3-Methoxyphenyl 1-naphthyl ketone | 109251-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Methoxyphenyl 1-naphthyl ketone
• 英文别名: (3-methoxy-phenyl)-[1]naphthyl ketone；(3-Methoxy-phenyl)-[1]naphthyl-keton；(3-Methoxyphenyl)(naphthalen-1-yl)methanone；(3-methoxyphenyl)-naphthalen-1-ylmethanone
• CAS: 109251-88-9
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: PJJMZIDNKIRXFK-UHFFFAOYSA-N

物化性质

• 沸点：
  260-261 °C(Press: 24 Torr)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3-Methoxy-phenyl)-(1)naphthyl-carbinol 在 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 46.0h， 以72%的产率得到3-Methoxyphenyl 1-naphthyl ketone
  参考文献：
  名称：

  Na-promoted aerobic oxidation of alcohols to ketones

  摘要：

  Aerobic oxidation of a number of diaryl and arylalkyl carbinols to ketones was promoted by Na in THF at room temperature with up to 99% yield. This new oxidation method is also selective with good efficiency for the oxidation of benzylic secondary alcohols but not for a primary alcohol or nonbenzylic secondary alcohols. Under nitrogen, a catalytic amount of Ni or transition metal halides such as COCl3, FeCl3, and NiCl3 in combination with Na was also found to conduct a dehydrogenation of a secondary alcohol to the corresponding ketone in high yield at room temperature. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.079

文献信息

• Benzylation via Tandem Grignard reaction —iodotrimethylsilane (TMSI) mediated reduction
  作者：Eric J. Stoner、Darlene A. Cothron、Mary K. Balmer、Brian A. Roden

  DOI：10.1016/0040-4020(95)00659-v

  日期：1995.10

  initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI). A number of improvements over existing literature procedures are reported as well as previously unobserved dimenzations. Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not

  已经开发出允许大规模制备联芳基甲烷的方法。该方法包括通过芳基格氏试剂与羰基化合物的反应初始形成联芳基甲醇，随后用碘代三甲基硅烷（TMSI）还原。据报道，对现有文献方法以及先前未曾观察到的尺寸进行了许多改进。研究表明，在大多数取代基都不是杂芳族的情况下，只有3当量的TMSI会完全还原。单取代的链烷醇与TMSI反应，得到相应的碘化物。还报道了TMSI减少的机理研究。
• Carbonylative coupling reaction of organofluorosilanes with organic halides promoted by fluoride ion and palldium catalyst
  作者：Yasuo Hatanaka、Satoshi Fukushima、Tamejiro Hiyama

  DOI：10.1016/s0040-4020(01)88878-5

  日期：1992.1

  Palladium-catalyzed carbonylative cross coupling reaction of organofluorosilanes with organic halides was achieved in the presence of fluoride ion and an atmospheric pressure of carbon monoxide. Alkenyl- or arylfluorosilanes effectively underwent this reaction with alkenyl or aryl iodides in moderate to good yields. Thus, highly functionalized ketones are readily available without protection of reactive

  在氟离子和一氧化碳的大气压下，实现了有机氟硅烷与有机卤化物的钯催化羰基交叉偶联反应。烯基-或芳基氟硅烷与烯基或芳基碘化物有效地进行该反应，产率中等至良好。因此，在不保护反应性官能团例如醛，酮，酯，腈和醇的情况下，容易获得高度官能化的酮。为了顺利生成酮，必须使用有机氟硅烷。与芳基碘化物反应后，四芳基硅烷（如芳基（三甲基）硅烷）代替芳酰氟。
• Hatanaka, Yasuo; Hiyama, Tamejiro, Chemistry Letters, 1989, p. 2049 - 2052
  作者：Hatanaka, Yasuo、Hiyama, Tamejiro

  DOI：——

  日期：——
• The Behavior of 4-Methoxyphthalic Anhydride in Grignard Condensations
  作者：Russell Melby、Robert Crawford、Donald McGreer、Reuben B. Sandin

  DOI：10.1021/ja01596a068

  日期：1956.8
• HATANAKA, YASUO;HIYAMA, TAMEJIRO, CHEM. LETT.,(1989) N1, C. 2049-2052
  作者：HATANAKA, YASUO、HIYAMA, TAMEJIRO

  DOI：——

  日期：——