ethyl 3-hydroxy-2,3,4,4-tetramethylpentanoate | 174358-65-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 3-hydroxy-2,3,4,4-tetramethylpentanoate
• 英文别名: ethyl 3-hydroxy-2,4,4-trimethylpentanoate
• CAS: 174358-65-7
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: UUZSZHDFNAQHDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  259.8±13.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-2,3,4,4-tetramethylpentanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以84%的产率得到2,4,4-trimethyl-1,3-pentanediol
  参考文献：
  名称：

  BCl₃- and TiCl₄-Mediated Reductions of β-Hydroxy Ketones

  摘要：

  Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.

  DOI：

  10.1021/jo951549x
• 作为产物：
  描述：

  特戊醛 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 生成 ethyl 3-hydroxy-2,3,4,4-tetramethylpentanoate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029

文献信息

• Stereoselective reduction of 2-methyl-3-oxo esters (or amides) with sodium borohydride catalyzed by manganese(II) chloride or tetrabutylammonium borohydride. A practical preparation of erythro and threo-3-hydroxy-2-methyl esters (or amides)
  作者：Masahiko Taniguchi、Hideaki Fujii、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4020(01)81804-4

  日期：1993.1

  lpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 2-methyl-3-oxo esters or 2-methyl-3-oxo amides in the presence of a catalytic amount of manganese(II) chloride. On the other hand, reduction of these substrates with n-Bu4NBH4 provided threo-isomers selectively. erythro-Selective reduction of 2-methyl-3-oxo amides with NaBH3CN in 1N HCl-MeOH is also described

  赤-3-羟基-2- methylpropionates或赤-3-羟基-2-甲基丙酰胺用高立体选择性加入NaBH制备4减少在相应的2-甲基-3-氧代酯或2-甲基-3-氧代酰胺的催化量的氯化锰（II）的存在。另一方面，用n -Bu 4 NBH 4还原这些底物选择性地提供了苏式异构体。还描述了在1N HCl-MeOH中用NaBH 3 CN对2-甲基-3-氧代酰胺的赤型选择性还原。
• Catalytic Diastereoselective Reductive Aldol Reaction:  Optimization of Interdependent Reaction Variables by Arrayed Catalyst Evaluation
  作者：Steven J. Taylor、James P. Morken

  DOI：10.1021/ja992952e

  日期：1999.12.1