2-iodo-4,5-dimethylbenzyl bromide | 293732-27-1

• 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-iodo-4,5-dimethylbenzyl bromide
• 英文别名: 1-(Bromomethyl)-2-iodo-4,5-dimethylbenzene
• CAS: 293732-27-1
• 化学式: C₉H₁₀BrI
• 分子量: 324.987
• InChiKey: HBKUQBKVXBRFHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-iodo-4,5-dimethylbenzyl bromide 在 nickel(II) iodide 、 2-phenyl-1,10-phenanthroline 、 sodium iodide 、 一氧化二氮 、 锌 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 25.0 ℃ 、253.33 kPa 条件下， 反应 40.0h， 生成 C₁₃H₁₈O
  参考文献：
  名称：

  Ni-Catalyzed Oxygen Transfer from N₂O onto sp³-Hybridized Carbons

  摘要：

  DOI：

  10.1021/jacs.2c06227
• 作为产物：
  描述：

  3,4-二甲基苯甲醇 在 碘 、 silver trifluoroacetate 、 三溴化磷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 2-iodo-4,5-dimethylbenzyl bromide
  参考文献：
  名称：

  Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems

  摘要：

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.

  DOI：

  10.1021/ol034194+

文献信息

• Stereoretentive Intramolecular Glycosyl Cross-Coupling: Development, Scope, and Kinetic Isotope Effect Study
  作者：Duk Yi、Feng Zhu、Maciej A. Walczak

  DOI：10.1021/acs.orglett.8b01927

  日期：2018.8.3

  A series of cyclic C-glycosides were synthesized using the palladium-catalyzed stereoretentive intramolecular glycosylation of aryl iodides by employing a bulky phosphine ligand. A variety of functional groups are tolerated in the reaction, and enantioenriched anomeric nucleophiles could be coupled without erosion of optical purity. This study offers a unified method to access both cis- and trans-fused

  通过使用庞大的膦配体，使用钯催化的芳基碘的立体保留分子内糖基化合成了一系列环状C-糖苷。反应中允许使用多种官能团，并且对映体富集的异头亲核试剂可以在不损害光学纯度的情况下偶联。这项研究提供了一种通过利用 Stille 反应的立体保持性来访问顺式和反式稠环的统一方法。此外，分子间和分子内交叉偶联的竞争实验显示，二次 KIE 分别为 1.43 和 0.81，表明在过渡态存在截然不同的空间拥塞。
• Metalation–cyclisation sequence on N-(o-halobenzyl)pyrroles. Synthesis of pyrrolo[1,2-b]isoquinolones
  作者：Ainhoa Ardeo、Esther Lete、Nuria Sotomayor

  DOI：10.1016/s0040-4039(00)00817-0

  日期：2000.7

  Parham-type cyclisation of N-(o-halobenzyl)pyrroles has been investigated. Aryllithiums generated from metalation of N-(o-iodobenzyl)pyrroles undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolinones in moderate to good yields, if the N,N-diethylcarbamoyl group is used as internal electrophile and the aromatic ring is activated.

  已经研究了N-（邻卤代苄基）吡咯的Parham型环化。如果将N，N-二乙基氨基甲酰基用作内部亲电试剂和芳环，则由N-（邻碘苄基）吡咯金属化生成的芳基锂分子内环化，可以中等至良好的产率得到吡咯并[1,2- b ]异喹啉酮被激活。
• Truce‐Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids
  作者：Yu Wang、Wanying Pan、Yuxuan Zhang、Limin Wang、Jianwei Han

  DOI：10.1002/anie.202304897

  日期：2023.7.10

  A novel iodonium Truce-Smiles rearrangement featuring an aryl transfer from I to C pathway was developed, where no metal- or photo-catalysts are needed. The interaction between ionic liquids and diaryliodonium salts largely contributed to the efficiency of the reaction under mild conditions. This method furnished 64 examples of sulfonyl substituted ortho-iodo diarylmethanes as potentially valuable

  开发了一种新型碘鎓 Truce-Smiles 重排，其特征是芳基从 I 途径转移到 C 途径，不需要金属或光催化剂。离子液体和二芳基碘盐之间的相互作用很大程度上提高了温和条件下的反应效率。该方法提供了 64 个磺酰基取代的邻碘二芳基甲烷的实例，作为有机合成中具有潜在价值的构建单元。
• Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems
  作者：Javier Ruiz、Nuria Sotomayor、Esther Lete

  DOI：10.1021/ol034194+

  日期：2003.4.1

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.
• Cascade Reactions: A Multicomponent Approach to Functionalized Indane Derivatives by a Tandem Palladium- Catalyzed Carbamoylation/Carbocylization Process
  作者：Bartolo Gabriele、Lucia Veltri、Raffaella Mancuso、Carla Carfagna

  DOI：10.1002/adsc.201301051

  日期：2014.8.11

  AbstractA novel, multicomponent and stereoselective approach to functionalized indane derivatives is reported. It is based on a tandem process consisting of Pd‐catalyzed oxidative carbamoylation of 2‐(2‐ethynylbenzyl)malonates with carbon monoxide, a secondary amine, and oxygen (with formation of a propiolamide intermediate), followed by carbocyclization, occurring through intramolecular addition of an in situ formed carbanion to the propiolamide moiety.magnified image