-Vázquez、L. Gerardo Zepeda、Joaquín Tamariz

  DOI：10.1016/j.tetlet.2010.05.034

  日期：2010.7

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.
• Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones
  作者：Masahiro Egi、Yuya Ota、Yuka Nishimura、Kaori Shimizu、Kenji Azechi、Shuji Akai

  DOI：10.1021/ol401824v

  日期：2013.8.16

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.