(3S,5R)-2,4-Dimethyl-4,5-tridecadien-3-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,5R)-2,4-Dimethyl-4,5-tridecadien-3-ol
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: BLTXIGZINZRKMD-CVRLYYSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,5R)-2,4-Dimethyl-4,5-tridecadien-3-ol 在 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以78%的产率得到(2S,5R)-2-Isopropyl-3-methyl-5-heptyl-2,5-dihydrofuran
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of allenylcarbinols through SE2' addition of transient nonracemic propargylic stannanes to aldehydes.

  摘要：

  The nonracemic allenylstannane 1c was prepared by S(N)2' displacement of mesylate 8 with Bu(3)-SnLi-CuBr . SMe(2). Treatment of this stannane with BuSnCl(3) followed by addition of isobutyraldehyde at -40 degrees C afforded the syn allenylcarbinol 4c in nearly 80% yield, The nonracemic aldehydes (S)- and (R)-16 were similarly converted to the adducts 17 and 18 in high yield with good to excellent diastereoselectivity. Best results were obtained when hexane was employed as the solvent, A reaction pathway is proposed to account for the steric preference of these additions, The allenylcarbinols were converted stereospecifically to the cis-2,5-dihydrofurans 23-25 upon treatment with catalytic AgNO3 in acetone.

  DOI：

  10.1021/jo00122a040
• 作为产物：
  描述：

  2-Undecyn-4-ol 在 正丁基锂 、 sodium hydride 、 戴斯-马丁氧化剂 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 12.33h， 生成 (3S,5R)-2,4-Dimethyl-4,5-tridecadien-3-ol
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of allenylcarbinols through SE2' addition of transient nonracemic propargylic stannanes to aldehydes.

  摘要：

  The nonracemic allenylstannane 1c was prepared by S(N)2' displacement of mesylate 8 with Bu(3)-SnLi-CuBr . SMe(2). Treatment of this stannane with BuSnCl(3) followed by addition of isobutyraldehyde at -40 degrees C afforded the syn allenylcarbinol 4c in nearly 80% yield, The nonracemic aldehydes (S)- and (R)-16 were similarly converted to the adducts 17 and 18 in high yield with good to excellent diastereoselectivity. Best results were obtained when hexane was employed as the solvent, A reaction pathway is proposed to account for the steric preference of these additions, The allenylcarbinols were converted stereospecifically to the cis-2,5-dihydrofurans 23-25 upon treatment with catalytic AgNO3 in acetone.

  DOI：

  10.1021/jo00122a040

文献信息

• Diastereo- and enantioselective synthesis of allenylcarbinols through SE2' addition of transient nonracemic propargylic stannanes to aldehydes.
  作者：James A. Marshall、Richard H. Yu、Jolyon F. Perkins

  DOI：10.1021/jo00122a040

  日期：1995.9

  The nonracemic allenylstannane 1c was prepared by S(N)2' displacement of mesylate 8 with Bu(3)-SnLi-CuBr . SMe(2). Treatment of this stannane with BuSnCl(3) followed by addition of isobutyraldehyde at -40 degrees C afforded the syn allenylcarbinol 4c in nearly 80% yield, The nonracemic aldehydes (S)- and (R)-16 were similarly converted to the adducts 17 and 18 in high yield with good to excellent diastereoselectivity. Best results were obtained when hexane was employed as the solvent, A reaction pathway is proposed to account for the steric preference of these additions, The allenylcarbinols were converted stereospecifically to the cis-2,5-dihydrofurans 23-25 upon treatment with catalytic AgNO3 in acetone.