喹啉-2-羧酸丁酯 | 1025760-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 喹啉-2-羧酸丁酯
• 英文名称: butyl quinoline-2-carboxylate
• 英文别名: butyl quinaldate；quinoline-2-carboxylic acid butyl ester；n-Butyl quinaldate
• CAS: 1025760-23-9
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD24862823
• 分子量: 229.279
• InChiKey: LAXMGFMRJIKVCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  喹啉-2-羧酸丁酯 在 菲啶 、 diiodo(p-cymene)ruthenium(II) dimer 、 双(对硝基苯基)磷酸酯 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 60.0 ℃ 、3.45 MPa 条件下， 生成 butyl 1,2,3,4-tetrahydroquinoline-2-carboxylate
  参考文献：
  名称：

  2-官能化四氢喹啉的仿生还原对映选择性合成

  摘要：

  在转移催化剂简单的非手性磷酸存在下，利用手性和可再生的 NAD(P)H 模型 CYNAM 成功开发了 2-官能化喹啉的仿生不对称还原，提供了高达 99% ee 的手性 2-官能化四氢喹啉。使用该方法作为关键步骤，合成了一种含有 1,2,3,4-四氢喹啉基序的手性强效阿片类镇痛剂，总收率高。

  DOI：

  10.1021/acs.orglett.1c03430
• 作为产物：
  描述：

  喹哪啶酸 在 碘 、 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 5.67h， 生成 喹啉-2-羧酸丁酯
  参考文献：
  名称：

  Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids

  摘要：

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

  DOI：

  10.1021/jo302502r

文献信息

• Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group
  作者：Yuji Nakatani、Yuichiro Koizumi、Ryu Yamasaki、Shinichi Saito

  DOI：10.1021/ol800576w

  日期：2008.5.1

  The conversion of ketones to esters has been achieved through the use of Cu catalyst and tetrabutylammonium nitrite. This reaction involves the activation of the less activated C-C bond, and the alkyl group is removed as a leaving group. Various isopropyl ketones are found to be good substrates for this reaction.

  通过使用铜催化剂和亚硝酸四丁铵，已将酮转化为酯。该反应涉及活化程度较低的CC键的活化，并且烷基作为离去基团被除去。发现各种异丙基酮是该反应的良好底物。
• Transesterification for Synthesis of Carboxylates Using Aldehydes as Acyl Donors via C–H and C–O Bond Activations
  作者：Yong-Sheng Bao、Chao-Yue Chen、Zhi-Zhen Huang

  DOI：10.1021/jo3012573

  日期：2012.9.21

  A new type of transesterification between aryl, heteroaryl, alkyl N-heteroarene-2-carboxylates and various aldehydes by C–H and C–O bond activations has been developed for the synthesis of versatile carboxylates. A possible mechanism containing oxidative addition of acyl–O bond in parent ester and radical cleavage of sp2 C–H bond in aldehyde is proposed.

  已经开发了一种通过CH和C-O键活化在芳基，杂芳基，烷基N-杂芳基-2-羧酸酯和各种醛之间进行新型酯交换的方法，用于合成多种羧酸酯。提出了一种可能的机理，其中包括母体酯中酰基-O键的氧化加成和醛中sp 2 C-H键的自由基裂解。
• Copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols
  作者：Min Liu、Tieqiao Chen、Shuang-Feng Yin

  DOI：10.1039/c5cy02069g

  日期：——

  Efficient copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols has been developed. A variety of N-heteroaryl esters including those with functional groups are produced in good to excellent yields under the present reaction conditions.

  已经开发出N-杂芳基甲烷与醇的铜催化的好氧氧化酯化反应。在本反应条件下，以良好或优异的产率制备了各种N-杂芳基酯，包括具有官能团的N-杂芳基酯。
• Solid state structures of nonemitting complexes of cuprous iodide: (CuI(methylquinaldate))x (I), (CuI(isopropylquinaldate))2 (II) and (CuI(n-butylquinaldate))2 (III)
  作者：Jay A. Tompkins、Jana L. Maxwell、E.M. Holt

  DOI：10.1016/s0020-1693(00)88356-5

  日期：1987.2

  The three complexes exhibit tetrahedral copper coordination to two iodine atoms and the carbonyl oxygen and nitrogen atoms of a single quinaldate ester molecule, however, complex I shows a chain of alternating copper and iodine atoms whereas II and III crystallize with rhombohedra of alternating copper and iodine atoms. These three solid materials thus display similarity to known complexes of cuprous

  摘要碘化亚铜与奎宁酸的甲基，异丙基和正丁酯形成1：1：1配合物（Cu：I：配体）：（CuI（methylquinaldate））x（I），CuIC11H9NO2，a = 9.810（5） ，b = 15.486（14），c = 4.108（2）A，α= 81.32（6），β= 87.74（4），γ= 108.18（5）°，Dcalc = 2.148 g cm-3，Z = 2，三斜空间群P 1 R = 6.8％，观察到2044次反射；（CuI（异丙基喹啉））2（II），CuIC13H13NO2，a = 9.053（4），b = 22.554（10），c = 10.496（3）A，α= 52.37（3），β= 115.67（3），γ ＝ 153.48（2）°，Dcalc ＝ 1.876g cm-3，Z ＝ 2，三斜空间群P 1，对于2279个观察到的反射，R ＝ 4.7％。（CuI（正丁基正丁
• Alderweireldt, F. C.; Kemps, L.; Esmans, E. L., Heterocycles, 1984, vol. 21, # 2, p. 795
  作者：Alderweireldt, F. C.、Kemps, L.、Esmans, E. L.、Dommisse, R. A.、Lepoivre, J. A.

  DOI：——

  日期：——