3--(E)-2-propen-1-ol | 137571-44-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3--(E)-2-propen-1-ol
• 英文别名: (2R,3S)-5-[3-[(E)-3-hydroxyprop-1-enyl]phenyl]-3-methylpentan-2-ol
• CAS: 137571-44-9
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: GRNJZQTYEHTKCA-KVOPJGFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3--(E)-2-propen-1-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 4 A molecular sieve 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-3-[3-((3S,4R)-4-Hydroxy-3-methyl-pentyl)-phenyl]-propane-1,2-diol
  参考文献：
  名称：

  Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit

  摘要：

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).

  DOI：

  10.1021/jo00029a033
• 作为产物：
  描述：

  3-甲基苯甲酸甲酯 在 manganese(IV) oxide 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 正丁基锂 、 过氧化氢苯甲酰 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 双氧水 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 氯仿 、 苯 为溶剂， 反应 9.33h， 生成 3--(E)-2-propen-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit

  摘要：

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).

  DOI：

  10.1021/jo00029a033

文献信息

• Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit
  作者：Mark A. Holoboski、Emil Koft

  DOI：10.1021/jo00029a033

  日期：1992.1

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).