methyl 3-benzyl-4-methylene-3-(methylthio)-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate | 132118-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl 3-benzyl-4-methylene-3-(methylthio)-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate
• CAS: 132118-93-5；132200-76-1；145212-53-9；145212-61-9
• 化学式: C₁₉H₂₁NO₅S
• 分子量: 375.445
• InChiKey: GAQRJNBGJHVNQE-YCQNMSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3-benzyl-4-methylene-3-(methylthio)-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate 在 lithium aluminium tetrahydride 、 magnesium methanolate 作用下， 生成 ((1S,2R,4R)-2-Benzyl-4-hydroxymethyl-3-methylene-2-methylsulfanyl-cyclobutyl)-methanol 、 ((1R,2R,4S)-2-Benzyl-4-hydroxymethyl-3-methylene-2-methylsulfanyl-cyclobutyl)-methanol 、 ((1R,2S,4S)-2-Benzyl-4-hydroxymethyl-3-methylene-2-methylsulfanyl-cyclobutyl)-methanol
  参考文献：
  名称：

  Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent

  摘要：

  In the presence of certain Lewis acids, alkenes containing an alkylthio group (for example, ketene dithioacetals, alkenyl sulfides, alkynyl sulfides, and allenyl sulfides) react with electron deficient olefins to give the corresponding cyclobutane, cyclobutene, or methylene cyclobutane derivatives. By employing a chiral titanium catalyst generated in situ from dichlorodiisopropoxytitanium and a tartrate-derived chiral diol, the [2 + 2] cycloaddition reaction proceeds with high enantioselectivity.

  DOI：

  10.1021/ja00049a020
• 作为产物：
  描述：

  3-[(E)-3-(methoxycarbonyl)-propenoyl]-oxazolidin-2-one 、 3-(methylthio)-4-phenyl-1,2-butadiene 在 二异丙氧基二氯化钛 、 (+)-4,5-双[羟基(二苯基)甲基]-2-甲基-2-苯基-1,3-二氧戊环 作用下， 以 甲苯 、 Petroleum ether 为溶剂， 生成 methyl 3-benzyl-4-methylene-3-(methylthio)-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate
  参考文献：
  名称：

  Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent

  摘要：

  In the presence of certain Lewis acids, alkenes containing an alkylthio group (for example, ketene dithioacetals, alkenyl sulfides, alkynyl sulfides, and allenyl sulfides) react with electron deficient olefins to give the corresponding cyclobutane, cyclobutene, or methylene cyclobutane derivatives. By employing a chiral titanium catalyst generated in situ from dichlorodiisopropoxytitanium and a tartrate-derived chiral diol, the [2 + 2] cycloaddition reaction proceeds with high enantioselectivity.

  DOI：

  10.1021/ja00049a020