3-乙氧基-6-(丙-2-炔-1-基)环己-2-烯酮 | 1002353-89-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙氧基-6-(丙-2-炔-1-基)环己-2-烯酮
• 英文名称: 3-ethoxy-6-(prop-2-ynyl)cyclohex-2-enone
• 英文别名: 3-ethoxy-6-(prop-2-yn-1-yl)cyclohex-2-enone；3-Ethoxy-6-(prop-2-yn-1-yl)cyclohex-2-enone；3-ethoxy-6-prop-2-ynylcyclohex-2-en-1-one
• CAS: 1002353-89-0
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: KWOUOYZBVSWBNE-UHFFFAOYSA-N

物化性质

• 沸点：
  294.7±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙氧基-6-(丙-2-炔-1-基)环己-2-烯酮 在 Pd-BaSO₄ 、 氢氟酸 氢气 作用下， 生成 (6Z)-4,4a,5,8,9,10-hexahydro-3H-benzo[8]annulen-2-one
  参考文献：
  名称：

  形成稠合环辛烷或环己烷环的新方法

  摘要：

  已显示不对称烯丙基硅烷在共轭二烯酮上的分子内区域选择性加成使得可以容易地进入5-6、6-6、5-8和6-8双环系统。

  DOI：

  10.1016/s0040-4039(00)94902-5
• 作为产物：
  描述：

  1,3-环己二酮 在 正丁基锂 、 碘 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 3-乙氧基-6-(丙-2-炔-1-基)环己-2-烯酮
  参考文献：
  名称：

  通过路易斯酸促进环状2,6-烯醇的碳卤化反应方便地合成（E）-5-芳基（卤）亚甲基双环-[[2.2.2]辛-2-烯和-[2.2.1]庚-2-烯

  摘要：

  AbstractAn efficient synthesis of (E)‐5‐aryl(halo)methylenebicyclo[2.2.2]oct‐2‐enes is reported. Lewis acid‐promoted carbohalogenation of 4‐(3‐arylprop‐2‐ynyl)‐cyclohex‐2‐enols in dichloromethane proceeds rapidly to afford the exo‐methylene‐bridged bicycles in good yields. This method also provides an easy access to (E)‐5‐aryl(halo)methylenebicyclo[2.2.1]hept‐2‐enes from the five‐membered ring 2,6‐enynols. The reactions are procedurally simple and high yielding, producing the aryl(halo)methylene‐bridged bicycles in minutes under air and mild conditions.magnified image

  DOI：

  10.1002/adsc.201400671

文献信息

• Ring opening of cyclopropylketones induced by photochemical electron transfer
  作者：Janine Cossy、Nathalie Furet、Samir BouzBouz

  DOI：10.1016/0040-4020(95)00727-p

  日期：1995.10

  Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.

  根据环丙基酮的取代方式，光化学诱导的叔胺电子转移至环丙基酮会导致3-取代的环烷酮的形成或环扩产物。
• [EN] TARGETED COVALENT PROBES AND INHIBITORS OF PROTEINS CONTAINING REDOX-SENSITIVE CYSTEINES<br/>[FR] SONDES COVALENTES CIBLÉES ET INHIBITEURS DE PROTÉINES CONTENANT DES CYSTÉINES SENSIBLES À L'OXYDORÉDUCTION
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2014089546A1

  公开（公告）日：2014-06-12

  Covalent, irreversible small-molecule inhibitors that modify the sulfenyl form (i.e., sulfenic acid, RSOH and sulfenamide, RSNR'2) of therapeutically important proteins (particularly kinases and phosphatases) are disclosed, where the compositions include a compound having a substituted aryl or heterocyclic core structure that promotes binding interactions with a specific protein, and a nucleophilic reaction center (carbon, nitrogen, sulfur, or phosphorous) that is capable of forming a covalent bond with a sulfenic acid- or sulfenamide-modified cysteine residue in the protein. Methods for synthesizing these compounds are also disclosed, as well as methods of using them for determining the bioactivity of a chemical composition comprising an active compound toward a specific protein and for determining the potency of an inhibitor against a specific protein.

  揭示了用于修饰治疗重要蛋白质（特别是激酶和磷酸酶）的亚硫酰形式（即亚硫酸，RSOH和亚硫酰胺，RSNR'2）的共价、不可逆的小分子抑制剂，其中组合物包括具有取代芳基或杂环核结构的化合物，促进与特定蛋白质的结合相互作用，以及能够与蛋白质中的亚硫酸或亚硫酰胺修饰的半胱氨酸残基形成共价键的亲核反应中心（碳、氮、硫或磷）。还揭示了合成这些化合物的方法，以及使用它们确定包含活性化合物的化学组合物对特定蛋白质的生物活性以及确定抑制剂对特定蛋白质的效力的方法。
• C−H Amination in Synthesis:  An Approach to the Assembly of the B/C/D Ring System of Aconitine
  作者：Rosemary M. Conrad、J. Du Bois

  DOI：10.1021/ol702375r

  日期：2007.12.1

  A strategy for the preparation of aconitine is described that attempts to exploit chemoselective C-H amination and the electrophilic reactivity of oxathiazinane N,O-acetals for assembling the complex, polycyclic carbon framework of the natural product.

  描述了一种乌头碱的制备策略，该策略试图利用化学选择性的CH胺化和草并z嗪烷N，O-乙缩醛的亲电反应性来组装天然产物的复杂多环碳骨架。
• Gold-Catalyzed Cyclizations of Alkynyl Silyl Enol Ethers: An Easy Access to Bicyclo[3.2.1]octanone Derivatives
  作者：Amandine Carrër、Christophe Péan、Françoise Perron-Sierra、Olivier Mirguet、Véronique Michelet

  DOI：10.1002/adsc.201501135

  日期：2016.4.28

  efficient gold‐catalyzed cyclization reactions of alkynyl silyl enol ethers were successfully applied to the preparation of bicyclo[3.2.1]octanone derivatives. Accordingly, after optimization of the gold catalytic system, several bicyclic α,β‐unsaturated keto adducts were synthesized in good to excellent yields. The process followed a major 5‐exo cyclization via an anti addition of the silyl enol ether to

  炔基甲硅烷基烯醇醚的金催化高效环化反应已成功地用于制备双环[3.2.1]辛酮衍生物。因此，在优化金催化体系后，合成了几种双环α，β-不饱和酮加合物，收率良好至极佳。所遵循的过程的主要5-外型环化通过一个反加成的甲硅烷基烯醇醚的π共活化的中间体，将其通过一个氘掺入实验证实。甲6-内观察到甲硅烷基烯醇醚轴承供电子芳族基团的环化过程。
• A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction
  作者：Kay M. Brummond、Daitao Chen、Matthew M. Davis

  DOI：10.1021/jo8007258

  日期：2008.7.1

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.