(2S,3R,4R)-(+)-2-benzyloxy-4-methyl-5-hexyn-3-ol | 320716-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4R)-(+)-2-benzyloxy-4-methyl-5-hexyn-3-ol
• 英文别名: (2S,3R,4R)-4-methyl-2-phenylmethoxyhex-5-yn-3-ol
• CAS: 320716-52-7
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: VKCLCUBAIRCQQS-MBNYWOFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (2S,3R,4R)-(+)-2-benzyloxy-4-methyl-5-hexyn-3-ol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到(2S,3R,4R)-(+)-2,3-bis-benzyloxy-4-methyl-5-hexyne
  参考文献：
  名称：

  Additions of Enantioenriched Allenylzinc and Indium Reagents to Lactic Aldehyde Ethers

  摘要：

  Allenylzinc and indium reagents were generated in situ through Pd(0)-catalyzed metalation of (R)- and (S)-3-butyn-2-ol-methanesulfonate with Et2Zn ana InI. These reagents add to the benzyl and TBS ethers of(S)-lactic aldehyde to afford diastereomeric stereotriads in;moderate to high yield. The (S)/(S) combination afforded the anti,anti adducts with 94:6-100:0 diastereoselectivity. The (R)I(S) combination was mismatched, affording a mixture of anti,syn and syn,anti adducts in; diastereomeric ratios of ca. 80:20-85:15. Addition of the racemic allenylmetal reagents to the (S)lactic aldehyde ethers afforded the products of matched and mismatched pairings in equal amount.

  DOI：

  10.1021/jo005658+
• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 、 (S)-3-butyn-2-ol mesylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 indium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 3.0h， 以89%的产率得到(2S,3R,4R)-(+)-2-benzyloxy-4-methyl-5-hexyn-3-ol
  参考文献：
  名称：

  Additions of Enantioenriched Allenylzinc and Indium Reagents to Lactic Aldehyde Ethers

  摘要：

  Allenylzinc and indium reagents were generated in situ through Pd(0)-catalyzed metalation of (R)- and (S)-3-butyn-2-ol-methanesulfonate with Et2Zn ana InI. These reagents add to the benzyl and TBS ethers of(S)-lactic aldehyde to afford diastereomeric stereotriads in;moderate to high yield. The (S)/(S) combination afforded the anti,anti adducts with 94:6-100:0 diastereoselectivity. The (R)I(S) combination was mismatched, affording a mixture of anti,syn and syn,anti adducts in; diastereomeric ratios of ca. 80:20-85:15. Addition of the racemic allenylmetal reagents to the (S)lactic aldehyde ethers afforded the products of matched and mismatched pairings in equal amount.

  DOI：

  10.1021/jo005658+