(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one | 1352492-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one
• 英文别名: (5S)-6-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-1-phenylhex-1-yn-3-one
• CAS: 1352492-31-9
• 化学式: C₂₈H₃₀O₃Si
• 分子量: 442.63
• InChiKey: GYZWEUZOXWZLMC-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 palladium 10% on activated carbon 、 氢气 、 silver trifluoromethanesulfonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.75h， 生成 (2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate
  参考文献：
  名称：

  Stereoselective synthesis of a tetrahydropyranyl diarylheptanoid, ent-diospongin A

  摘要：

  The stereoselective synthesis of the unnatural enantiomer of a cyclic diarylheptanoid, diospongin A is described. The salient feature of this synthesis is the formation of a tetrahydropyran ring via the AgOTf-catalysed intramolecular oxa-Michael addition of a beta-hydroxy ynone followed by hydrogenation (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.006
• 作为产物：
  描述：

  苯乙炔 、 4-(tert-butyldiphenylsilanyloxy)-(3S)-hydroxy-N-methoxy-N-methylbutyramide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.0h， 以74%的产率得到(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one
  参考文献：
  名称：

  Stereoselective synthesis of a tetrahydropyranyl diarylheptanoid, ent-diospongin A

  摘要：

  The stereoselective synthesis of the unnatural enantiomer of a cyclic diarylheptanoid, diospongin A is described. The salient feature of this synthesis is the formation of a tetrahydropyran ring via the AgOTf-catalysed intramolecular oxa-Michael addition of a beta-hydroxy ynone followed by hydrogenation (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.006

文献信息

• Stereoselective synthesis of a tetrahydropyranyl diarylheptanoid, ent-diospongin A
  作者：Chada Raji Reddy、Guvvala Balakrishna Reddy、Boinapally Srikanth

  DOI：10.1016/j.tetasy.2011.10.006

  日期：2011.10

  The stereoselective synthesis of the unnatural enantiomer of a cyclic diarylheptanoid, diospongin A is described. The salient feature of this synthesis is the formation of a tetrahydropyran ring via the AgOTf-catalysed intramolecular oxa-Michael addition of a beta-hydroxy ynone followed by hydrogenation (C) 2011 Elsevier Ltd. All rights reserved.