spiro[4.4]nonan-1-one tosylhydrazone | 736-85-6

• 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: spiro[4.4]nonan-1-one tosylhydrazone
• 英文别名: Spiro<4.4>nonan-1-on-；Spiro<4.4>nonan-1-on-p-tosylhydrazon；Spiro[4.4]nonan-1-on-(toluol-4-sulfonyl-hydrazon)；4-Methyl-N'-(spiro[4.4]nonan-1-ylidene)benzene-1-sulfonohydrazide；4-methyl-N-(spiro[4.4]nonan-4-ylideneamino)benzenesulfonamide
• CAS: 736-85-6
• 化学式: C₁₆H₂₂N₂O₂S
• 分子量: 306.429
• InChiKey: PVIJXDKJYKIWIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  spiro[4.4]nonan-1-one tosylhydrazone 在 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 1-bromo-spiro[4.4]non-1-ene
  参考文献：
  名称：

  Helical primary structures of 1,2-spiroannelated five-membered rings: attempted synthesis of (±)-tetraspiro[4.0.0.0.4.3.3.3]heneicosane

  摘要：

  A beta-hydroxy ketone with a helical carbon skeleton of five 1,2-spiroannelated cyclopentane rings is the main product of a Lewis acid catalyzed rearrangement of suitable sized alpha-hydroxy epoxides followed by an in situ equilibration via retro aldol reactions. Various attempts of a conversion to the title hydrocarbon failed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.073
• 作为产物：
  描述：

  spiro[4.4]nonan-1-one 、 对甲苯磺酰肼 以 甲醇 为溶剂， 反应 94.0h， 生成 spiro[4.4]nonan-1-one tosylhydrazone
  参考文献：
  名称：

  Helical primary structures of 1,2-spiroannelated five-membered rings: attempted synthesis of (±)-tetraspiro[4.0.0.0.4.3.3.3]heneicosane

  摘要：

  A beta-hydroxy ketone with a helical carbon skeleton of five 1,2-spiroannelated cyclopentane rings is the main product of a Lewis acid catalyzed rearrangement of suitable sized alpha-hydroxy epoxides followed by an in situ equilibration via retro aldol reactions. Various attempts of a conversion to the title hydrocarbon failed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.073

文献信息

• Helical primary structures of 1,2-spiroannelated five-membered rings: attempted synthesis of (±)-tetraspiro[4.0.0.0.4.3.3.3]heneicosane
  作者：Tien Widjaja、Lutz Fitjer、Kathrin Meindl、Regine Herbst-Irmer

  DOI：10.1016/j.tet.2008.02.073

  日期：2008.5

  A beta-hydroxy ketone with a helical carbon skeleton of five 1,2-spiroannelated cyclopentane rings is the main product of a Lewis acid catalyzed rearrangement of suitable sized alpha-hydroxy epoxides followed by an in situ equilibration via retro aldol reactions. Various attempts of a conversion to the title hydrocarbon failed. (c) 2008 Elsevier Ltd. All rights reserved.