7-(3',4'-methylenedioxyphenyl)-6(E)-heptenol | 75335-50-1

• 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-(3',4'-methylenedioxyphenyl)-6(E)-heptenol
• 英文别名: (E)-7-(1,3-benzodioxol-5-yl)hept-6-en-1-ol
• CAS: 75335-50-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: DUFUXVJFHXUWTE-GQCTYLIASA-N

物化性质

• 熔点：
  40.0-41.5 °C
• 沸点：
  152-155 °C(Press: 6-7 Torr)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-(3',4'-methylenedioxyphenyl)-6(E)-heptenol 在 氢氧化钾 、 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 反应 0.17h， 生成 (2E,8E)-9-(3',4'-methylenedioxyphenyl)-2,8-nonadienoic acid
  参考文献：
  名称：

  在犬第二代幼虫中与哌酰胺有关的芳烷基和芳烯基酰胺的合成和杀线活性。

  摘要：

  合成了与哌啶相关的79个芳烷基和芳烯基酰胺，并研究了它们对犬round虫Toxocara canis的第二级幼虫的杀线虫活性。活性很大程度上取决于烷基链的长度和胺部分的性质，但是几乎不受链中是否存在双键的影响。在一系列同系物中表现出最强活性的烷基链长，对于吡咯烷酰胺为m = 11，对于N-甲基哌嗪酰胺为m = 13。尽管在所测试的同系物中，哌啶（3，4-亚甲基二氧苯基同系物）显示出最强的活性，但是芳环上的甲氧基取代基对该活性没有太大影响。然而，甲氧基向羟基的转化大大降低了活性并缩短了链长，从而提供了最强的活性。计算出的非酚芳基哌啶的log P值在3.5至4.5范围内，而羟苯基哌啶的log P值较小，表明酚和非酚化合物的杀线活性涉及不同的机理。

  DOI：

  10.1248/cpb.45.685
• 作为产物：
  描述：

  6-氧代己酸甲酯 在 lithium aluminium tetrahydride 、 正丁基锂 、 air 、 苯硫酚 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 3.33h， 生成 7-(3',4'-methylenedioxyphenyl)-6(E)-heptenol
  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

• Structural and synthetic studies on the retrofractamides—amide constituents of Piper retrofractum
  作者：Avijit Banerji、Debabrata Bandyopadhyay、Manjusha Sarkar、Arup K. Siddhanta、Sudhir C. Pal、Somnath Ghosh、Koshy Abraham、James N. Shoolery

  DOI：10.1016/s0031-9422(00)83537-2

  日期：1985.2

  C, were isolated from the total above-ground parts of Piper retrofractum . Retrofractamide A was shown to be N -isobutyl-9(3′,4′-methylenedioxyphenyl)2 E ,4 E ,8 E -nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and

  摘要 从Piper retrofractum 的全部地上部分分离得到两种新的不饱和酰胺，retrofractamides A 和C。光谱和化学研究表明 Retrofractamide A 是 N-isobutyl-9(3',4'-methylenedioxyphenyl)2 E,4 E,8 E-nonatrienamide。反曲霉胺 C 的结构 6 是从光谱和化学研究中提出的，并通过全立体选择性合成得到证实。芝麻素和3,4,5-三甲氧基二氢肉桂酸以及retrofractamide A 的两个高级同系物的存在，即。证明了哌啶（retrofractamide B）和retrofractamide D。也实现了哌啶的合成。
• Concise, efficient new synthesis of pipercide, an insecticidal unsaturated amide from Piper nigrum, and related compounds
  作者：George M. Strunz、Heather Finlay

  DOI：10.1016/s0040-4020(01)89414-x

  日期：1994.1

  Pipercide and piperolein A, unsaturated amides from Piper nigrum, were prepared in overall yields of 21% and 35% respectively, by a new, short and efficient strategy, in which the key step was the aldol-Grob-type fragmentation sequence recently reported by Sakai et al.. (but using propylene- rather than ethylene glycol). The nor-homologues of these natural products were similarly prepared. In the final

  通过新的，短而有效的策略，分别从Piper nigrum制备了总产率分别为21％和35％的Pipercide和Piperolein A（不饱和酰胺），其中的关键步骤是最近报道的aldol-Grob型片段化序列。 Sakai等人（但使用丙二醇而不是乙二醇）。这些天然产物的非同源物以类似方式制备。在最后的步骤中，可以通过Roskamp的方法（包括用Sn [N（TMS）2 ] 2和适当的胺处理）直接从酯中制备酰胺，或者通过常规方法从相应的羧酸中制备酰胺。
• 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：——
• Crude Drugs Effective on Visceral Larva Migrans. Part XVIII. Synthesis and Nematocidal Activity of Aralkyl- and Aralkenylamides Related to Piperamide on Second-Stage Larvae of Toxocara canis.
  作者：Fumiyuki KIUCHI、Norio NAKAMURA、Makiko SAITOH、Kazue KOMAGOME、Hirokuni HIRAMATSU、Noriaki TAKIMOTO、Nobuaki AKAO、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.45.685

  日期：——

  piperamides (3,4-methylenedioxyphenyl homologues) showed the strongest activity among the homologues tested, methoxy substituent(s) on the aromatic ring did not have much effect on the activity. However, conversion of the methoxy group to a hydroxy group greatly decreased the activity and shortened the chain length giving the strongest activity. Calculated log P values of non-phenolic aryl-piperamides fell

  合成了与哌啶相关的79个芳烷基和芳烯基酰胺，并研究了它们对犬round虫Toxocara canis的第二级幼虫的杀线虫活性。活性很大程度上取决于烷基链的长度和胺部分的性质，但是几乎不受链中是否存在双键的影响。在一系列同系物中表现出最强活性的烷基链长，对于吡咯烷酰胺为m = 11，对于N-甲基哌嗪酰胺为m = 13。尽管在所测试的同系物中，哌啶（3，4-亚甲基二氧苯基同系物）显示出最强的活性，但是芳环上的甲氧基取代基对该活性没有太大影响。然而，甲氧基向羟基的转化大大降低了活性并缩短了链长，从而提供了最强的活性。计算出的非酚芳基哌啶的log P值在3.5至4.5范围内，而羟苯基哌啶的log P值较小，表明酚和非酚化合物的杀线活性涉及不同的机理。