2-bromo-3-methylbutyraldehyde dimethyl acetal | 98429-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3-methylbutyraldehyde dimethyl acetal
• 英文别名: α-bromo-isovaleraldehyde dimethylacetal；α-Brom-isovaleraldehyd-dimethylacetal；2-Brom-1,1-dimethoxy-3-methyl-butan；2-Bromo-1,1-dimethoxy-3-methylbutane
• CAS: 98429-74-4
• 化学式: C₇H₁₅BrO₂
• 分子量: 211.099
• InChiKey: ZQLMTSUVYBWVEX-UHFFFAOYSA-N

物化性质

• 沸点：
  71-74 °C(Press: 16 Torr)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3-methylbutyraldehyde dimethyl acetal 在 sodium trisilicate 、 magnesium monohydrogen phosphate 、 氢氧化钾 、 氮气 作用下， 140.0~350.0 ℃ 、5.33 kPa 条件下， 生成 1-甲氧基-3-甲基丁-1,3-二烯
  参考文献：
  名称：

  Nasarow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 106,109; engl. Ausg. S. 111, 112

  摘要：

  DOI：
• 作为产物：
  描述：

  异戊醛 在 溴 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 生成 2-bromo-3-methylbutyraldehyde dimethyl acetal
  参考文献：
  名称：

  乙烯酮双（三甲基甲硅烷基）乙缩醛与α-卤代乙缩醛的Mukaiyama反应：便捷的丁烯内酯合成

  摘要：

  使乙烯酮双（三甲基甲硅烷基）乙缩醛与α-卤代乙缩醛反应，得到β-烷氧基-γ-卤代酸，通过与两当量的碱反应将其转化为丁烯化物。这构成了新颖且短的丁烯内酯合成。

  DOI：

  10.1016/s0040-4039(01)93317-9

文献信息

• Stereoselective dehydrobromination of alkyl α-Brα-Cl-carboxylates
  作者：Luca Forti、Franco Ghelfi、Ugo M. Pagnoni

  DOI：10.1016/0040-4039(95)00416-a

  日期：1995.4

  (Z)-Alkyl α-Cl-α,β-unsaturated esters are prepared in excellent yields by stereoselective dehydrobromination of alkyl α-Br-α-Cl-carboxylates with LiClLi2CO3 in dimethylformamide.

  （Z）-烷基α-Cl-α，β-不饱和酯是通过在二甲基甲酰胺中用LiCl 3 Li 2 CO 3对烷基α-Br-α-Cl-羧酸酯进行立体选择性脱氢溴化而制得的。
• An efficient procedure to α-hydroxyaldehyde dimethyl acetals
  作者：Monica Boni、Luca Forti、Franco Ghelfi、Ugo M. Pagnoni

  DOI：10.1016/s0040-4020(01)85273-x

  日期：1994.1

  α-Hydroxyaldehyde dimethyl acetals are prepared efficiently by conversion of α-haloaldehyde dimethyl acetals into α-haloaldehyde hemiacetal acetates and subsequent methanolysis promoted by lithium methoxide.

  通过将α-卤代醛二甲基缩醛转化为α-卤代醛半缩醛乙酸酯并随后通过甲醇锂促进甲醇分解，可有效地制备α-羟基醛二甲基乙缩醛。
• Ketene Chemistry 2.¹A General Procedure for the Synthesis of 2-Alkoxycyclopropane-carboxylic Esters and Acids Starting from Aldehydes and Ketene
  作者：Preben Bødstrup Rasmussen、Søren Bøwadt

  DOI：10.1055/s-1989-27165

  日期：——

  Alkyl 3-alkoxy-4-bromocarboxylates are prepared by the Lewis acid-catalyzed reaction of α-bromoaldehyde acetals with ketene. Base-catalyzed cyclization of these intermediates affords 2-alkoxycyclopropanecarboxylic esters.

  通过Lewis酸催化下的反应，将α-溴醛缩二醇与烯酮反应，制备出烷基3-烷氧基-4-溴羧酸酯。这些中间体在碱催化下发生环化反应，生成2-烷氧基环丙烷羧酸酯。
• Anti-selective reaction of .alpha.-sulfenyl acetals with silylated carbon nucleophiles. Scope, limitation, and mechanism
  作者：Kazuaki Kudo、Yukihiko Hashimoto、Makoto Sukegawa、Masaki Hasegawa、Kazuhiko Saigo

  DOI：10.1021/jo00055a009

  日期：1993.1

  In the presence of a Lewis acid, alpha-sulfenyl acetals 1 reacted with various silylated carbon nucleophiles 2 to give anti adducts (anti-3) with high diastereoselectivity. The stereochemistry was only slightly affected by the reaction conditions, such as temperature, solvent, and Lewis acid. However, the structure of substrate 1 and the kind of nucleophile 2 had considerable effect on the stereochemical course of the reaction. Almost exclusive anti selectivity was attained when 1,1-dimethoxy-2-(tert-butylthio)propane (1b) was used as a substrate or when ketene silyl acetal 2c was employed as a nucleophile. The mechanism of this reaction is essentially S(N)2, although the S(N)1 process participates to a various extent, depending on the structure of substrate 1. The usefulness of this anti-selective reaction was exemplified by the easy transformation of anti-3o to synthetically valuable allylic alcohol anti-6 without any loss of stereochemical information. The reaction of alpha-(benzyloxy)acetal 4 with 2 was also investigated. It gave a syn-rich mixture of diastereomers with lower selectivity.
• Kirrmann et al., Bulletin de la Societe Chimique de France, 1950, p. 707,710
  作者：Kirrmann et al.

  DOI：——

  日期：——