2-bromobenzaldehyde O-methyloxime | 1135444-69-7

• 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: 2-bromobenzaldehyde O-methyloxime
• 英文别名: 1-(2-bromophenyl)-N-methoxymethanimine
• CAS: 1135444-69-7
• 化学式: C₈H₈BrNO
• 分子量: 214.062
• InChiKey: PXYSQHPPUBKPHG-UHFFFAOYSA-N

物化性质

• 沸点：
  254.5±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromobenzaldehyde O-methyloxime 在 盐酸 、 2-picoline borane 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以85%的产率得到N-(2-bromobenzyl)-O-methylhydroxylamine
  参考文献：
  名称：

  One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex

  摘要：

  Reduction of oxime ethers with a 2-picoline-borane complex was examined to give alkoxyamine derivatives. The reduction was found to proceed in the presence of aqueous HCl in MeOH-AcOH. The method was extended to one-pot synthesis of alkoxyamine derivatives from aldehydes and ketones. The reaction of carbonyl compounds with alkoxyamines in MeOH-AcOH (10:1), followed by sequential treatment with 2-picoline-borane and 3M HCl afforded alkoxyamine derivatives in good yields. This procedure can be applied to the synthesis of various alkoxyamine derivatives from aliphatic/aromatic aldehydes and ketones.

  DOI：

  10.3987/com-08-11532
• 作为产物：
  描述：

  benzaldehyde O-methyloxime 在 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-bromobenzaldehyde O-methyloxime
  参考文献：
  名称：

  Selectiveortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C–H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes

  摘要：

  Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.

  DOI：

  10.1021/jo200853j

文献信息

• Ir-Catalyzed Cascade C–H Fusion of Aldoxime Ethers and Heteroarenes: Scope and Mechanisms
  作者：Zhiqian Yu、Yan Zhang、Junbin Tang、Luoqiang Zhang、Qianhui Liu、Qian Li、Ge Gao、Jingsong You

  DOI：10.1021/acscatal.9b04274

  日期：2020.1.3

  of phenanthridine derivatives is achieved by an iridium-catalyzed direct fusion of oxime ethers and heteroarenes, which is a successful example of a cascade C–H/C–H cross-coupling/cyclization strategy for polycyclic heteroaromatic synthesis. By subtle tuning of the reaction conditions, both benzo- and simple five-membered heteroarenes are suitable substrates under similar but different conditions. The

  通过铱催化肟醚和杂芳烃的直接融合，可实现菲啶衍生物的简明合成，这是多环杂芳族合成的级联C–H / C–H交叉偶联/环化策略的成功实例。通过微调反应条件，在相似但不同的条件下，苯并五元杂芳基和简单的五元杂芳基都是合适的底物。关键是正确选择银盐。详细的机理研究表明，第一步C–H / C–H交叉偶联步骤涉及[Ir II ] – [Ir IV ]催化循环，需要Ag 2 O作为氧化剂。对于第二个环化步骤，自由基过程控制了苯并杂芳烃和Ag 2的反应O是必需的；然而，在涉及[Ir I ]-[Ir III ]催化循环的简单五元杂芳烃的反应中，C–H环化作用是必要的，而AgTFA是必需的。
• Pd-catalyzed dehydrogenative C–H activation of iminyl hydrogen with the indole C3–H and C2–H bond: an elegant synthesis of indeno[1,2-b]indoles and indolo[1,2-a]indoles
  作者：Somjit Hazra、Biplab Mondal、Rajendra Narayan De、Brindaban Roy

  DOI：10.1039/c4ra16661b

  日期：——

  This synthetic protocol describes two sequential C–H activation route towards indeno[1,2-b]indoles. Indolo[1,2-a]indoles were also synthesized by activating indole C2–H bond.

  这个合成方案描述了两个顺序的C-H活化路线，用于制备indeno [1,2-b] indoles。通过激活吲哚C2-H键，也可以合成吲哚[1,2-a]吲哚。
• Copper- and Palladium-Cocatalyzed Intramolecular C-H Functionalization/C-N Bond Formation: A Route to the Synthesis of Indoloisoquinoline Derivatives
  作者：Somjit Hazra、Biplab Mondal、Habibur Rahaman、Brindaban Roy

  DOI：10.1002/ejoc.201301699

  日期：2014.5

  A Cu and Pd bi-catalytic system is found to be very effective for the indole C2–H functionalization/C–N bond formation process.This is a unique reaction in which isoquinoline systems were synthesized from aldoximes rather than from ketoximes. During the reaction Cu(OTf)2 converts the aldoximes into the corresponding cyanides and indoloisoquinolines, but introduction of Pd(OAc)2 changes the outcome

  发现 Cu 和 Pd 双催化体系对吲哚 C2-H 官能化/C-N 键形成过程非常有效。这是一种独特的反应，其中异喹啉体系由醛肟合成，而不是由酮肟合成。在反应过程中，Cu(OTf)2 将醛肟转化为相应的氰化物和吲哚异喹啉，但 Pd(OAc)2 的引入通过抑制氰基产物的形成显着改变了反应结果，从而仅产生吲哚异喹啉。一系列取代的吲哚异喹啉和氮杂吲哚异喹啉在空气中以良好到非常好的产率制备。
• One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex
  作者：Tsutomu Yokomatsu、Yasushi Kawase、Takehiro Yamagishi、Teruo Kutsuma、Kimio Ueda、Takeo Iwakuma、Tadashi Nakata

  DOI：10.3987/com-08-11532

  日期：——

  Reduction of oxime ethers with a 2-picoline-borane complex was examined to give alkoxyamine derivatives. The reduction was found to proceed in the presence of aqueous HCl in MeOH-AcOH. The method was extended to one-pot synthesis of alkoxyamine derivatives from aldehydes and ketones. The reaction of carbonyl compounds with alkoxyamines in MeOH-AcOH (10:1), followed by sequential treatment with 2-picoline-borane and 3M HCl afforded alkoxyamine derivatives in good yields. This procedure can be applied to the synthesis of various alkoxyamine derivatives from aliphatic/aromatic aldehydes and ketones.
• Selective<i>ortho</i>-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C–H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes
  作者：Emmanuelle Dubost、Christine Fossey、Thomas Cailly、Sylvain Rault、Frederic Fabis

  DOI：10.1021/jo200853j

  日期：2011.8.5

  Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.