10,11-dihydroretrofractamide B | 75022-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 10,11-dihydroretrofractamide B
• 英文别名: Dihydroretrofractamide B；(2E,4E)-11-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4-dienamide
• CAS: 75022-26-3
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: DMIKQRDDTCGOLE-VTKKNFPDSA-N

物化性质

• 熔点：
  89.5-91.5 °C
• 沸点：
  548.8±50.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,6-己二醇 在 palladium on activated charcoal 氢氧化钾 、 草酰氯 、 氢溴酸 、 氢气 、 sodium ethanolate 、 氢气 、 magnesium 、 pyridinium chlorochromate 作用下， 以 甲醇 为溶剂， 生成 10,11-dihydroretrofractamide B
  参考文献：
  名称：

  杀虫酰胺。天然2（），4（），10（）-哌啶，其2（），4（），10（）-立体异构体和相关异丁酰胺的合成

  摘要：

  合成了天然的[ （）]哌啶及其2（），4（），10（）-立体异构体，后者具有优异的杀虫效力和击倒性。还制备了10，11-二氢和10，11-脱氢哌啶。

  DOI：

  10.1016/s0040-4039(01)81413-1

文献信息

• Miyakado, Masakazu; Nakayama, Isamu; Yoshioka, Hirosuke, Agricultural and Biological Chemistry, 1980, vol. 44, # 7, p. 1701 - 1704
  作者：Miyakado, Masakazu、Nakayama, Isamu、Yoshioka, Hirosuke

  DOI：——

  日期：——
• A Practical and Efficient Synthetic Route to Dihydropipercide and Pipercide¹
  作者：Lloyd W. Rotherham、J. Edward Semple

  DOI：10.1021/jo981039d

  日期：1998.9.1

  Dihydropipercide 1 and Pipercide 2 are examples of hydrophobic insecticidal isobutylamide derivatives isolated from Piper Nigrum L. which have received synthetic attention over the past decade. Novel structural features combining the N-isobutyldieneamide array, found in related natural products such as Pellitorine, with the 3,4-methylenedioxyphenyl moiety, found in insecticide synergists including Piperonyl Butoxide and Sesamex, render these as attractive targets for synthesis. Although a variety of synthetic routes to related natural products have appeared in the literature, practical methods for the preparation of the title compounds were lacking. Convenient and convergent 10-11-step protocols were developed which provided access to gram quantities of the targets. Methyl 6-oxohexanoate 4 was prepared from cyclohexanone enol acetate 3 via a tandem ozonolysis, methanolysis, hydrolysis process. Subsequent olefination and olefin isomerization steps followed by further elaboration provided the targets 1 and 2. Noteworthy features of this methodology include the convenient synthesis of oxoester intermediate 4 and the phenythio radical-induced olefin isomerization of intermediate 6 which afforded high yields of >99.5% E-olefin 13. These are both somewhat uncommon but potentially useful processes which may find further application in organic synthesis.
• Sabharwal; Dogra; Sharma, Journal of the Indian Chemical Society, 1990, vol. 67, # 4, p. 318 - 320
  作者：Sabharwal、Dogra、Sharma、Kalra、Vig、Kad

  DOI：——

  日期：——
• SABHARWAL, ARUN;DOGRA, VIJAV;SHARMA, SANJIV;KALRA, RAHMI;VIG, O. P.;KAD, +, J. INDIAN CHEM. SOC., 67,(1990) N, C. 318-320
  作者：SABHARWAL, ARUN、DOGRA, VIJAV、SHARMA, SANJIV、KALRA, RAHMI、VIG, O. P.、KAD, +

  DOI：——

  日期：——
• JPS5687505A
  申请人：——

  公开号：JPS5687505A

  公开（公告）日：1981-07-16