5-Ethyl-1-naphthoesaeure | 201654-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Ethyl-1-naphthoesaeure
• 英文别名: 5-Ethyl-1-naphthoic Acid；5-ethylnaphthalene-1-carboxylic acid
• CAS: 201654-84-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: JISXLGRROBKXCT-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  386.8±11.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Ethyl-1-naphthoesaeure 、 magnesium,diethyl propanedioate,ethanolate 生成 1-Acetyl-5-ethylnaphthalin
  参考文献：
  名称：

  The Substituent Effect. XI. Solvolysis of 5-, 6-, and 7-Substituted 1-(1-Naphthylethyl) Chlorides

  摘要：

  制备了十四个5-、6-和7-取代的1-(1-萘乙基)氯化物，并在45°C下，80%（体积/体积）的乙酸水溶液中测定了其溶剂分解速率。基于方程logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+)，处理了在相应位置上的−R取代基的影响。诱导效应的位置依赖性由Cij(=ρi⁄ρi,4α)给出；C3α=1.37，C4α=1.00，C5α=0.75，C6α=0.57，C7α=0.72。Cij值似乎与Dewar的简化场函数1/rij相关。由比率ρπ+⁄ρi,4α=qr·ij+给出的π电子效应的位置依赖性与从MO指数（如Forsyth的Δqij(ArCH2+参数）的预测一致。同样的处理也应用于其他三种萘的反应性：脱氢、α-萘甲酸的pKa和萘甲基铵离子的pKa。在这些反应中，线性ρi–ρi关系成立，表明诱导传递的反应独立方案。qr·ij+值在共轭位置随反应变化，但在非共轭位置不随反应变化。结果在与相关处理的比较中进行了讨论。

  DOI：

  10.1246/bcsj.48.3356
• 作为产物：
  描述：

  5-Methyl-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid 在 palladium on activated charcoal 作用下， 以66%的产率得到5-Ethyl-1-naphthoesaeure
  参考文献：
  名称：

  一个不寻常的AlCl 3催化的芳香环化反应：四氢萘甲酸的新型合成†

  摘要：

  描述了不寻常的AlCl 3催化的芳族环化反应。这用于开发由2-乙烯基苯甲酸（3a–d）合成5,6,7,8-四氢-5-烷基-1-萘甲酸（1a –d）的新方法。©1997 Elsevier ScienceLtd。保留所有权利。

  DOI：

  10.1016/s0040-4039(97)10462-2

文献信息

• Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of Trialkyl- boranes with Aryl Bromides in the Presence of Unmasked Acidic or Basic Functions and Base-Labile Protections under Mild Non-Aqueous Conditions
  作者：Bing Wang、Hui-Xia Sun、Zhi-Hua Sun、Guo-Qiang Lin

  DOI：10.1002/adsc.200800630

  日期：2009.2

  Abstractmagnified imageAn efficient and chemoselective palladium‐catalyzed direct B‐alkyl Suzuki–Miyaura cross‐coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non‐aqueous conditions are compatible with aldehydes, ketones, nitriles, chloro substitution as well as base‐labile phenolic Piv and TBS protecting groups. The anhydrous conditions were found to be advantageous for aryl bromide substrates. A potent CEPT inhibitor was efficiently synthesised using this protocol.
• B-Alkyl Suzuki–Miyaura cross-coupling of tri-n-alkylboranes with arylbromides bearing acidic functions under mild non-aqueous conditions
  作者：Hui-Xia Sun、Zhi-Hua Sun、Bing Wang

  DOI：10.1016/j.tetlet.2009.01.090

  日期：2009.4

  An efficient and chemoselective Pd-catalyzed B-alkyl Suzuki-Miyaura cross-coupling of tri-n-alkylboranes with arylbromides possessing acidic functions is described. This protocol features the relatively weak base CS2CO3 and mild non-aqueous conditions. Aldehydes, ketones, nitriles, and chloro substitution are all tolerated. (C) 2009 Elsevier Ltd. All rights reserved.
• The Substituent Effect. XI. Solvolysis of 5-, 6-, and 7-Substituted 1-(1-Naphthylethyl) Chlorides
  作者：Yuho Tsuno、Masami Sawada、Takahiro Fujii、Yoshihiko Tairaka、Yasuhide Yukawa

  DOI：10.1246/bcsj.48.3356

  日期：1975.11

  Fourteen 5-, 6-, and 7-substituted 1-(1-naphthylethyl) chlorides were prepared and the solvolysis rates were determined in 80% (v/v) aqueous acetone at 45 °C. The effects of −R substituents at respective positions were treated on the basis of the equation, logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+). The position dependency of the inductive effect was given by Cij(=ρi⁄ρi,4α); C3α=1.37, C4α=1.00, C5α=0.75, C6α=0.57, and C7α=0.72. The Cij values appear to be correlated with Dewar’s simplified field function 1/rij. The position dependency of Pi-electronic effect given by the ratio ρπ+⁄ρi,4α=qr·ij+ was consistent with the prediction from the MO indices, such as Forsyth’s Δqij(ArCH2+ parameters. The same treatment was applied also to three other naphthalene reactivities, detritiation, pKa of α-naphthoic acids and pKa of naphthylammonium ions. The linear ρi–ρi relation holds among these reactions, suggesting a reaction-independent scheme of the inductive transmission. The qr·ij+ values vary at conjugate positions with reaction but not at non-conjugate positions irrespective of reactions. The results are discussed in comparison with those of relevant treatments.

  制备了十四个5-、6-和7-取代的1-(1-萘乙基)氯化物，并在45°C下，80%（体积/体积）的乙酸水溶液中测定了其溶剂分解速率。基于方程logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+)，处理了在相应位置上的−R取代基的影响。诱导效应的位置依赖性由Cij(=ρi⁄ρi,4α)给出；C3α=1.37，C4α=1.00，C5α=0.75，C6α=0.57，C7α=0.72。Cij值似乎与Dewar的简化场函数1/rij相关。由比率ρπ+⁄ρi,4α=qr·ij+给出的π电子效应的位置依赖性与从MO指数（如Forsyth的Δqij(ArCH2+参数）的预测一致。同样的处理也应用于其他三种萘的反应性：脱氢、α-萘甲酸的pKa和萘甲基铵离子的pKa。在这些反应中，线性ρi–ρi关系成立，表明诱导传递的反应独立方案。qr·ij+值在共轭位置随反应变化，但在非共轭位置不随反应变化。结果在与相关处理的比较中进行了讨论。
• An Unusual AlCl3 Catalysed Aromatic Cyclisation Reaction : Novel Synthesis of Tetrahydronaphthoic Acids
  作者：Raghao S Mali、Milind D Sindkhedkar、Prakash G Jagtap

  DOI：10.1016/s0040-4039(97)10462-2

  日期：1998.1

  An unusual AlCl3 catalysed aromatic cyclisation reaction is described. This is used to develop a novel synthesis of 5,6,7,8-tetrahydro-5-alkyl-1-naphthoic acids (1a–d) from 2-vinylbenzoic acids (3a–d). © 1997 Elsevier Science Ltd. All rights reserved.

  描述了不寻常的AlCl 3催化的芳族环化反应。这用于开发由2-乙烯基苯甲酸（3a–d）合成5,6,7,8-四氢-5-烷基-1-萘甲酸（1a –d）的新方法。©1997 Elsevier ScienceLtd。保留所有权利。