dimethyl (1S*,2S*,3S*)-4-methylene-3-(methylthio)-3-(trimethylsilyl)cyclobutane-1,2-dicarboxylate | 132118-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: dimethyl (1S*,2S*,3S*)-4-methylene-3-(methylthio)-3-(trimethylsilyl)cyclobutane-1,2-dicarboxylate
• 英文别名: dimethyl (1R,2S,3R)-4-methylidene-3-methylsulfanyl-3-trimethylsilylcyclobutane-1,2-dicarboxylate
• CAS: 132118-85-5；132200-74-9
• 化学式: C₁₃H₂₂O₄SSi
• 分子量: 302.467
• InChiKey: JOMDYLZRFHDILK-OUJBWJOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-methylthio-1-trimethylsilyl-1,2-propadiene 、 富马酸二甲酯 、 二氯乙基铝 生成 dimethyl (1S*,2S*,3S*)-4-methylene-3-(methylthio)-3-(trimethylsilyl)cyclobutane-1,2-dicarboxylate
  参考文献：
  名称：

  HAYASHI, YUJIRO;NIIHATA, SHIGEO;NARASAKA, KOICHI, CHEM. LETT.,(1990) N1, C. 2091-2094

  摘要：

  DOI：

文献信息

• [2+2] Cycloaddition Reaction between Allenyl Sulfides and Electron Deficient Olefins Promoted by Lewis Acids
  作者：Yujiro Hayashi、Shigeo Niihata、Koichi Narasaka

  DOI：10.1246/cl.1990.2091

  日期：1990.11

  Methylenecyclobutane derivatives are prepared by the Lewis acid promoted [2+2] cycloaddition reactions of 1-substituted-1-methylthio-1,2-propadienes and electron deficient olefms. The asymmetric [2+2] cycloaddition of the allenyl sulfides also proceeds in high enantioselectivity by the use of a chiral titanium reagent.

  通过路易斯酸促进的 1-取代-1-甲硫基-1,2-丙二烯和缺电子烯烃的 [2+2] 环加成反应，制备出亚甲基环丁烷衍生物。通过使用手性钛试剂，还能以较高的对映选择性进行烯基硫化物的不对称 [2+2] 环加成反应。
• Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent
  作者：Koichi Narasaka、Yujiro Hayashi、Hideshi Shimadzu、Shigeo Niihata

  DOI：10.1021/ja00049a020

  日期：1992.11

  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.