7-Benzo[1,3]dioxol-5-yl-heptanoic acid methyl ester | 214462-84-7

• 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: 7-Benzo[1,3]dioxol-5-yl-heptanoic acid methyl ester
• 英文别名: Methyl 7-(1,3-benzodioxol-5-yl)heptanoate
• CAS: 214462-84-7
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: UOSRYGJYIQHEOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Benzo[1,3]dioxol-5-yl-heptanoic acid methyl ester 在 氢氧化钾 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 7.08h， 生成 11-(3',4'-methylenedioxyphenyl)-undeca-2(E),4(E)-dienoic acid
  参考文献：
  名称：

  A Practical and Efficient Synthetic Route to Dihydropipercide and Pipercide¹

  摘要：

  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.

  DOI：

  10.1021/jo981039d
• 作为产物：
  描述：

  6-氧代己酸甲酯 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 甲醇 、 正己烷 、 苯 为溶剂， 20.0 ℃ 、255.1 kPa 条件下， 反应 3.0h， 生成 7-Benzo[1,3]dioxol-5-yl-heptanoic acid methyl ester
  参考文献：
  名称：

  A Practical and Efficient Synthetic Route to Dihydropipercide and Pipercide¹

  摘要：

  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.

  DOI：

  10.1021/jo981039d

文献信息

• AROMATIC ALKENOIC ACID DERIVATIVES
  申请人：Symrise AG

  公开号：US20150259319A1

  公开（公告）日：2015-09-17

  What are proposed are primarily aromatic alkenoic acid derivatives of the formula I for use in a therapeutic method as (a) means for reducing appetite and/or (b) means for causing a feeling of satiation and/or as (c) means for reducing energy intake and/or as (d) mood enhancers, and the non-therapeutic use of the aromatic alkenoic acid derivatives of formula I as (a) means for reducing appetite and/or (b) means for causing a feeling of satiation and/or as (c) means for reducing energy intake and/or as (d) mood enhancers.
• 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.