(S)-N-(1-methylethyl)-3-hydroxybutyramide | 134001-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-(1-methylethyl)-3-hydroxybutyramide
• 英文别名: (3S)-3-hydroxy-N-propan-2-ylbutanamide
• CAS: 134001-66-4
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: FWTIUOSXIWTFNW-LURJTMIESA-N

物化性质

• 沸点：
  303.4±25.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-methylethyl)-3-hydroxybutyramide 在 硼烷四氢呋喃络合物 、 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 (S)-(2u,6l,1'u)-2-(1',3'-dimethylbutyl)-6-methyl-3-(1-methylethyl)-1,3,2-oxazaphosphorinane 2-oxide
  参考文献：
  名称：

  Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions

  摘要：

  A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.

  DOI：

  10.1021/ja00153a009
• 作为产物：
  描述：

  3-羟基丁酸乙酯 、 异丙胺 在 三甲基铝 作用下， 生成 (S)-N-(1-methylethyl)-3-hydroxybutyramide
  参考文献：
  名称：

  Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions

  摘要：

  A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.

  DOI：

  10.1021/ja00153a009

文献信息

• Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions
  作者：Scott E. Denmark、Chien-Tien Chen

  DOI：10.1021/ja00153a009

  日期：1995.12

  A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.