(3S,4S)-4-tert-Butyl-3-methyl-oxetan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S)-4-tert-Butyl-3-methyl-oxetan-2-one
• 英文别名: (3S,4S)-4-tert-butyl-3-methyloxetan-2-one
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: HDUPGKLMPBTASR-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 苯甲醛 、 (3S,4S)-4-tert-Butyl-3-methyl-oxetan-2-one 生成 (3R,4S)-4-tert-Butyl-3-methyl-3-((R)-phenyl-trimethylsilanyloxy-methyl)-oxetan-2-one
  参考文献：
  名称：

  Mulzer, Johann; Chucholowski, Alexander, Angewandte Chemie, 1982, vol. 94, # 10, p. 787 - 788

  摘要：

  DOI：
• 作为产物：
  描述：

  特戊醛 、 2-((Z)-1-Triethylsilanyloxy-propenylsulfanyl)-pyridine 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以5%的产率得到(3S,4S)-4-tert-Butyl-3-methyl-oxetan-2-one
  参考文献：
  名称：

  A Stereocomplementary Approach to β-Lactones:  Highly Diastereoselective Synthesis of cis-β-Lactones, a β-Chloro Acid, and a Tetrahydrofuran

  摘要：

  [GRAPHICS]In the course of mechanistic studies of the ZnCl2-mediated tandem Mukaiyama aldol-lactonization reaction of aldehydes and thiopyridyl ketene acetals, a stereocomplementary reaction employing SnCl4 was discovered. This method provides a highly diastereoselective entry to cis-1,2-disubstituted beta-lactones as well as a beta-chloro carboxylic acid and a tetrahydrofuran. The former products were obtained by varying the reaction temperature. The latter product was obtained when the aldehyde substrate bore a pendant silyl ether.

  DOI：

  10.1021/ol990860o

文献信息

• A Stereocomplementary Approach to β-Lactones:  Highly Diastereoselective Synthesis of <i>cis</i>-β-Lactones, a β-Chloro Acid, and a Tetrahydrofuran
  作者：Yingcai Wang、Cunxiang Zhao、Daniel Romo

  DOI：10.1021/ol990860o

  日期：1999.10.1

  [GRAPHICS]In the course of mechanistic studies of the ZnCl2-mediated tandem Mukaiyama aldol-lactonization reaction of aldehydes and thiopyridyl ketene acetals, a stereocomplementary reaction employing SnCl4 was discovered. This method provides a highly diastereoselective entry to cis-1,2-disubstituted beta-lactones as well as a beta-chloro carboxylic acid and a tetrahydrofuran. The former products were obtained by varying the reaction temperature. The latter product was obtained when the aldehyde substrate bore a pendant silyl ether.
• Mulzer, Johann; Chucholowski, Alexander, Angewandte Chemie, 1982, vol. 94, # 10, p. 787 - 788
  作者：Mulzer, Johann、Chucholowski, Alexander

  DOI：——

  日期：——