3-bromobutyl 4-methoxybenzoate | 1282036-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-bromobutyl 4-methoxybenzoate
• 英文别名: 3-Bromobutyl 4-methoxybenzoate
• CAS: 1282036-54-7
• 化学式: C₁₂H₁₅BrO₃
• 分子量: 287.153
• InChiKey: YFFKHEOEXBIQOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromobutyl 4-methoxybenzoate 在 [Cu(2,9-dimethyl-1,10-phenanthroline)2]*-[HF₂]- 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以74%的产率得到3-Fluorobutyl 4-methoxybenzoate
  参考文献：
  名称：

  Efficient S_N2 Fluorination of Primary and Secondary Alkyl Bromides by Copper(I) Fluoride Complexes

  摘要：

  Copper(I) fluoride complexes ligated by phenanthroline derivatives have been synthesized and structurally characterized by X-ray crystallography. These complexes adopt as either ionic or neutral forms in the solid state, depending on the steric bulkiness of the substituent groups on the phenanthroline ligands. These complexes react with primary and secondary alkyl bromides to produce the corresponding alkyl fluorides in modest to good yields. This new method is compatible with a variety of important functional groups such as ether, thioether, amide, nitrile, methoxyl, hydroxyl, ketone, ester, and heterocycle moieties.

  DOI：

  10.1021/om4008967
• 作为产物：
  描述：

  3-hydroxybutyl-4-methoxy benzoate 在 咪唑 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 3-bromobutyl 4-methoxybenzoate
  参考文献：
  名称：

  镍催化的未活化烷基卤化物的还原交叉偶联

  摘要：

  已成功开发了镍催化的还原方法，用于两个未活化的烷基卤的交叉偶联。该反应对于伯卤和仲卤有效地起作用，其中至少一种是溴。温和的反应条件允许出色的官能团耐受性，并以中等至极好的收率提供C（sp 3）-C（sp 3）偶联产物。

  DOI：

  10.1021/ol200617f

文献信息

• Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated­ Alkyl Halides
  作者：Qun Qian、Kunhua Lin、Hegui Gong、Jun Gu、Canbin Qiu、Wenbin Lu

  DOI：10.1055/s-0036-1588132

  日期：——

  ligand for the reductive vinylation of unactivated secondary alkyl halides under Ni-catalyzed conditions has been developed. Both alkyl- and aryl-substituted vinyl bromides are suitable, in which alkyl-decorated α-alkenyl bromides resulted in the α-products in good results. The use of pyridine as the sole ligand for the reductive vinylation of unactivated secondary alkyl halides under Ni-catalyzed conditions

  ‡这些作者的贡献相等 抽象的 已经开发了使用吡啶作为唯一的配体，用于在镍催化的条件下将未活化的仲烷基卤化物还原乙烯基化。烷基取代的和芳基取代的乙烯基溴化物都是合适的，其中烷基修饰的α-烯基溴化物导致α产物的结果良好。 已经开发了使用吡啶作为唯一的配体，用于在镍催化的条件下将未活化的仲烷基卤化物还原乙烯基化。烷基取代的和芳基取代的乙烯基溴化物都是合适的，其中烷基修饰的α-烯基溴化物导致α产物的结果良好。
• Nickel-Catalyzed Reductive Alkylation of Halogenated Pyridines with Secondary Alkyl Bromides
  作者：Huiyan Liu、Zhuye Liang、Qun Qian、Kunhua Lin

  DOI：10.1080/00397911.2014.924141

  日期：2014.10.18

  Abstract This article highlights Ni-catalyzed cross-electrophile coupling of halogenated pyridines with secondary alkyl bromides using zinc as the terminal reductant. With this protocol, we have successfully achieved different alkyl-substituted pyridines in moderate to excellent yields. GRAPHICAL ABSTRACT

  摘要 本文重点介绍了使用锌作为末端还原剂的卤代吡啶与仲烷基溴的 Ni 催化交叉亲电偶联。通过该协议，我们成功地以中等至优异的产率实现了不同的烷基取代吡啶。图形概要
• Alkyl–aryl ketone synthesis via nickel-catalyzed reductive coupling of alkyl halides with aryl acids and anhydrides
  作者：Xiao Jia、Xinghua Zhang、Qun Qian、Hegui Gong

  DOI：10.1039/c5cc03113c

  日期：——

  The present work disclosed a much improved method for the construction of alkyl‒aryl ketones by direct coupling of unactivated alkyl bromides with 1.5 equiv of acids. In addition, the synthesis...

  本工作公开了一种通过将未活化的烷基溴化物与1.5当量的酸直接偶联来制备烷基‒芳基酮的改进方法。另外，合成...
• Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis(pinacolato)diboron as reductant
  作者：Hailiang Xu、Chenglong Zhao、Qun Qian、Wei Deng、Hegui Gong

  DOI：10.1039/c3sc51098k

  日期：——

  The use of bis(pinacolato)diboron as the terminal reductant allows the efficient Ni-catalyzed coupling of unactivated secondary and primary alkyl halides, generating the C(sp3)–C(sp3) coupling products in good yields. The mild catalytic conditions display excellent functional group tolerance, and good chemoselectivities which require only 1.5 equiv. of primary bromides for the coupling with secondary bromides. Preliminary mechanistic studies suggest that an in situ organoborane/Suzuki process is not likely. It was identified that the base and ligand have more profound impact on selecting this reductive coupling pathway. The good chemoselectivity appears to be evoked by the formation of Ni–Bpin catalytic intermediates, which demands matched sizes and reactivities of the alkyl halide coupling partners for optimal coupling efficiency.

  使用双（匹卡洛酸酯）二硼作为末端还原剂，可以高效催化非活化的次级和一级卤烃进行镍催化偶联反应，生成良产率的C(sp3)–C(sp3)偶联产物。这种温和的催化条件表现出优异的官能团耐受性，以及良好的化学选择性，仅需1.5当量的一级溴化物与次级溴化物进行偶联。初步的机理研究表明，体内有机硼/铃木反应的可能性不大。研究发现，碱和配体对选择这一还原偶联路径有更深远的影响。良好的化学选择性似乎是由于Ni–Bpin催化中间体的形成，这要求卤烃偶联伙伴之间的尺寸和反应性匹配，以实现最佳偶联效率。
• Dehalogenative deuteration of alkyl and aryl bromides by thiyl radical catalysis under visible-light irradiation
  作者：Jiin Lee、Sunggi Lee

  DOI：10.1039/d4cc00474d

  日期：——

  Herein, we report a mild and practical method for the deuteration of alkyl and aryl bromides by a thiyl radical catalyst and halogen-atom transfer (XAT) using disulfides and silanes under visible-light irradiation. In this study, various organic bromides such as 1°, 2°, and 3°-alkyl bromides and aryl bromides were converted to deuterated products in good to excellent yields and D-incorporation.

  在此，我们报告了一种温和实用的方法，通过硫基自由基催化剂对烷基溴和芳基溴进行氘化，并在可见光照射下使用二硫化物和硅烷进行卤素原子转移（XAT）。在这项研究中，各种有机溴化物（例如 1°、2° 和 3°-烷基溴和芳基溴）被转化为氘代产品，产率和 D 结合率良好至优异。