5-bromo-N-phenylhexanamide

• 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: 5-bromo-N-phenylhexanamide
• 化学式: C₁₂H₁₆BrNO
• 分子量: 270.169
• InChiKey: OFLBJQQFLVACJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-N-phenylhexanamide 、 乙基溴苯 在 乙二醇二甲醚溴化镍 、 锰 、 4-chloro-2,6-di(4,5-dihydro-1,3-oxazol-2-yl)-pyridine 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72 %的产率得到5-methyl-N,7-diphenylheptanamide
  参考文献：
  名称：

  Ligand‐Controlled Nickel‐Catalyzed Regiodivergent Cross‐Electrophile Alkyl‐Alkyl Couplings of Alkyl Halides

  摘要：

  AbstractFunctionalizing specific positions on a saturated alkyl molecule is a key challenge in synthetic chemistry. Herein, a ligand‐controlled regiodivergent alkylations of alkyl bromides at different positions by Ni‐catalyzed alkyl‐alkyl cross‐electrophile coupling with the second alkyl bromides has been developed. The reaction undergoes site‐selective isomerization on one alkyl bromides in a controlled manner, providing switchable access to diverse alkylated structures at different sites of alkyl bromides. The reaction occurs at three similar positions with excellent chemo‐ and regioselectivity, representing a remarkable ligand tuned reactivity between alkyl‐alkyl cross‐coupling and nickel migration along the hydrocarbon side chain. This reaction offers a catalytic platform to diverse saturated architectures by alkyl‐alkyl bond‐formation from identical starting materials.

  DOI：

  10.1002/anie.202215779
• 作为产物：
  描述：

  丁位己内酯 在 草酰氯 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-bromo-N-phenylhexanamide
  参考文献：
  名称：

  Ligand‐Controlled Nickel‐Catalyzed Regiodivergent Cross‐Electrophile Alkyl‐Alkyl Couplings of Alkyl Halides

  摘要：

  AbstractFunctionalizing specific positions on a saturated alkyl molecule is a key challenge in synthetic chemistry. Herein, a ligand‐controlled regiodivergent alkylations of alkyl bromides at different positions by Ni‐catalyzed alkyl‐alkyl cross‐electrophile coupling with the second alkyl bromides has been developed. The reaction undergoes site‐selective isomerization on one alkyl bromides in a controlled manner, providing switchable access to diverse alkylated structures at different sites of alkyl bromides. The reaction occurs at three similar positions with excellent chemo‐ and regioselectivity, representing a remarkable ligand tuned reactivity between alkyl‐alkyl cross‐coupling and nickel migration along the hydrocarbon side chain. This reaction offers a catalytic platform to diverse saturated architectures by alkyl‐alkyl bond‐formation from identical starting materials.

  DOI：

  10.1002/anie.202215779

文献信息

• Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis
  作者：Hai‐Wu Du、Yi‐Dan Du、Xian‐Wang Zeng、Wei Shu

  DOI：10.1002/anie.202308732

  日期：2023.9.18

  Catalytic methods for direct access to aliphatic trifluoromethyl ketones from feedstocks remain underdeveloped, partially owing to the high reactivity and instability of the trifluoroacetyl radical. Reported herein is the photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides and trifluoroacetic anhydride. The reaction features visible-light catalysis and halogen-atom transfer (XAT)

  从原料中直接获取脂肪族三氟甲基酮的催化方法仍然不发达，部分原因是三氟乙酰基的高反应活性和不稳定性。本文报道了从烷基溴和三氟乙酸酐光催化合成三氟甲基酮。该反应的特点是可见光催化和卤素原子转移（XAT），然后使烷基自由基与稳定的三氟乙酰基自由基发生自由基-自由基交叉偶联。
• CN116396209
  申请人：——

  公开号：——

  公开（公告）日：——