2,2-dichloro-3-methyl-butanoic acid | 76043-73-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,2-dichloro-3-methyl-butanoic acid
• 英文别名: 2,2-Dichloro-3-methylbutanoic acid
• CAS: 76043-73-7
• 化学式: C₅H₈Cl₂O₂
• 分子量: 171.023
• InChiKey: DWAXDEKLXIKTOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-3-methyl-butanoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-dichloro-3-methylbutanoyl chloride
  参考文献：
  名称：

  Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe0-FeCl3 or CuCl-TMEDA

  摘要：

  The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe-0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00908-3
• 作为产物：
  描述：

  2,2-二氯-3-甲基丁醛 在 硝酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 360.0h， 以72%的产率得到2,2-dichloro-3-methyl-butanoic acid
  参考文献：
  名称：

  Oxidation of Aliphatic 2,2‐Dichloroalkanals by HNO₃ in CH₂Cl₂: An Easy and Eco‐friendly Route to the Corresponding 2,2‐Dichloroalkanoic Acids

  摘要：

  A simple, economically convenient, and eco-compatible procedure for the oxidation of 2,2-dichloroalkanals to the corresponding alkanoic acids has been set up, employing HNO3 in CH2Cl2, in the presence of NaNO2 as catalyst.

  DOI：

  10.1081/scc-120030698

文献信息

• Buyck, L. De; Verhe, R.; Kimpe, N. De, Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 6, p. 441 - 458
  作者：Buyck, L. De、Verhe, R.、Kimpe, N. De、Courtheyn, D.、Schamp, N.

  DOI：——

  日期：——
• Bellesia, Franco; De Buyck, Laurent; Ghelfi, Franco, Synlett, 2000, # 1, p. 146 - 148
  作者：Bellesia, Franco、De Buyck, Laurent、Ghelfi, Franco

  DOI：——

  日期：——
• The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-allyl-N-benzyl-2,2-dihaloamides to γ-lactams. Application to the stereoselective synthesis of pilolactam
  作者：Franco Ghelfi、Franco Bellesia、Luca Forti、Gianluca Ghirardini、Romano Grandi、Emanuela Libertini、Maria C Montemaggi、Ugo M Pagnoni、Adriano Pinetti、Laurent De Buyck、Andrew F Parsons

  DOI：10.1016/s0040-4020(99)00247-1

  日期：1999.4

  A number of N-benzylic protecting groups and allylic substituents have been investigated for the rearrangement, promoted by CuCl-TMEDA, of N-allyl-2,2-dihaloamides to 3,4-disubstituted gamma-lactams. An appreciable chiral induction was observed at the C-4 site when alpha-phenylethylamine was used as a chiral protecting group, while an unexpected Diels-Alder reaction occurred when using a 2-furyl-methyl protection. This rearrangement has been applied to the synthesis of pilolactam, a drug with muscarinic activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• BUYCK L. DE; KIMPE N. DE; COURTHEYN D.; SCHAMP N., BULL. SOC. CHIM. BELG., 1980, 89, NO 6, 441-458
  作者：BUYCK L. DE、 KIMPE N. DE、 COURTHEYN D.、 SCHAMP N.

  DOI：——

  日期：——
• Oxidation of Aliphatic 2,2‐Dichloroalkanals by HNO₃ in CH₂Cl₂: An Easy and Eco‐friendly Route to the Corresponding 2,2‐Dichloroalkanoic Acids
  作者：Franco Bellesia、Laurent De Buyck、Franco Ghelfi、Ugo M. Pagnoni、Paolo Strazzolini

  DOI：10.1081/scc-120030698

  日期：2004.12.31

  A simple, economically convenient, and eco-compatible procedure for the oxidation of 2,2-dichloroalkanals to the corresponding alkanoic acids has been set up, employing HNO3 in CH2Cl2, in the presence of NaNO2 as catalyst.