(6-methoxy-2-naphthyl) isopropyl ketone | 179930-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (6-methoxy-2-naphthyl) isopropyl ketone
• 英文别名: 1-(6-methoxy-[2]naphthyl)-2-methyl-propan-1-one；1-(6-Methoxy-[2]naphthyl)-2-methyl-propan-1-on；1-(6-Methoxy-2-naphthalenyl)-2-methyl-1-propanone；1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-one
• CAS: 179930-43-9
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: DNZDEPFFHZREHA-UHFFFAOYSA-N

物化性质

• 熔点：
  57–58°C
• 沸点：
  213-214 °C(Press: 15 Torr)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (6-methoxy-2-naphthyl) isopropyl ketone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以70%的产率得到1-(6-methoxy-2-naphthyl)-2-methyl-propanol
  参考文献：
  名称：

  C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors

  摘要：

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.016
• 作为产物：
  描述：

  1-(6-methoxy-2-naphthyl)-2-methyl-propanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(6-methoxy-2-naphthyl) isopropyl ketone
  参考文献：
  名称：

  三取代甲烷和手性叔α-羟醛（四取代甲烷的可能中间体）的合成方法†

  摘要：

  据报道，一系列含有芳基和杂芳基环的三取代甲烷，以及在中心甲烷碳和苯环之间的硫间隔基。在一种具有高对映选择性的不对称四取代甲烷的方法中，通过在二取代烯烃上进行无尖锐的二羟基化反应，然后对伯醇进行化学选择性氧化，合成了手性叔α-羟基醛。

  DOI：

  10.1039/c3ra41826j

文献信息

• Highly Selective and Efficient Conversion of Alkyl Aryl and Alkyl Cyclopropyl Ketones to Aromatic and Cyclopropane Carboxylic Acids by Aerobic Catalytic Oxidation: A Free-radical Redox Chain Mechanism.
  作者：Francesco Minisci、Francesco Recupero、Francesca Fontana、Hans-René Bjørsvik、Lucia Liguori

  DOI：10.1055/s-2002-22706

  日期：——

  An efficient and convenient method has been developed for the oxidation of aryl alkyl and cyclopropyl alkyl ketones to aromatic and cyclopropane carboxylic acids by molecular oxygen at atmospheric pressure, catalysed by Mn(NO 3 ) 2 in combination with Co(NO 3 ) 2 or Cu(NO 3 ) 2 . This simple, cheap and highly selective process has a general character for the synthesis of carboxylic acids and it is

  已开发出一种在常压下通过分子氧在 Mn(NO 3 ) 2 与 Co(NO 3 ) 2 或 Cu 的组合催化下将芳基烷基和环丙基烷基酮氧化成芳香族和环丙烷羧酸的高效便捷方法。 （否 3） 2．这种简单、廉价和高选择性的方法具有合成羧酸的通用特性，特别适合工业应用。
• Deacetylative Amination of Acetyl Arenes and Alkanes with C–C Bond Cleavage
  作者：Kengo Hyodo、Genna Hasegawa、Hiroya Maki、Kingo Uchida

  DOI：10.1021/acs.orglett.9b00807

  日期：2019.4.19

  The Brønsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C–C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction

  描述了由Brønsted酸催化的C–C键断裂，由乙酰基芳烃和烷烃合成伯胺。尽管从乙酰基向胺的转化传统上需要多个步骤，但是本文所述的使用肟试剂作为氨基源的方法直接通过多米诺转肟化/贝克曼重排/品纳反应实现了转化。该方法还适用于γ-氨基丁酸的合成，如巴克洛芬和咯利普兰。
• [EN] METHOD OF ACYLATING AN AROMATIC COMPOUND<br/>[FR] PROCÉDÉ D'ACYLATION D'UN COMPOSÉ AROMATIQUE
  申请人：DSM IP ASSETS BV

  公开号：WO2015001032A1

  公开（公告）日：2015-01-08

  The present invention relates to a method of acylating a substituted aromatic compound. The substituted aromatic compound is reacted with an acylating agent in the presence of a macroreticular sulfonic acid ion exchange resin having a water-to-phenol shrinkage between 25 % and 40 %. The method is very advantageous in that the resin is deactivated much less than other resins without a fast drop in conversion and selectivity in the reaction.

  本发明涉及一种酰化取代芳香化合物的方法。所述取代芳香化合物在存在具有水对苯酚收缩率在25%至40%之间的大孔硫酸树脂的情况下与酰化试剂发生反应。该方法非常有利，因为相较于其他没有在反应中快速降解转化率和选择性的树脂，该树脂的失活程度要小得多。
• Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor
  作者：Akio Ojida、Nobuyuki Matsunaga、Tomohiro Kaku、Akihiro Tasaka

  DOI：10.1016/j.tetasy.2004.02.035

  日期：2004.5

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.
• Horeau; Jacques, Bulletin de la Societe Chimique de France, 1947, p. 61,62
  作者：Horeau、Jacques

  DOI：——

  日期：——