methyl 2,2-dichloro-3-methylbutanoate | 73506-85-1

• 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: methyl 2,2-dichloro-3-methylbutanoate
• CAS: 73506-85-1
• 化学式: C₆H₁₀Cl₂O₂
• 分子量: 185.05
• InChiKey: ZRUHXSIMIXNRDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  65-66 °C(Press: 11 Torr)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dichloro-3-methylbutanoate 在 lithium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 生成 2,2-dichloro-3-methyl-butanoic acid
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(99)00247-1
• 作为产物：
  描述：

  2-Chloro-1,1-dimethoxy-3-methyl-butane 在 三甲基氯硅烷 、 三氯异氰尿酸 、 lithium methanolate 作用下， 以 乙腈 为溶剂， 反应 27.0h， 生成 methyl 2,2-dichloro-3-methylbutanoate
  参考文献：
  名称：

  Preparation of 2,2-Dihalocarboxylic Acid Methyl Esters by Oxidation–Chlorination of 2-(1-Haloalkyl)-4-methyl-1,3-dioxolanes with Trichloroisocyanuric Acid

  摘要：

  通过 2-（1-卤代烷基）-4-甲基-1,3-二氧戊环与三氯异氰尿酸的氧化-氯化反应，可以获得收率极高的 2,2-二氯或 2-溴-2-氯羧酸甲酯。

  DOI：

  10.1246/bcsj.67.1622

文献信息

• Halogen atom transfer radical addition of α-polychloroesters to olefins promoted by Fe0 filings
  作者：Luca Forti、Franco Ghelfi、Emanuela Libertini、Ugo M. Pagnoni、Ercole Soragni

  DOI：10.1016/s0040-4020(97)10241-1

  日期：1997.12

  The Kharasch addition of methyl 2,2-dichlorocarboxylates or trichloro acetic acid derivatives to alkenes, affording the corresponding 1:1 adducts, is promoted by the iron filings/N,N-dimethylformamide system.

  铁屑/ N，N-二甲基甲酰胺体系促进了2，2-二氯羧酸甲酯或三氯乙酸衍生物在链烯烃上的Kharasch加成反应，得到相应的1：1加合物。
• N-(2-Hydroxyalkyl)-2,2-dihaloamides by Amino-de-alkoxylation of Methyl 2,2-Dihalocarboxylates
  作者：L. Forti、F. Ghelfi、R. Grandi、E. Libertini、U. M. Pagnoni

  DOI：10.1080/00397919608003760

  日期：1996.10

  Abstract The chemoselective N-acylation of 2-amino alcohols with methyl 2,2-dichloro carboxylates occurs smoothly and in excellent yields.

  摘要 2-氨基醇与2,2-二氯羧酸甲酯的化学选择性N-酰化反应顺利且产率高。
• Methyl α,α-dichloro-esters by oxidation-chlorination of cyclic acetals with trichloroisocyanuric acid
  作者：Franco Bellesia、Monica Boni、Franco Ghelfi、Ugo M. Pagnoni

  DOI：10.1016/s0040-4039(00)76672-x

  日期：1994.5

  Methyl α-chloro- or α,α-dichloro-esters are obtained in excellent yields by oxidation chlorination of 2-alkyl-4,5-dimethyl-1,3-dioxolanes with trichloroisocyanuric acid.

  通过用三氯异氰尿酸氧化2-烷基-4,5-二甲基-1,3-二氧戊环，可以以优异的产率获得甲基α-氯-或α，α-二氯酯。
• Zinc Promoted Addition of Methyl 2,2-Dihalocarboxylates to Carbonyl Compounds
  作者：Marta Benincasa、Luca Forti、Franco Ghelfi、Emanuela Libertini、Ugo M. Pagnoni

  DOI：10.1080/00397919608004648

  日期：1996.11

  Abstract Methyl 2,2-dihalocarboxylates add easily to carbonyl compounds in fair to good yields through the intermediate formation of 2-haloester enolates; the reaction is promoted by zinc, following a “Barbier” type procedure.

  摘要 2,2-二卤代羧酸甲酯通过中间体形成2-卤代酯烯醇化物，很容易以一般到良好的收率加成到羰基化合物中；该反应由锌促进，遵循“Barbier”型程序。
• Amino-de-Alkoxylation of Methyl 2,2-Dihalocarboxylates
  作者：Luca Porti、Franco Ghelfi、Francesca Munari、Ugo M. Pagnoni

  DOI：10.1016/0040-4020(95)00774-3

  日期：1995.11

  N-alkyl-2,2-dihaloamides were efficiently prepared by amino-de-alkoxylation of methyl 2,2-dihalocarboxylates, at room temperature without solvents and promoters. Excellent yields of anilides were obtained after addition of AlCl3.

  N-烷基-2,2-二卤代酰胺是通过在室温下不使用溶剂和促进剂的情况下，对2,2-二卤代羧酸甲酯进行氨基脱烷氧基化反应而有效制备的。加入AlCl 3后，可获得优异的苯甲酸酯收率。