4,4,4-trichloro-3-hydroxy-2-methylbutanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-trichloro-3-hydroxy-2-methylbutanal
• 英文别名: 4,4,4-Trichloro-3-hydroxy-2-methylbutanal
• 化学式: C₅H₇Cl₃O₂
• 分子量: 205.468
• InChiKey: QWHHTYQEQFMZLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 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：

  4,4,4-trichloro-3-hydroxy-2-methylbutanal 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 4,4,4-trichloro-2-methyl-crotonaldehyde
  参考文献：
  名称：

  Highly stereoselective bioreduction and one-way isomerization of 2-alkyl-4,4,4-trichloro-2-butenals

  摘要：

  This article describes a highly stereoselective bioreduction of 2-alkyl-4,4,4-trichloro-2-butenals (1a: Me, 1b: Ell mediated by baker's yeast (Saccharomyces cerevisiae). The E-isomers were regiospecifically converted into the saturated alcohols 2 with high enantioselectivity, whereas the Z-isomers generated in situ by a competitive one-way isomerization were reduced only into the corresponding allyl alcohols 3 during the reactions. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.115
• 作为产物：
  描述：

  丙醛 、 三氯乙醛 在 L-脯氨酰胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到4,4,4-trichloro-3-hydroxy-2-methylbutanal
  参考文献：
  名称：

  氯醛与脂肪醛的高选择性催化交叉羟醛反应

  摘要：

  描述了一种有效的 β-三氯甲基-β-羟基醛合成方法。使用哌啶或L-脯氨酰胺作为催化剂，氯醛与脂肪醛的直接交叉羟醛反应在室温下顺利进行。以高产率（高达 95%）分离交叉羟醛缩合产物，并且在 L-脯氨酰胺的情况下观察到中等至高的对映选择性（高达 88% ee）。

  DOI：

  10.1055/s-2006-948164

文献信息

• Asymmetric Aldol Reaction of Chloral Catalyzed by Diarylprolinol
  作者：Yujiro Hayashi、Shoya Watanabe、Yusuke Yasui、Shigenobu Umemiya

  DOI：10.1002/cctc.201500282

  日期：2015.6.1

  The asymmetric cross‐aldol reaction of chloral hydrate with aldehyde pronucleophiles catalyzed by a trifluoromethyl‐substituted diarylprolinol was accomplished to afford γ‐trichloro‐β‐hydroxy aldehydes in good yields with excellent enantioselectivities. The resulting aldehyde products were converted into chiral α‐azido, α‐(4‐methyl)phenoxy, and α‐fluoro esters without a loss in the diastereo‐ or enantioselectivities

  由三氟甲基取代的二芳基脯氨醇催化的水合氯醛与醛类亲核试剂的不对称交叉羟醛反应可以得到高收率的γ-三氯-β-羟基醛，且具有出色的对映选择性。所得醛产物被转化为手性α-叠氮基，α-（4-甲基）苯氧基和α-氟代酯，而对映选择性或对映选择性没有损失。
• Highly Selective Catalytic Cross-Aldol Reactions of Chloral with Aliphatic Aldehydes
  作者：Yuefa Gong、Fanglin Zhang、Ning Su

  DOI：10.1055/s-2006-948164

  日期：2006.7

  An efficient synthetic method for β-trichloromethyl-β-hydroxy aldehydes is described. Using piperidine or L-prolinamide as the catalyst, direct cross-aldol reactions of chloral with aliphatic aldehydes occur smoothly at room temperature. The cross-aldol condensation products are isolated in high yields (up to 95%), and a moderate to high enantioselectivity (up to 88% ee) is observed in the case of

  描述了一种有效的 β-三氯甲基-β-羟基醛合成方法。使用哌啶或L-脯氨酰胺作为催化剂，氯醛与脂肪醛的直接交叉羟醛反应在室温下顺利进行。以高产率（高达 95%）分离交叉羟醛缩合产物，并且在 L-脯氨酰胺的情况下观察到中等至高的对映选择性（高达 88% ee）。
• Highly stereoselective bioreduction and one-way isomerization of 2-alkyl-4,4,4-trichloro-2-butenals
  作者：Ning Li、Fanglin Zhang、Yuefa Gong

  DOI：10.1016/j.tetlet.2007.01.115

  日期：2007.3

  This article describes a highly stereoselective bioreduction of 2-alkyl-4,4,4-trichloro-2-butenals (1a: Me, 1b: Ell mediated by baker's yeast (Saccharomyces cerevisiae). The E-isomers were regiospecifically converted into the saturated alcohols 2 with high enantioselectivity, whereas the Z-isomers generated in situ by a competitive one-way isomerization were reduced only into the corresponding allyl alcohols 3 during the reactions. (c) 2007 Published by Elsevier Ltd.