2-(chloromethyl)-2,1-borazaronaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(chloromethyl)-2,1-borazaronaphthalene
• 英文别名: 2-(chloromethyl)-1H-1,2-benzazaborinine
• 化学式: C₉H₉BClN
• 分子量: 177.441
• InChiKey: WCRHQFUUOUSAIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(chloromethyl)-2,1-borazaronaphthalene 在 sodium azide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以85%的产率得到2-(azidomethyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene

  摘要：

  One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This BN isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.

  DOI：

  10.1021/ol502708z
• 作为产物：
  描述：

  potassium (chloromethyl)trifluoroborate 、 2-氨基苯乙烯 在 四氯化硅 、 三乙胺 作用下， 反应 18.0h， 生成 2-(chloromethyl)-2,1-borazaronaphthalene
  参考文献：
  名称：

  Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene

  摘要：

  One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This BN isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.

  DOI：

  10.1021/ol502708z

文献信息

• Accessing 2-(Hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplings of 2-(Chloromethyl)-2,1-borazaronaphthalenes
  作者：Gary A. Molander、Javad Amani、Steven R. Wisniewski

  DOI：10.1021/ol5030508

  日期：2014.11.21

  1-borazaronaphthalene has provided an opportunity to expand dramatically the functionalization of the azaborines. This azaborinyl building block can serve as the electrophile in palladium-catalyzed cross-coupling reactions to form sp3–sp and sp3–sp2 bonds. The cross-coupling reactions of 2-(chloromethyl)-2,1-borazaronaphthalene with potassium (hetero)aryl- and alkenyltrifluoroborates as well as terminal alkynes provides

  2-(氯甲基)-2,1-硼氮杂萘的合成为大幅扩展氮杂硼烷的功能化提供了机会。这种氮杂硼烷基结构单元可在钯催化的交叉偶联反应中用作亲电子试剂，以形成 sp 3 -sp 和 sp 3 -sp 2键。2-(氯甲基)-2,1-硼杂萘与（杂）芳基-和烯基三氟硼酸钾以及末端炔烃的交叉偶联反应提供了获得各种新型氮杂硼烷的途径，从而可以制备假苄基取代的氮杂硼烷库来自一种常见的原材料。
• Toward Efficient Nucleophilic Azaborine Building Blocks for the Synthesis of B–N Naphthyl (Hetero)arylmethane Isosteres
  作者：Javad Amani、Gary A. Molander

  DOI：10.1021/acs.orglett.5b01750

  日期：2015.7.17

  To develop a method for the synthesis of a class of azaborines, potassium 2-(trifluoroboratomethyl)-2,1-borazaronaphthalenes have been synthesized to serve as nucleophilic building blocks. In palladium-catalyzed cross-coupling reactions with (hetero)aryl chlorides they serve to produce a variety of pseudobenzylic (hetero)aryl substituted azaborines. Potassium 2-(trifluoroboratomethyl)-2,1-borazaronaphthalenes are crystalline solids that are more Stable than 2-(chloromethyl)-2,1-borazaronaphthalenes and have a broader substrate scope in cross-coupling reactions compared to their pseudobenzylic chloride counterparts.
• Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
  作者：Gary A. Molander、Steven R. Wisniewski、Javad Amani

  DOI：10.1021/ol502708z

  日期：2014.11.7

  One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This BN isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.