(4S,6E)-4,6-Dimethyl-6-nonen-3-one | 61090-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6E)-4,6-Dimethyl-6-nonen-3-one
• 英文别名: (E,4S)-4,6-dimethylnon-6-en-3-one
• CAS: 61090-97-9；83269-71-0；87758-53-0
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: VMIHRSFDMSRUGK-PCYYEKQGSA-N

物化性质

• 沸点：
  230.6±9.0 °C(Predicted)
• 密度：
  0.837±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-bromo-2-methyl-2-pentene 在 六甲基磷酰三胺 、 正丁基锂 、 samarium diiodide 、 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 23.67h， 生成 (4S,6E)-4,6-Dimethyl-6-nonen-3-one
  参考文献：
  名称：

  Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

  摘要：

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00617-0

文献信息

• Andersen, Marc W.; Hildebrandt, Bernhard; Hoffmann, Reinhard W., Angewandte Chemie, 1991, vol. 103, # 1, p. 90 - 92
  作者：Andersen, Marc W.、Hildebrandt, Bernhard、Hoffmann, Reinhard W.

  DOI：——

  日期：——
• Andersen, Marc W.; Hildebrandt, Bernhard; Dahmann, Georg, Chemische Berichte, 1991, vol. 124, # 9, p. 2127 - 2139
  作者：Andersen, Marc W.、Hildebrandt, Bernhard、Dahmann, Georg、Hoffmann, Reinhard W.

  DOI：——

  日期：——
• Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step
  作者：Jef De Brabander、Wolfgang Oppolzer

  DOI：10.1016/s0040-4020(97)00617-0

  日期：1997.7

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.