N'-but-3-en-2-ylidenehydrazono-2,4,6-tri-isopropylphenylbenzenesulphonohydrazide | 84531-05-5

• 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: N'-but-3-en-2-ylidenehydrazono-2,4,6-tri-isopropylphenylbenzenesulphonohydrazide
• 英文别名: methyl vinyl ketone N-(2,4,6-tri-isopropylbenzene)sulfonyl hydrazone；2,4,6-tri-isopropylbenzenesulphonyl ('trisyl') hydrazone
• CAS: 84531-05-5
• 化学式: C₁₉H₃₀N₂O₂S
• 分子量: 350.525
• InChiKey: QSONPRIMFDQPQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxaldehyde 、 N'-but-3-en-2-ylidenehydrazono-2,4,6-tri-isopropylphenylbenzenesulphonohydrazide 以56%的产率得到(2RS,3RS,5RS)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-2-(1-methylene-2-propen-1-yl)cyclopentanecarboxaldehyde
  参考文献：
  名称：

  Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms

  摘要：

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.

  DOI：

  10.1021/jo702635t
• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰基肼 、 丁烯酮 反应 0.25h， 生成 N'-but-3-en-2-ylidenehydrazono-2,4,6-tri-isopropylphenylbenzenesulphonohydrazide
  参考文献：
  名称：

  2-lithio-1,3-丁二烯的生成及其与醛的反应

  摘要：

  Shapiro反应生成了2-Lithio-1,3-丁二烯。它与多种醛反应生成2-取代的丁二烯。

  DOI：

  10.1016/s0040-4039(00)88670-0

文献信息

• The generation of 2-lithio-1,3-butadiene and its reaction with aldehydes
  作者：Paul A. Brown、Paul R. Jenkin

  DOI：10.1016/s0040-4039(00)88670-0

  日期：1982.1

  2-Lithio-1,3-butadiene has been generated by the Shapiro reaction. It reacts with a range of aldehydes to give 2-substituted butadienes.

  Shapiro反应生成了2-Lithio-1,3-丁二烯。它与多种醛反应生成2-取代的丁二烯。
• Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms
  作者：Derrick L. J. Clive、Dazhan Liu

  DOI：10.1021/jo702635t

  日期：2008.4.1

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.