(+)-R-2-(tert-butoxymethyl)-3-ethoxy-2-methyl-3-oxopropanoic acid | 289719-76-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-R-2-(tert-butoxymethyl)-3-ethoxy-2-methyl-3-oxopropanoic acid
• 英文别名: (2R)-3-ethoxy-2-methyl-2-[(2-methylpropan-2-yl)oxymethyl]-3-oxopropanoic acid
• CAS: 289719-76-2
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: GDBLDTLOZMVPQI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-R-2-(tert-butoxymethyl)-3-ethoxy-2-methyl-3-oxopropanoic acid 在 palladium on activated charcoal 甲醇 、 sodium tetrahydroborate 、 氯化亚砜 、 三氟甲磺酸 、 potassium tert-butylate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， -78.0~40.0 ℃ 、500.0 kPa 条件下， 反应 42.0h， 生成 (+)-S-3-(hydroxymethyl)-3-methyl-2-oxetanone
  参考文献：
  名称：

  A New Synthetic Route to β-Unsubstituted β-Lactones by Intramolecular Cyclization

  摘要：

  When carboxylic acids beta-substituted by a tert-butoxy group were treated with thionyl chloride, an intermediate acyl chloride beta-substituted by a hydroxyl group was likely formed. Its subsequent intramolecular cyclization produced novel beta-lactones in one step. Two enantiomerically enriched lactones could be prepared via intermediates obtained by enzymatic hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00313-6
• 作为产物：
  描述：

  2-[(叔丁氧基)甲基]-2-甲基丙二酸二乙酯 在 sodium hydroxide 作用下， 以 phosphate buffer 为溶剂， 生成 (+)-R-2-(tert-butoxymethyl)-3-ethoxy-2-methyl-3-oxopropanoic acid 、 (-)-S-2-(tert-butoxymethyl)-3-ethoxy-2-methyl-3-oxopropanoic acid
  参考文献：
  名称：

  A New Synthetic Route to β-Unsubstituted β-Lactones by Intramolecular Cyclization

  摘要：

  When carboxylic acids beta-substituted by a tert-butoxy group were treated with thionyl chloride, an intermediate acyl chloride beta-substituted by a hydroxyl group was likely formed. Its subsequent intramolecular cyclization produced novel beta-lactones in one step. Two enantiomerically enriched lactones could be prepared via intermediates obtained by enzymatic hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00313-6

文献信息

• A New Synthetic Route to β-Unsubstituted β-Lactones by Intramolecular Cyclization
  作者：François-René Alexandre、Stéphanie Legoupy、François Huet

  DOI：10.1016/s0040-4020(00)00313-6

  日期：2000.6

  When carboxylic acids beta-substituted by a tert-butoxy group were treated with thionyl chloride, an intermediate acyl chloride beta-substituted by a hydroxyl group was likely formed. Its subsequent intramolecular cyclization produced novel beta-lactones in one step. Two enantiomerically enriched lactones could be prepared via intermediates obtained by enzymatic hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.