(S)-(+)-1-bromo-3-heptanol | 143617-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-1-bromo-3-heptanol
• 英文别名: (3S)-1-bromoheptan-3-ol
• CAS: 143617-68-9
• 化学式: C₇H₁₅BrO
• 分子量: 195.1
• InChiKey: AIXPPZKKRNGALD-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (S)-(+)-1-bromo-3-heptanol 在 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 乙腈 为溶剂， 反应 34.25h， 生成 rel-(2R,6R)-2-(3-hydroxyheptyl)-6-propylpiperidine
  参考文献：
  名称：

  Enantioselective ruthenium-mediated synthesis of (-)-indolizidine 223AB

  摘要：

  Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (-)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP.Ru*-mediated hydrogenation of the corresponding beta-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80-degrees-C and 50 psig of H-2.

  DOI：

  10.1021/jo00048a037
• 作为产物：
  描述：

  methyl (S)-3-hydroxyheptanoate 在 吡啶 、 lithium aluminium tetrahydride 、 三乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (S)-(+)-1-bromo-3-heptanol
  参考文献：
  名称：

  Enantioselective ruthenium-mediated synthesis of (-)-indolizidine 223AB

  摘要：

  Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (-)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP.Ru*-mediated hydrogenation of the corresponding beta-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80-degrees-C and 50 psig of H-2.

  DOI：

  10.1021/jo00048a037

文献信息

• Enantioselective ruthenium-mediated synthesis of (-)-indolizidine 223AB
  作者：Douglass F. Taber、P. Bruce Deker、Lee J. Silverberg

  DOI：10.1021/jo00048a037

  日期：1992.10

  Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (-)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP.Ru*-mediated hydrogenation of the corresponding beta-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80-degrees-C and 50 psig of H-2.