2,2-二苄基四氢萘-1-酮 | 6340-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2,2-二苄基四氢萘-1-酮
• 英文名称: 2,2-dibenzyl-1-tetralone
• 英文别名: 2,2-dibenzyl-α-tetralone；2,2-dibenzyl-3,4-dihydronaphthalen-1(2H)-one；2,2-dibenzyl-3,4-dihydronaphthalen-1-one
• CAS: 6340-82-5
• 化学式: C₂₄H₂₂O
• 分子量: 326.438
• InChiKey: VYCYIUPAMOTMKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2-benzyl-1-tetralone 、 溴甲苯 在 六甲基磷酰三胺 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.33h， 以42%的产率得到2,2-二苄基四氢萘-1-酮
  参考文献：
  名称：

  Rate Enhancement with High Ratio of the Monoalkylated Product to the Dialkylated Product in the Alkylation of the Lithium Enolate of 1-Tetralone with Reactive Alkyl Halides.

  摘要：

  研究了 1-四氢萘酮的锂烯醇盐与活性烷基卤化物在没有和有 3 等量各种锂配体的情况下发生的反应。结果表明，在存在四价胺（1, 1, 4, 7, 10, 10-六甲基三乙烯四胺）的情况下，反应速率大大提高，而且在较短的反应时间内，单烷基化产物与二烷基化产物的比例也会增加。

  DOI：

  10.1248/cpb.48.1529

文献信息

• N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions
  作者：Marcus Blümel、Reece D. Crocker、Jason B. Harper、Dieter Enders、Thanh V. Nguyen

  DOI：10.1039/c6cc03771b

  日期：——

  N-Heterocyclic Olefins (NHOs) have very recently emerged as efficient promoters for several chemical reactions due to their strong Bronsted/Lewis basicities. Here we report the novel application of NHOs as efficient...

  N-杂环烯烃（NHOs）由于其强大的Bronsted / Lewis基础性，最近已成为多种化学反应的有效促进剂。在这里，我们将NHO的新颖应用报告为高效...
• 1,1,4,7,10-10-Hexamethyltriethylenetetramine: a reagent to enhance the rate of alkylation reaction of the lithium enolate of 1-tetralone with alkyl halides
  作者：Mariko Goto、Koh-ichi Akimoto、Kazumasa Aoki、Mitsuru Shindo、Kenji Koga

  DOI：10.1016/s0040-4039(99)01721-9

  日期：1999.11

  The rate of the reaction of the lithium enolate of 1-tetralone with alkyl halides was enhanced greatly in the presence of 3 equivalents of 1,1,4,7,10,10-hexamethyltriethylenetramine. The ratio of the monoalkylated product to the dialkylated product was found to have increased under a shorter reaction time.

  在3当量的1,1,4,7,10,10-六甲基三亚乙基三胺存在下，1-四氢萘酮的烯醇锂与烷基卤的反应速率大大提高。发现单烷基化产物与二烷基化产物的比例在较短的反应时间下增加。
• Why Is Alkylation of an Enolate Accompanied by So Much Polyalkylation?
  作者：Andrew Streitwieser、Yeong-Joon Kim、Daniel Ze-Rong Wang

  DOI：10.1021/ol0162872

  日期：2001.8.9

  text] The lithium enolate 1-Li of 6-phenyl-alpha-tetralone forms a monomer-tetramer equilibrium in THF at 25 degrees C with K(1,4) = 4.7E+10 M(-3). The lithium enolate 2-Li, however, forms a monomer-dimer equilibrium with K(1,2) = 3800 M(-1). In both cases reaction with benzyl bromide is dominantly with the monomer. The results support an earlier conjecture of House that alkylation of an enolate is frequently

  [反应：见正文] 6-苯基-α-四氢萘酮的烯醇锂1-Li在25°C下的THF中以K（1,4）= 4.7E + 10 M（-3）形成单体-四聚物平衡。然而，烯醇锂2-Li形成具有K（1,2）= 3800 M（-1）的单体-二聚体平衡。在两种情况下，与苄基溴的反应主要与单体反应。结果支持了豪斯的一个早期推测，即烯醇化物的烷基化经常伴随着广泛的多烷基化，因为取代度较低的烯醇化物更聚集。
• On the π-π interaction in the benzylation of ketones
  作者：Enrique Díez-Barra、Sonia Merino、Prado Sánchez-Verdú、José Torres

  DOI：10.1016/s0040-4020(97)00724-2

  日期：1997.8

  The benzylation of a set of nine ketones provides enough information to establish how the ketone structure affects the existence of a pi-pi interaction. The presence of a phenyl moiety starting from the alpha-carbon atom and flexibility in cyclic ketones are structural features required for effective interactions. The pi-pi interaction is controlled by a polar-pi effect. Stronger interaction is achieved when slight electronwithdrawing groups are present in both pi-system. This results is explained by the predominance of the sigma-pi shells attractive interaction in an edge-to-face geometry. (C) 1997 Elsevier Science Ltd.
• Rate Enhancement with High Ratio of the Monoalkylated Product to the Dialkylated Product in the Alkylation of the Lithium Enolate of 1-Tetralone with Reactive Alkyl Halides.
  作者：Mariko GOTO、Koh-ichi AKIMOTO、Kazumasa AOKI、Mitsuru SHINDO、Kenji KOGA

  DOI：10.1248/cpb.48.1529

  日期：——

  The reactions of the lithium enolate of 1-tetralone with reactive alkyl halides were examined in the absence and in the presence of 3 eq of various ligands for the lithium. It is shown that the rates of the reactions are enhanced greatly in the presence a tetradentate amine (1, 1, 4, 7, 10, 10-hexamethyltriethylenetetramine), and the ratio of the monoalkylated product to the dialkylated product is increased under shorter reaction times.

  研究了 1-四氢萘酮的锂烯醇盐与活性烷基卤化物在没有和有 3 等量各种锂配体的情况下发生的反应。结果表明，在存在四价胺（1, 1, 4, 7, 10, 10-六甲基三乙烯四胺）的情况下，反应速率大大提高，而且在较短的反应时间内，单烷基化产物与二烷基化产物的比例也会增加。