3-(4-甲氧基苯基)-3,4-二氢萘-1(2H)-酮 | 61696-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-(4-甲氧基苯基)-3,4-二氢萘-1(2H)-酮
• 中文别名: 3-(4-甲氧基苯基)-1-四氢萘酮；3-(4-甲氧基苯基)-3,4-二氢-2H-萘-1-酮
• 英文名称: 3,4-dihydro-3-(4-methoxyphenyl)naphthalene-1(2H)-one
• 英文别名: 3-(4-methoxyphenyl)-1-tetralone；3-p-methoxyphenyl-1-tetralone；3-(4-methoxyphenyl)tetralone；3(4-methoxyphenyl)tetralin-1-one；1(2H)-Naphthalenone, 3,4-dihydro-3-(4-methoxyphenyl)-；3-(4-methoxyphenyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 61696-79-5
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: FKHGBDZJCJCGQW-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  391.6±31.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)
• 溶解度：
  溶于丙酮；氯仿；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-(4-甲氧基苯基)-3,4-二氢萘-1(2H)-酮 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 3-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  氟古马芬及其结构异构体的简单合成及生物学评价

  摘要：

  描述了氟考马芬1及其结构异构体的简单合成及其生物学特性。关键的合成策略包括Knoevenagel缩合，Grignard反应，分子内环环化和偶联反应。使用快速柱色谱法可轻松将Flocoumafen 1分离为顺式和反式形式。然后评估它们在体外对LPS诱导的NO生成的抑制作用和抗兴奋性毒性。发现反式氟尿嘧啶在体外浓度为10 µM时可有效抑制NO生成，而对培养的皮层神经元的神经毒性无明显影响。

  DOI：

  10.1007/s12039-010-0071-2
• 作为产物：
  描述：

  4-甲氧基亚苄基丙二酸二乙酯 在 氢氧化钾 、 PPA 、 Polyphosphoric acid (PPA) 、 硫酸 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 反应 15.0h， 生成 3-(4-甲氧基苯基)-3,4-二氢萘-1(2H)-酮
  参考文献：
  名称：

  Selvaraj, S.; Rajendran, A. S.; Arumugam, N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1047 - 1049

  摘要：

  DOI：

文献信息

• Synthesis and antitumor activity of 4-hydroxycoumarin derivatives
  作者：Jae-Chul Jung、Ji-Ho Lee、Seikwan Oh、Jae-Gon Lee、Oee-Sook Park

  DOI：10.1016/j.bmcl.2004.09.009

  日期：2004.11

  A series of 4-hydroxycoumarin derivatives was prepared and evaluated for antitumor activity. The key fragments were 2a-c, 5c, 12b, 13b, 17, and 18 which were prepared via dianion ring cyclization, Friedel-Crafts acylation, and Reformatsky reaction. Compound 20b showed the most potent antitumor activity among the total 12 derivatives and compounds 19a and 19b exhibited efficacy comparable to etoposide

  制备了一系列4-羟基香豆素衍生物，并评估了其抗肿瘤活性。关键片段是2a-c，5c，12b，13b，17和18，它们是通过二价环环化，Friedel-Crafts酰化和Reformatsky反应制备的。在全部12种衍生物中，化合物20b显示出最有效的抗肿瘤活性，并且化合物19a和19b显示出与依托泊苷体外抗肿瘤活性相当的功效。
• Simple synthesis and biological evaluation of flocoumafen and its structural isomers
  作者：Jae-Chul Jung、Soyong Jang、Seikwan Oh、Oee-Sook Park

  DOI：10.1007/s12039-010-0071-2

  日期：2010.11

  Simple synthesis and biological properties of flocoumafen 1 and its structural isomers are described. The key synthetic strategies involve Knoevenagel condensation, Grignard reaction, intramolecular ring cyclization and coupling reaction. Flocoumafen 1 was easily separated into cis and trans forms using flash column chromatography. They were then evaluated for suppression of LPS-induced NO generation

  描述了氟考马芬1及其结构异构体的简单合成及其生物学特性。关键的合成策略包括Knoevenagel缩合，Grignard反应，分子内环环化和偶联反应。使用快速柱色谱法可轻松将Flocoumafen 1分离为顺式和反式形式。然后评估它们在体外对LPS诱导的NO生成的抑制作用和抗兴奋性毒性。发现反式氟尿嘧啶在体外浓度为10 µM时可有效抑制NO生成，而对培养的皮层神经元的神经毒性无明显影响。
• Arynic condensation of ketone enolates—XIV
  作者：M. Essiz、G. Guillaumet、P. Caubere

  DOI：10.1016/s0040-4020(01)93740-8

  日期：1979.1

  Benzyne and 1-naphthyne (generated from the corresponding halogeno derivatives and the Complex Base NaNH2-ButONa) condense with α,β-unsaturated ketone enolates β-substituted by an aromatic ring and only enolisable in the α'-position, to lead to α-tetralones and/or indanones. The reaction path depends upon the nature of the ketone enolate and, less strongly, on the solvent. The reaction mechanism is

  苯炔和1- naphthyne（从相应的卤代衍生物和复基NaNH产生2 -Bu吨与α冷凝ONA），β不饱和酮的烯醇化物通过将芳族环β取代的并且仅在α'-位置烯醇化，至导致α-四氢萘酮和/或茚满酮。反应路径取决于酮烯醇化物的性质，而不太取决于溶剂。讨论了反应机理。这些反应构成许多α-四氢萘酮和茚满酮的新的简单有效的合成方法。
• Origin of Stereocontrol in Guanidine-Bisurea Bifunctional Organocatalyst That Promotes α-Hydroxylation of Tetralone-Derived β-Ketoesters: Asymmetric Synthesis of β- and γ-Substituted Tetralone Derivatives via Organocatalytic Oxidative Kinetic Resolution
  作者：Minami Odagi、Kota Furukori、Yoshiharu Yamamoto、Makoto Sato、Keisuke Iida、Masahiro Yamanaka、Kazuo Nagasawa

  DOI：10.1021/ja511149y

  日期：2015.2.11

  The mechanism of asymmetric a-hydroxylation of tetralone-derived beta-ketoesters with guanidine-bisurea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP) was examined by means of DFT calculations to understand the origin of the stereocontrol in the reaction. The identified transition-state model was utilized to design an enantioselective synthesis of beta- or gamma-substituted tetralones by catalytic oxidative kinetic resolution reaction of tetralone-derived beta-ketoesters. This kinetic resolution reaction proceeded with high selectivity, and selectivity factors (s value) of up to 99 were obtained. The potential utility of this oxidative kinetic resolution method for synthesis of natural products was confirmed by applying it to achieve an enantioselective synthesis of (+)-linoxepin (13) from beta-substituted tetralone rac-7 in only six steps.
• Selvaraj, S.; Ramakrishnan, P. S.; Arumugam, N., Recueil des Travaux Chimiques des Pays-Bas, 1989, vol. 108, # 1, p. 36 - 37
  作者：Selvaraj, S.、Ramakrishnan, P. S.、Arumugam, N.

  DOI：——

  日期：——