α-chloro-3-nitroacetophenone dimethyl acetal | 1181216-70-5

• 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: α-chloro-3-nitroacetophenone dimethyl acetal
• 英文别名: 1-(2-chloro-1,1-dimethoxyethyl)-3-nitrobenzene；1-(2-Chloro-1,1-dimethoxyethyl)-3-nitrobenzene
• CAS: 1181216-70-5
• 化学式: C₁₀H₁₂ClNO₄
• 分子量: 245.663
• InChiKey: LZHCINZVKBXQBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 间硝基苯甲醛 在 哌啶 、 1,3-二氯-5,5-二甲基海因 作用下， 反应 12.0h， 以91%的产率得到α-chloro-3-nitroacetophenone dimethyl acetal
  参考文献：
  名称：

  One-Step Conversion of Acetophenones to α-Haloacetophenone Dimethyl Acetals Using DCDMH/DBDMH and Molecular Sieve in Methanol

  摘要：

  Using DCDMH/DBDMH as N-halo reagent, piperidine as catalyst, and 4-A molecular sieve as water-removing agent, alpha-haloacetophenone dimethyl acetals were directly obtained from the solvent of methanol. As to the substrates with electron-withdrawing groups, the conversions were 80-100%.

  DOI：

  10.1080/00397911.2010.540696

文献信息

• Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH
  作者：Zizhan Chen、Bin Zhou、Huihua Cai、Wei Zhu、Xinzhuo Zou

  DOI：10.1039/b815169e

  日期：——

  New processes that can selectively prepare α-mono or α,α-dichloro ketones and β-ketoesters using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) are reported. Using silica gel as the catalyst and methanol as the solvent and heating for 1 h under reflux, α-monochlorinated products were selectively obtained in 86–98% yield. However using a deep eutectic solvent (choline chloride: p-TsOH = 1:1) as the solvent

  可以选择性地制备α-单或α，α-二氯的新工艺 酮类 和β-酮酸酯使用 1,3-二氯-5,5-二甲基乙内酰脲（DCDMH）。使用硅石 凝胶为 催化剂 和 甲醇 作为 溶剂回流加热1小时，有选择地获得α-一氯代产物，收率86-98％。但是使用深共晶溶剂 （氯化胆碱：p -TsOH = 1：1）作为溶剂 室温下搅拌45分钟，可以选择性地获得α，α-二氯化产物，产率为86-95％。
• Mild and Efficient α-Chlorination of Carbonyl Compounds Using Ammonium Chloride and Oxone (2KHSO₅·KHSO₄·K₂SO₄)
  作者：Peraka Swamy、Macharla Arun Kumar、Marri Mahender Reddy、Nama Narender

  DOI：10.1246/cl.2012.432

  日期：2012.4.5

  A simple protocol for the α-monochlorination of ketones and 1,3-dicarbonyl compounds utilizing NH4Cl as a source of chlorine and Oxone as an oxidant in methanol without catalyst is presented. The reaction proceeds at ambient temperature in yields ranging from moderate to excellent.

  提出了一种简单的酮和1,3-二羰基化合物的α-单氯化反应方案，使用NH4Cl作为氯源，Oxone作为氧化剂，在无催化剂的甲醇中进行。反应在室温下进行，产率从中等至优异不等。
• A One-Pot Method Synthesis of α-Chloroketone Dimethyl Acetals
  作者：Zhou Zhong-shi、Li Li、He Xue-han

  DOI：10.3184/174751913x13794472538108

  日期：2013.10

  been developed for the direct preparation of α-chloroketone dimethyl acetals from ketones using ammonium chloride as the source of chlorine and potassium monoperoxysulfate as the oxidant in the presence of trimethyl orthoformate in methanol at room temperature. Ketones which have electron-withdrawing groups on the aryl rings gave the corresponding α-chloroketone dimethyl acetals in moderate to good yields

  开发了一种新的一锅法，用于在室温下，在原甲酸三甲酯的甲醇中，以氯化铵为氯源，单过硫酸钾为氧化剂，由酮直接制备 α-氯酮二甲基缩醛。在芳环上具有吸电子基团的酮以中等至良好的产率得到相应的α-氯酮二甲基缩醛。
• One-Step Conversion of Acetophenones to <font>α</font>-Haloacetophenone Dimethyl Acetals Using DCDMH/DBDMH and Molecular Sieve in Methanol
  作者：Bin Zhou、Zizhan Chen、Zubiao Zheng、Bingbing Han、Xinzhuo Zou

  DOI：10.1080/00397911.2010.540696

  日期：2012.5.15

  Using DCDMH/DBDMH as N-halo reagent, piperidine as catalyst, and 4-A molecular sieve as water-removing agent, alpha-haloacetophenone dimethyl acetals were directly obtained from the solvent of methanol. As to the substrates with electron-withdrawing groups, the conversions were 80-100%.