methyl 4-bromo-3-methoxy-2-naphthoate | 1211483-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-bromo-3-methoxy-2-naphthoate
• 英文别名: methyl 4-bromo-3-methoxynaphthalene-2-carboxylate
• CAS: 1211483-19-0
• 化学式: C₁₃H₁₁BrO₃
• 分子量: 295.133
• InChiKey: AOXKFKOSRQQTPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  methyl 4-bromo-3-methoxy-2-naphthoate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 1,1,3,3-四甲基二硅氧烷 、 palladium diacetate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 methyl 4-phenyl-2-naphthoate
  参考文献：
  名称：

  Ni-Catalyzed Reduction of Inert C−O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups

  摘要：

  An efficient Ni-catalyzed protocol for the reductive cleavage of inert C-O bonds has been developed. The method is characterized by its simplicity and wide scope, thereby allowing the use of aryl ethers as easily removable directing groups in organic synthesis.

  DOI：

  10.1021/ja106943q
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成 methyl 4-bromo-3-methoxy-2-naphthoate
  参考文献：
  名称：

  通过 Atroposelective Miyaura Borylation 构建轴向手性芳基硼

  摘要：

  与发达的中心手性硼化学相比，C-B 轴向手性化学仍然难以捉摸和具有挑战性。在此，我们报告了第一次使用不对称二硼试剂对溴芳烃进行阻转选择性 Miyaura 硼酸化，用于直接催化合成旋光阻转异构芳基硼。该反应具有广泛的底物范围，可产生高产率和良好对映选择性的轴向手性芳基硼。

  DOI：

  10.1021/jacs.1c04345

文献信息

• Pd-Catalyzed 1,4-Carboamination of Bicyclic Bromoarenes with Diazo Compounds and Amines
  作者：Qikun Wu、Kei Muto、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.2c01233

  日期：2022.6.17

  A palladium-catalyzed 1,4-carboamination of bromoarenes with diazo compounds and amines was developed. This reaction proceeds through a palladium-carbene that then generates a π-benzylpalladium intermediate, forming ipso C–C and para C–N bonds on bromoarenes in a regioselective manner. The successful application of this transformation to the rapid synthesis of an antitumor agent demonstrates its synthetic

  开发了钯催化的溴代芳烃与重氮化合物和胺的 1,4-羰基化反应。该反应通过钯-卡宾进行，然后生成 π-苄基钯中间体，以区域选择性的方式在溴芳烃上形成同样的 C-C 和对 C- N键。这种转化成功地应用于抗肿瘤药物的快速合成证明了它的合成效用。
• Dearomatization of (Hetero)arenes through Photodriven Interplay between Polysulfide Anions and Formate**
  作者：Eugene Yew Kun Tan、Amirah S. Mat Lani、Wayne Sow、Yuliang Liu、Haoyu Li、Shunsuke Chiba

  DOI：10.1002/anie.202309764

  日期：2023.10.2

  protocol was developed for the dearomatization of substituted naphthalenes, indoles, and related heteroaromatic compounds through a radical-polar crossover mechanism induced by single-electron transfer from photoexcited polysulfide anions in the presence of methanol. The catalytic turnover is maintained by hydrogen-atom transfer between polysulfide radical anions and formate.

  开发了一种光催化方案，通过在甲醇存在下光激发多硫化物阴离子的单电子转移诱导的自由基-极性交叉机制，用于取代萘、吲哚和相关杂芳族化合物的脱芳构化。催化转化通过多硫化物自由基阴离子和甲酸盐之间的氢原子转移来维持。
• Enantioselective C–H Arylation for Axially Chiral Heterobiaryls
  作者：Ziyue Liu、Ben Gao、Konstantin Chernichenko、He Yang、Sébastien Lemaire、Wenjun Tang

  DOI：10.1021/acs.orglett.3c02478

  日期：2023.9.29

  palladium-catalyzed C–H arylation of functionalized pyrazoles/triazoles/imidazoles is developed, affording a variety of axially chiral ortho-nitro/formyl-substituted heterobiaryls with excellent enantioselectivities and good yields. The method features a deuterated P-chiral phosphorus ligand CD3-AntPhos, a broad substrate scope of functionalized heterobiaryls, mild reaction conditions, and low palladium loadings

  开发了功能化吡唑/三唑/咪唑的对映选择性钯催化C-H芳基化，提供了多种轴向手性邻硝基/甲酰基取代的杂联芳基化合物，具有优异的对映选择性和良好的产率。该方法具有氘代 P-手性磷配体 CD 3 -AntPhos、功能化杂联芳基的广泛底物范围、温和的反应条件和低钯负载量。
• Ni-Catalyzed Reduction of Inert C−O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups
  作者：Paula Álvarez-Bercedo、Ruben Martin

  DOI：10.1021/ja106943q

  日期：2010.12.15

  An efficient Ni-catalyzed protocol for the reductive cleavage of inert C-O bonds has been developed. The method is characterized by its simplicity and wide scope, thereby allowing the use of aryl ethers as easily removable directing groups in organic synthesis.
• Construction of Axially Chiral Arylborons via Atroposelective Miyaura Borylation
  作者：Kai Yang、Yanfei Mao、Jie Xu、Hao Wang、Yong He、Wangyang Li、Qiuling Song

  DOI：10.1021/jacs.1c04345

  日期：2021.7.14

  well-developed centrally chiral boron chemistry, C–B axially chiral chemistry remains elusive and challenging. Herein we report the first atroposelective Miyaura borylation of bromoarenes with unsymmetrical diboron reagents for the direct catalytic synthesis of optically active atropisomeric arylborons. This reaction features broad substrate scope and produces axially chiral arylborons with high yields

  与发达的中心手性硼化学相比，C-B 轴向手性化学仍然难以捉摸和具有挑战性。在此，我们报告了第一次使用不对称二硼试剂对溴芳烃进行阻转选择性 Miyaura 硼酸化，用于直接催化合成旋光阻转异构芳基硼。该反应具有广泛的底物范围，可产生高产率和良好对映选择性的轴向手性芳基硼。