1-(4-methyl-naphthalen-2-yl)-ethanone | 67757-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-methyl-naphthalen-2-yl)-ethanone
• 英文别名: 1-(4-methylnaphthalen-2-yl)ethanone；4-Methyl-2-acetonaphthalene；1-Methyl-3-acetyl-naphthalin；1 Methyl-3-acetylnaphthalin
• CAS: 67757-60-2
• 化学式: C₁₃H₁₂O
• 分子量: 184.238
• InChiKey: FHWKKTPLAUFLDM-UHFFFAOYSA-N

物化性质

• 熔点：
  39 °C
• 沸点：
  325.4±11.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-methyl-2-naphthalenecarboxylic acid 在 吡啶 四氯化碳 、 草酰氯 、 乙醇 、 硫酸 、 magnesium 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 9.0h， 生成 1-(4-methyl-naphthalen-2-yl)-ethanone
  参考文献：
  名称：

  Chatterjea, Jnanendra N.; Lal, Siddheshwar; Jha, Udar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 4, p. 264 - 267

  摘要：

  DOI：

文献信息

• Oxy Effects on the Platinum-Catalyzed Carbo- and Oxacyclizations of 2-Oxiranyl-1-(1-oxyalk-2-ynyl)benzenes
  作者：Rupsha Chaudhuri、Samir Kundlik Pawar、Kamalkishore Pati、Rai-Shung Liu

  DOI：10.1002/adsc.201200187

  日期：2012.8.13

  We report new platinum-catalyzed protocols for the synthesis of carbocycles and oxacycles from 2-oxiranyl-1-(1-oxyalk-2-ynyl)benzenes. For 1,2,2-trisubstituted epoxides bearing an acyloxy group, their platinum-catalyzed cyclizations proceed through an initial 1,3-acyloxy shift, followed by an intramolecular attack of an allenyl acetate at the carbonyl group, ultimately giving 2-naphthyl ketones through

  我们报告了从2-环氧乙烷基-1-（1-氧代烷-2-炔基）苯合成碳环和氧环的新铂催化方案。对于带有酰氧基的1,2,2-三取代的环氧化物，其铂催化的环化过程是通过最初的1,3-酰氧基转移进行的，随后是乙酸烯丙酯在羰基上的分子内侵蚀，最终生成2-萘基酮通过选择性的1,2-烷基转移。带有甲硅烷氧基的1，1-二取代的环氧化物进行氧环化，得到具有高非对映选择性的双环缩酮。
• The Baylis–Hillman acetates in organic synthesis: Unprecedented sodium nitrite induced intramolecular Friedel–Crafts cyclization of secondary nitro compounds
  作者：Deevi Basavaiah、Daggula Mallikarjuna Reddy

  DOI：10.1039/c4ra03573a

  日期：——

  Unprecedented sodium nitrite mediated intramolecular Friedel–Crafts cyclization of alkyl (E)-2-arylidene-4-nitroalkanoates and (E)-3-arylidene-5-nitroalkan-2-ones derived from Baylis–Hillman acetates, providing a facile protocol for synthesis of naphthalenes, phenanthrenes, and carbazoles has been described.

  前所未有的亚硝酸钠介导的Bayes-Hillman乙酸酯衍生的烷基（E）-2-芳基亚烷基-4-硝基链烷酸酯和（E）-3-芳基亚烷基5-硝基醛烷-2-酮的分子内Friedel-Crafts环化已经描述了萘，菲和咔唑的合成。
• Process for producing 1,3-naphthalenedicarboxylic acid
  申请人：Ogawa Hiroshi

  公开号：US20050187403A1

  公开（公告）日：2005-08-25

  1,3-Naphthalenedicarboxylic acid is produced by oxidizing 1,3-dialkylnaphthalene in a liquid-phase with an oxygen-containing gas in the presence of a C 2 -C 6 lower aliphatic carboxylic acid solvent and a catalyst comprising a heavy metal and a bromine compound. By regulating the ratio of the total number of bromine atoms fed into a reaction system to the total number of 1,3-dialkylnaphthalene molecules fed into the reaction system within a specific range, 1,3-naphthalenedicarboxylic acid is efficiently produced with low costs. Using 1,3-dimethylnaphthalene, as the starting 1,3-dialkylnaphthalene, which is produced by isomerizing dimethylnaphthalenes in a liquid phase in the presence of a catalyst comprising hydrogen fluoride and boron trifluoride together with a C 5 -C 10 alicyclic saturated hydrocarbon having a five-membered or six-membered ring structure, a highly pure 1,3-naphthalenedicarboxylic acid is efficiently produced.

  1,3-萘二甲酸是通过在液相中，在含氧气体的存在下，在C2-C6低级脂肪酸溶剂和重金属和溴化物催化剂的存在下氧化1,3-二烷基萘制成的。通过在特定范围内调节进入反应系统的总溴原子数与进入反应系统的总1,3-二烷基萘分子数的比例，以低成本高效地生产1,3-萘二甲酸。使用1,3-二甲基萘作为起始1,3-二烷基萘，通过在液相中，在氢氟酸和三氟化硼催化剂和具有五元环或六元环结构的C5-C10脂环饱和碳氢化合物的存在下异构化二甲基萘，高纯度的1,3-萘二甲酸被高效地制成。
• A 1,3-carbonyl shift in the platinum-catalyzed aromatization of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes
  作者：Rupsha Chaudhuri、Arindam Das、Hsin-Yi Liao、Rai-Shung Liu

  DOI：10.1039/c002660c

  日期：——

  A platinum-catalyzed reaction involving new aromatization/1,3-carbonyl shift cascade of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes is reported. This skeletal rearrangement is mechanistically significant because it involves a remarkable 1,3-carbonyl shift to complete the aromatization and to regenerate the catalyst.

  据报道，铂催化的反应涉及新的2-环氧-1-（甲氧基烷基-2-炔基）苯的芳构化/ 1,3-羰基转移级联。该骨架重排在机械上是重要的，因为它涉及显着的1，3-羰基转移以完成芳构化并再生催化剂。
• Pt- and Au-catalyzed oxidative cyclization of 2-ethenyl-1-(prop-2′-yn-1′-ol)benzenes to naphthyl aldehydes and ketones: catalytic oxidation of metal-alkylidene intermediates using H₂O and H₂O₂
  作者：Bhanu Pratap Taduri、Shariar Md. Abu Sohel、Hsin-Mei Cheng、Guan-You Lin、Rai-Shung Liu

  DOI：10.1039/b700659d

  日期：——

  2-Ethenyl-1-(prop-2′-yn-1′-ol)benzenes was cyclized through catalytic oxidation with PtCl2/CO/H2O and PEt3AuCl/H2O2; the metal–naphthylidene intermediates were identified and oxygenated with water and H2O2, respectively; for the efficiency of cyclization, the Au catalytic system is superior to that of the PtCl2-catalysis because of its compatibility toward diverse alcohol substrates including both internal alkynes and terminal alkynes.

  用PtCl2/CO/H2O和PEt3AuCl/H2O2催化氧化环化2-乙烯基-1-(prop-2-yn-1-ol)苯；金属-亚萘基中间体被鉴定并分别用水和H2O2氧化；就环化效率而言，Au 催化体系优于 PtCl2 催化，因为它与多种醇底物（包括内部炔烃和末端炔烃）相容。