4,4-二甲基萘-1-酮 | 16020-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4,4-二甲基萘-1-酮
• 中文别名: 4,4-二甲基萘-1(4H)-酮
• 英文名称: 1-Oxo-4.4-dimethyl-1.4-dihydro-naphthalin
• 英文别名: 4,4-Dimethylnaphthalen-1(4h)-one；4,4-dimethylnaphthalen-1-one
• CAS: 16020-16-9
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: LVCLGJPQSZTOBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-二甲基萘-1-酮 在 四氯化碳 、 溴 作用下， 生成 2-bromo-4,4-dimethyl-4H-naphthalen-1-one
  参考文献：
  名称：

  The Dienone—Phenol Rearrangement

  摘要：

  DOI：

  10.1021/ja01202a022
• 作为产物：
  描述：

  4,4-二甲基-3,4-二氢-2H-萘-1-酮 在 sodium hydroxide 、 sodium hydride 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 4,4-二甲基萘-1-酮
  参考文献：
  名称：

  Structure-activity relationships among DNA gyrase inhibitors. Synthesis and biological evaluation of 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acids as 1-carba bioisosteres of oxolinic acid

  摘要：

  A series of oxolinic acid analogues was synthesized in an attempt to evaluate the role, if any, played by the N-1 atom in putative modes of action of antimicrobial DNA gyrase inhibitors. Carba analogues were prepared because these have no possibility of an internal resonance contribution of the nitrogen atom and yet could otherwise satisfy electronic requirements of putative modes of action. Successful routes were developed involving Friedel-Craft's cycloaddition of suitable aromatic compounds with 4,4-dimethylbutyrolactone, followed by ethoxycarbonylation, oxidation with dichlorodicyanobenzoquinone, and careful saponification. The gem-dimethyl group of these analogues prevents aromatization at the cost of nonplanarity. Only the unsubstituted parent compound, 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acid, possessed any appreciable antimicrobial activity in vitro. This may be due to a different mode of action, however, since gave no measurable inhibition of DNA gyrase in vitro. Thus, the N-1 atom plays a significant role in enzymic and bacteriological inhibition that cannot be compensated for by the presence of C-6 oxygen atoms.

  DOI：

  10.1021/jm00369a013

文献信息

• Substituent effects on the rate of carbene formation by the pyrolysis of rigid aryl substituted diazomethanes
  作者：Naresh C Mathur、Miles S Snow、Kent M Young、James A Pincock

  DOI：10.1016/s0040-4020(01)96390-2

  日期：1985.1

  Rate constants for the pyrolysis of 1-diazo-4,4-dimethyl-1,4-dihydronaphthalenes, 4a–4e, have been measured in methanol : 6% triethylamine. In contrast to non-rigid cases, like diphenyldiazomethanes, where all para substituents show a rate increase compared to hydrogen, these rates show a linear Hammett correlation for para substituents with σ+ = — 0.84. This observation is rationalized by a non-linear

  1-重氮-4,4-二甲基-1,4-二氢萘（4a-4e）的热解速率常数已在甲醇：6％三乙胺中测定。与非刚性情况（如二苯基重氮甲烷）相反，在该情况下，所有对位取代基均比氢显示出速率增加，这些速率显示出对位取代基的线性Hammett相关性，其中σ + =-0.84。通过非线性过程合理化该观察结果，该过程涉及直接导致卡宾基态单峰态的氮的流失17。然后将该卡宾捕集，得到醚11。
• Asymmetric Weitz−Scheffer Epoxidation of α,β-Enones by Optically Active Hydroperoxides: Control of Enantioselectivity through Metal-Coordinated or Hydrogen-Bonded Templates
  作者：Waldemar Adam、Paraselli Bheema Rao、Hans-Georg Degen、Chantu R. Saha-Möller

  DOI：10.1002/1099-0690(200202)2002:4<630::aid-ejoc630>3.0.co;2-y

  日期：2002.2

  The enantioselective epoxidation of the α,β-enones 1 with the optically active hydroperoxides (−)-(S)-2, catalyzed by the bases KOH or DBU, affords the enantiomerically enriched oxo epoxides 3 in high yields and with good enantioselectivities (up to 90% ee for KOH and up to 72% ee for DBU). The preparatively useful feature of this asymmetric epoxidation is the fact that opposite senses of enantioselectivity

  α,β-烯酮 1 与旋光氢过氧化物 (-)-(S)-2 的对映选择性环氧化，由碱 KOH 或 DBU 催化，以高产率和良好的对映选择性（高达KOH 高达 90% ee，DBU 高达 72% ee）。这种不对称环氧化的制备性有用特征是这样一个事实，即使用相同的光学活性氢过氧化物和相同的前手性烯酮底物观察到相反意义的对映选择性。因此，CH3CN 中的 KOH 通过优先的 Si 面攻击从查耳酮 1a 提供 (αS,βR)-环氧化物 3a，而甲苯中的 DBU 通过有利的 Re-face 从该烯烃选择性地提供 (αR,βS)-环氧化物 3a攻击。提出模板结构，通过八面体连接 K+ 或氢键 DBUH+ 铵离子保持在一起，解释观察到的对映选择性。对映选择性的意义和程度由碱衍生的模板 K+ 和 DBUH+ 试剂、手性过氧化物阴离子氧供体和前手性烯酮底物之间的空间相互作用决定。
• Carbon-13-proton coupling constants in carbocations. 4. Conformations of internal cyclopropylcarbinyl cations (benzobicyclo[4.1.0]heptyl cations) and their rearrangements to naphthalenium cations
  作者：David P. Kelly、D. Ralph Leslie、Bradley D. Smith

  DOI：10.1021/ja00315a038

  日期：1984.2

  Determination de la conformation des cations formes par ionisation des dimethyl-1,1 methano-3,4 tetrahydro-1,2,3,4 naphtalene-2ols substitues en 2, a l'aide d'une methode basee une equation de difference de constante de couplage

  Determination de la conformation des cations formes par ionisation des dimethyl-1,1 methano-3,4 tetrahydro-1,2,3,4naphtalene-2ols substitues en 2, a l'aide d'une methode basee une equation de difference de君士坦丁堡
• The bicycle rearrangement. 5. Relationship to the di-.pi.-methane rearrangement and control by bifunnel distortion. Mechanistic and exploratory organic photochemistry
  作者：Howard E. Zimmerman、Ronda E. Factor

  DOI：10.1021/ja00530a039

  日期：1980.5
• Alumina-catalyzed rreactions of hydroxyarenes and hydroaromatic ketones. I. Reactions of 1-naphthol with methanol
  作者：LeRoy H. Klemm、Joseph Shabtai、Dennis Riley Taylor

  DOI：10.1021/jo01268a036

  日期：1968.4