1-naphthyl 2-phenylpropanoate | 190189-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthyl 2-phenylpropanoate
• 英文别名: Naphthalen-1-yl 2-phenylpropanoate
• CAS: 190189-36-7
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: DSGDKHAIMXZHBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-naphthyl 2-phenylpropanoate 在 NaY 作用下， 以 正己烷 为溶剂， 反应 2.0h， 生成 1-[2-(1-hydroxynaphthyl)]-2-phenyl-1-propanone
  参考文献：
  名称：

  沸石中 1-萘基苯基酰化物和二苄基酮光重排过程中碱金属离子控制的产物选择性

  摘要：

  比较了沸石中包含的 1-萘基苯基酰化物和二苄基酮的光化学行为。1-萘基苯基酰化物在溶液中产生八种光产物；在 NaY 中，它提供了一个单一的产品。选择性归因于沸石中存在的碱金属离子对初级自由基对的迁移率的限制。NaY 内二苄基酮的光化学表明笼自由基对中的系统间交叉可能受重碱金属离子的影响。在 B3LYP 水平计算的 Li+ 离子与客体 1-萘基苯乙酸酯和二苄基酮之间的配合物结构有助于理解沸石内观察到的产物选择性的起源。关键词：photo-Fries 反应，沸石，阳离子？ π 相互作用、自旋轨道耦合、重原子效应。

  DOI：

  10.1139/v03-041
• 作为产物：
  描述：

  2-Bromessigsaeure(1-naphthyl)ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-naphthyl 2-phenylpropanoate
  参考文献：
  名称：

  Cycloadditionen. 26. Einfluß von Substituenten in der allenischen ω-Position auf das Thermische Verhalten von Allencarbonsäurearylester

  摘要：

  The [(aryloxycarbonyl)methyl]triphenylphosphonium salts (1a and i), obtained by reaction of aryl bromoacetates with triphenylphophine, react with the acid chlorides 3 in the presence of two equivalents of triethylamine to give the phenyl- or the (1-naphthyl)-2,3-alkadienoates (4a-d and 4e-h), respectively, in the most cases accompanied by the aryl alkynoates 6 and 7 and/or with the naphthyl esters 8 of the used acids. Treatment of the [(aryloxycarbonyl)methyl] triphenylphosphonium salts (1a-i) with triethylamine furnishes the phosphoranes 2a-i, which are transformed by reaction with diphenylketene into the aryl 3,3-diphenyl-2,3-butadienoates (5). Heating of the derivatives 4a-d and 5a, bearing the unsubstituted phenyl nucleus in the ester moiety, leads to destruction, while heating of the naphthyl esters 4e-h and 5i - room temperature is sufficient in some cases - induces the IMDA-reaction to give the benzo-tricycles 9a-e. Heating of the 4,4-diphenyl-2,3-butadienoates (5b-h), bearing the alkylsubstituted phenyl ring within the ester component, induces radical dimerization to give the cylobutanes 10b-h, which represent the head to tail dimers.

  DOI：

  10.1002/prac.19973390142

文献信息

• Mediation of Photochemical Reactions of 1-Naphthyl Phenylacylates by Polyolefin Films. A ‘Radical Clock’ to Measure Rates of Radical-Pair Cage Recombinations in ‘Viscous Space’
  作者：Weiqiang Gu、Richard G. Weiss

  DOI：10.1016/s0040-4020(00)00512-3

  日期：2000.9

  generated upon irradiation of 1-naphthyl phenylacetate (1a) and 1-naphthyl 2-phenylpropanoate (1b) in three unstretched and stretched polyethylene films and isotactic and syndiotactic polypropylene films have been investigated. From dynamic fluorescence measurements, the primary locus of reactions by 1 is within amorphous regions of the films. The reaction cages afforded by these media inhibit escape of the

  研究了在三个未拉伸和拉伸的聚乙烯薄膜以及等规和间同规聚丙烯薄膜中，辐射1-萘基苯基乙酸酯（1a）和1-萘基2-苯基丙酸酯（1b）时产生的苯基酰基/ 1-萘氧基单线态自由基对的命运。从动态荧光测量中，主要反应位点为1在膜的无定形区域内。这些介质提供的反应笼抑制了自由基对的逸出，并介导了它们的重新定向运动，从而导致了光炸和相关产物的生成。从本质上讲，这些笼子起着坚固壁模板的作用。另外，描述了一种测量单线态自由基对的速率常数的方法。因此，来自基团对1（> 10 8  s -1）的2-苯基酰基-1-萘酚的速率常数（导致酮前体））是4异构体速率常数的> 6倍。膜拉伸增加了这种选择性，但是笼内自由基对的重组速率与宏观聚合物，诸如结晶度和支链频率等性质之间没有明显的相关性。相比之下，2-苄基-1-萘酚的（酮前体）的形成（由苯酰基脱羰基化后的笼内重组）比4-苄基-1-萘酚的形成要慢。
• 2-Phenylpropionic acid esters, method for optical resolution thereof and optically active substance thereof
  申请人：NISSAN CHEMICAL INDUSTRIES LTD.

  公开号：EP0179487A1

  公开（公告）日：1986-04-30

  2-Phenylpropionic acid ester of Formula (l): wherein R represents p-nitrophenyl group, β-naphthyl group or 2-(β-naphthyl)ethyl group. Optical resolution of the above is carried out by preferential crystallization by seeding either one of the optical isomers into a super-saturated solution of a racemic modification thereof or a mixture of the optical isomers thereof. The efficiency of the optical resolution can be increased by optional addition of a racemizing agent comprising a strongly basic amine or an alcoholate.

  式（l）的 2-苯基丙酸酯： 其中 R 代表对硝基苯基、β-萘基或 2-（β-萘基）乙基。 上述物质的光学分辨是通过将其中一种光学异构体加入其外消旋体或其光学异构体混合物的过饱和溶液中进行优先结晶来实现的。可选择添加由强碱性胺或醇酸酯组成的消旋化剂，从而提高光学解析的效率。
• Photo-Fries Reactions of 1-Naphthyl Esters in Cation-Exchanged Zeolite Y and Polyethylene Media
  作者：Weiqiang Gu、Manoj Warrier、V. Ramamurthy、Richard G. Weiss

  DOI：10.1021/ja990818o

  日期：1999.10.1
• Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates
  作者：Smriti Koodanjeri、Ajit R Pradhan、Lakshmi S Kaanumalle、V Ramamurthy

  DOI：10.1016/s0040-4039(03)00422-2

  日期：2003.4

  1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via beta-cleavage process. However, excitation of these molecules as included in gamma-cyclodextrin results in a single product (>95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Alkali metal ion controlled product selectivity during photorearrangements of 1-naphthyl phenyl acylates and dibenzyl ketones within zeolites
  作者：M Warrier、Lakshmi S Kaanumalle、V Ramamurthy

  DOI：10.1139/v03-041

  日期：2003.6.1

  acylates and dibenzyl ketones included in zeolites have been compared. 1-Naphthyl phenyl acylates while in solution produce eight photoproducts; within NaY it gives a single product. The selectivity is attributed to the restriction brought on the mobility of the primary radical pair by the alkali metal ions present in zeolites. Photochemistry of dibenzyl ketones within NaY reveals that the intersystem crossing

  比较了沸石中包含的 1-萘基苯基酰化物和二苄基酮的光化学行为。1-萘基苯基酰化物在溶液中产生八种光产物；在 NaY 中，它提供了一个单一的产品。选择性归因于沸石中存在的碱金属离子对初级自由基对的迁移率的限制。NaY 内二苄基酮的光化学表明笼自由基对中的系统间交叉可能受重碱金属离子的影响。在 B3LYP 水平计算的 Li+ 离子与客体 1-萘基苯乙酸酯和二苄基酮之间的配合物结构有助于理解沸石内观察到的产物选择性的起源。关键词：photo-Fries 反应，沸石，阳离子？ π 相互作用、自旋轨道耦合、重原子效应。