(S,S,S)-1-(3-(3-(benzyloxy)prop-1-ynyl)oxiran-2-yl)-ethanol | 1138138-99-4

• 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: (S,S,S)-1-(3-(3-(benzyloxy)prop-1-ynyl)oxiran-2-yl)-ethanol
• 英文别名: (1S)-1-[(2S,3S)-3-(3-phenylmethoxyprop-1-ynyl)oxiran-2-yl]ethanol
• CAS: 1138138-99-4
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: XTABAMCWGYJBGM-UBHSHLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S,S)-1-(3-(3-(benzyloxy)prop-1-ynyl)oxiran-2-yl)-ethanol 、 甲基氯化镁 在 亚磷酸三苯酯 、 氰化亚铜 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以93%的产率得到(2S,3R,5R(a))-7-(benzyloxy)-6-methylhepta-4,5-dien-2,3-diol
  参考文献：
  名称：

  Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine

  摘要：

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.104
• 作为产物：
  描述：

  (E)-7-(benzyloxy)hept-3-en-5-yn-2-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 336.0h， 以38%的产率得到(R,E)-7-(benzyloxy)hept-3-en-5-yn-2-ol
  参考文献：
  名称：

  Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine

  摘要：

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.104

文献信息

• Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine
  作者：Frank Volz、Sipke H. Wadman、Anja Hoffmann-Röder、Norbert Krause

  DOI：10.1016/j.tet.2008.11.104

  日期：2009.2

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.