ethyl (2S,3R)-3-[(1S)-1-hydroxyethyl]-2-methyloxirane-2-carboxylate | 950765-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: ethyl (2S,3R)-3-[(1S)-1-hydroxyethyl]-2-methyloxirane-2-carboxylate
• CAS: 950765-82-9
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: JLJKQBCOYKRMFV-BBVRLYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3R)-3-[(1S)-1-hydroxyethyl]-2-methyloxirane-2-carboxylate 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.33h， 生成 (4S,5S)-dihydro-4-hydroxy-5-methyl-3-methylene-furan-2(3H)-one
  参考文献：
  名称：

  Highly Stereoselective Epoxidation of α-Methyl-γ-hydroxy-α,β-unsaturated Esters:  Rationalization and Synthetic Applications

  摘要：

  The diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha, beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.

  DOI：

  10.1021/jo0709955
• 作为产物：
  描述：

  ethyl 4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-2-enoate 在 六甲基磷酰三胺 、 二叔丁基过氧化物 、 四丁基氟化铵 、 乙基锂 作用下， 以 四氢呋喃 、 环己烷 、 苯 为溶剂， 反应 176.0h， 生成 ethyl (2S,3R)-3-[(1S)-1-hydroxyethyl]-2-methyloxirane-2-carboxylate
  参考文献：
  名称：

  Highly Stereoselective Epoxidation of α-Methyl-γ-hydroxy-α,β-unsaturated Esters:  Rationalization and Synthetic Applications

  摘要：

  The diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha, beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.

  DOI：

  10.1021/jo0709955

文献信息

• Highly Stereoselective Epoxidation of α-Methyl-γ-hydroxy-α,β-unsaturated Esters:  Rationalization and Synthetic Applications
  作者：Irakusne López、Santiago Rodríguez、Javier Izquierdo、Florenci V. González

  DOI：10.1021/jo0709955

  日期：2007.8.1

  The diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha, beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.