3,4-dihydronaphthalen-1-yl acetate | 19455-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydronaphthalen-1-yl acetate
• 英文别名: 1,2-dihydro-4-naphthyl acetate；tetralone enol acetate；3,4-dihydro-1-naphthyl acetate；1-acetoxy-3,4-dihydronaphthalene；4-acetoxy-1,2-dihydronaphthalene；3,4-dihydronaphth-1-yl acetate
• CAS: 19455-84-6
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: GBRZVFKBTFSDHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-dihydronaphthalen-1-yl acetate 在 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.17h， 生成 2-hydroxy-1-tetralone
  参考文献：
  名称：

  Synthesis of Racemic and Enantiomerically Enriched a-Oxyfunctionalized Benzocyclanones and Chromanones by Dimethyldioxirane and Dimethyldioxirane/Mn(III) salen System

  摘要：

  Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic alpha-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position alpha in the whole series.

  DOI：

  10.1007/s00706-004-0159-9
• 作为产物：
  描述：

  乙酸异丙烯酯 、 3,4-二氢-1(2H)-萘酮 在 对甲苯磺酸 作用下， 反应 18.0h， 生成 3,4-dihydronaphthalen-1-yl acetate
  参考文献：
  名称：

  一种将 α-四氢萘酮转化为芳基乙酸酯的简便方法

  摘要：

  摘要 用乙酸异丙烯酯和对甲苯磺酸通过 α-四氢萘酮轻松合成乙酸芳基酯，然后用空气或 DDQ 在一锅法中脱氢。

  DOI：

  10.1080/00397919108019787

文献信息

• A Method for the Net Contra-thermodynamic Isomerization of Cyclic Trisubstituted Alkenes
  作者：Raphaël F. Guignard、Laurent Petit、Samir Z. Zard

  DOI：10.1021/ol4018744

  日期：2013.8.16

  A simple sequence for the net contra-thermodynamic isomerization of cyclic trisubstituted alkenes is reported consisting of a radical addition of p-chlorothiophenol, followed by oxidation to the sulfoxide and thermal syn-elimination to give the least substituted isomeric cycloalkene.

  为环状三取代烯烃的净禁忌热力学异构化的简单序列报道由自由基加成的p -chlorothiophenol，随后氧化成亚砜和热合成β-消除，得到至少取代的同分异构的环烯烃。
• Reductive Coupling between C–N and C–O Electrophiles
  作者：Rong-De He、Chun-Ling Li、Qiu-Quan Pan、Peng Guo、Xue-Yuan Liu、Xing-Zhong Shu

  DOI：10.1021/jacs.9b05224

  日期：2019.8.14

  The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been

  交叉亲电反应是 CC 键形成的一个有前景的策略。最近的研究主要集中在与有机卤化物的反应上。在这里，我们报告了 CN 和 CO 亲电试剂之间的偶联反应，证明了通过 CN 和 CO 裂解构建 CC 键的可能性。已经研究了苄基/芳基铵盐和乙烯基/芳基 CO 亲电试剂之间的几种反应。初步机理研究表明，苄基铵是通过自由基机制活化的。
• An efficient α-hydroxylation of carbonyls using the HOF•CH3CN complex
  作者：Sharon Dayan、Yifat Bareket、Shlomo Rozen

  DOI：10.1016/s0040-4020(98)01173-9

  日期：1999.3

  The complex HOF•CH3CN, made directly from fluorine and aqueous acetonitrile, was used for α-hydroxylation of various ketones, esters and acids via their trimethyl silyl enol ethers. The reaction is usually complete in a few minutes at room temperature or below and has high yields.

  直接由氟和乙腈水溶液制得的HOF•CH 3 CN络合物通过三甲基甲硅烷基烯醇醚用于各种酮，酯和酸的α-羟基化反应。该反应通常在室温或低于室温的几分钟内完成，并且收率高。
• α-Iodination of Ketones and Enol Acetates with Poly[styrene-<i>co</i>-(4-vinylpyridinium dichloroiodate(1–))]
  作者：Boris \u{S}ket、Pavel Zupet、Marko Zupan、Darko Dolenc

  DOI：10.1246/bcsj.62.3406

  日期：1989.10

  Crosslinked poly[styrene-co(4-vinylpyridinium dichloroiodate(1–))] can be used as a very efficient polymeric reagent for α-iodination of ketones, diketones, and corresponding enol acetates.

  交联的聚[苯乙烯-共-(4-乙烯基吡啶二氯碘化物(1–))]可用作非常高效的聚合物试剂，用于酮、二酮及其相应烯醇乙酸酯的α-碘化。
• Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
  作者：Dominik Gärtner、André Luiz Stein、Sabine Grupe、Johannes Arp、Axel Jacobi von Wangelin

  DOI：10.1002/anie.201504524

  日期：2015.9.1

  unreactive in cross‐coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross‐couplings because the strong CO bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron‐catalyzed cross‐coupling of diverse alkenyl

  稳定的CO键通常在交叉偶联反应中没有反应性，而交叉偶联反应通常使用更多的亲电子卤化物或活化的酯（三氟甲磺酸酯，甲苯磺酸酯）。乙酸盐价格便宜，易于获得亲电试剂，但由于其强大的CO键和极高的参与不希望的乙酰化和去质子化的能力，因此并未用于交叉偶联中。本文报道了多种乙酸烯基酯的选择性铁催化交叉偶联，它在温和的反应条件下（0°C，2 h）与不含配体的催化剂（1-2 mol％）一起运行。