meso-1-methylene-2,3-bis(propoxymethyl)cyclopropane | 1384245-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: meso-1-methylene-2,3-bis(propoxymethyl)cyclopropane
• 英文别名: (2S,3R)-1-methylidene-2,3-bis(propoxymethyl)cyclopropane
• CAS: 1384245-85-5
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: SXWQQLUZJSOTNA-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  meso-1-methylene-2,3-bis(propoxymethyl)cyclopropane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.0h， 生成 (3S,4R)-4-(methyldiphenylsilyl)-5-propoxy-3-(propoxymethyl)pentan-2-one
  参考文献：
  名称：

  Enhanced Catalyst Activity and Enantioselectivity with Chirality-Switchable Polymer Ligand PQXphos in Pd-Catalyzed Asymmetric Silaborative Cleavage of meso-Methylenecyclopropanes

  摘要：

  The poly(quinoxaline-2,3-diyl)-based helically chiral phosphine ligands PQXphos exhibited high enantioselectivities up to 97% ee in palladium-catalyzed desymmetrization of meso-1,2-dialkylsubstituted-3-methylenecyclopropanes through silaborative cleavage of the C C bond. The observed enantioselectivities were higher than those obtained with 2-diarylphosphino-1,1'-binaphthyl in our original report. Remarkable rate enhancement was also observed with a series of PQXphos in comparison with the corresponding low-molecular weight ligands.

  DOI：

  10.1021/ja303506k
• 作为产物：
  描述：

  4,4-dimethyl-8-methylene-3,5-dioxabicyclo[5.1.0]octane 在 盐酸 、 水 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 meso-1-methylene-2,3-bis(propoxymethyl)cyclopropane
  参考文献：
  名称：

  Enhanced Catalyst Activity and Enantioselectivity with Chirality-Switchable Polymer Ligand PQXphos in Pd-Catalyzed Asymmetric Silaborative Cleavage of meso-Methylenecyclopropanes

  摘要：

  The poly(quinoxaline-2,3-diyl)-based helically chiral phosphine ligands PQXphos exhibited high enantioselectivities up to 97% ee in palladium-catalyzed desymmetrization of meso-1,2-dialkylsubstituted-3-methylenecyclopropanes through silaborative cleavage of the C C bond. The observed enantioselectivities were higher than those obtained with 2-diarylphosphino-1,1'-binaphthyl in our original report. Remarkable rate enhancement was also observed with a series of PQXphos in comparison with the corresponding low-molecular weight ligands.

  DOI：

  10.1021/ja303506k