7-Benzo[1,3]dioxol-5-yl-heptanal | 93826-98-3

• 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: 7-Benzo[1,3]dioxol-5-yl-heptanal
• 英文别名: 1,3-Benzodioxole-5-heptanal；7-(1,3-benzodioxol-5-yl)heptanal
• CAS: 93826-98-3
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: DMFOETKYWSSQBU-UHFFFAOYSA-N

物化性质

• 沸点：
  118-120 °C(Press: 5-7 Torr)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Benzo[1,3]dioxol-5-yl-heptanal 在 氢氧化钾 、 sodium hydride 作用下， 反应 0.67h， 生成 (2E)-9-(3',4'-methylenedioxyphenyl)-2-nonenoic 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 palladium on activated charcoal lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， -65.0~65.0 ℃ 、255.1 kPa 条件下， 反应 8.0h， 生成 7-Benzo[1,3]dioxol-5-yl-heptanal
  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

• Synthesis of malabaricones, diarylnonanoids occurring in myristicaceous plants.
  作者：Yoshisuke TSUDA、Shinzo HOSOI、Yorii GOTO

  DOI：10.1248/cpb.39.18

  日期：——

  Naturally occurring diarylnonanoids, malabaricones A, B, C, D, and 1-(2-hydroxy-6-methoxyphenyl)-9-(3, 4-methylenedioxyphenyl)-nonan-1-one were synthesized from a common intermediate, 6-benzyloxyhexyltriphenyl phosphonium bromide, by use of the Witting reaction and crossed aldol reaction as key steps.

  自然界存在的二芳基壬烷类化合物，马拉巴酮A、B、C、D和1-(2-羟基-6-甲氧基苯基)-9-(3,4-亚甲二氧苯基)-壬烷-1-酮，通过共同的中间体6-苄氧基己基三苯基膦溴化物，利用Witting反应和交叉羟醛反应作为关键步骤合成。
• Total Synthesis of 3-<i>epi</i>-Juruenolide C
  作者：Noriki Kutsumura、Mai Inagaki、Akito Kiriseko、Takao Saito

  DOI：10.1248/cpb.c19-00209

  日期：2019.6.1

  In this study, the total synthesis of 3-epi-juruenolide C is achieved in 10 steps (longest linear sequence) starting from ethyl (2E,4S,5S)-4,5-dihydroxy-2-hexenoate. The synthetic highlights of our approach include one-pot regioselective bromination, intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel, and face-selective hydrogenation using a homogeneous Wilkinson's catalyst

  在这项研究中，从（2E，4S，5S）-4,5-二羟基-2-己酸乙酯开始的10个步骤（最长的线性序列）实现了3-epi-juruenolide C的总合成。我们方法的合成亮点包括一锅区域选择性溴化，使用双（三苯基膦）二羰基镍的分子内羰基化以及使用均相威尔金森氏催化剂的表面选择性氢化。
• Insecticidal amides. Synthesis of natural 2(),4(),10()-pipercide, its 2(), 4(), 10 ()- stereomer, and related isobutylamides
  作者：Leslie Crombie、Raynond Denman

  DOI：10.1016/s0040-4039(01)81413-1

  日期：1984.1

  Natural [ ()]pipercide and its 2(),4(),10()- stereomer are synthesised, the latter having superior insecticidal potency and knock down. 10,11-Dihydro- and 10,11-dehydropipercides are also prepared.

  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。
• Synthesis of (+)-Juruenolide C:  Use of Sequential 5-<i>Exo</i>-<i>Digonal</i> Radical Cyclization, 1,5-Intramolecular Hydrogen Transfer, and 5-<i>Endo</i>-<i>Trigonal</i> Cyclization
  作者：Derrick L. J. Clive、Elena-Simona Ardelean

  DOI：10.1021/jo010206y

  日期：2001.7.1

  Ph3SnH, the latter underwent 5-exo-digonal radical cyclization, intramolecular hydrogen transfer, and 5-endo-trigonal cyclization, yielding 15. Conversion of the lactone into the lactol benzyl ether 17, carbon-silicon bond cleavage, and regeneration of the lactone carbonyl gave (+)-juruenolide C (1).

  乙炔醇10依次转化为硅烷11和碳酸苯硒酯14。用Ph3SnH处理后，后者进行了5-外-对-自由基自由基环化，分子内氢转移和5-内-三角环化，得到15。内酯转化为内酯苄基醚17，碳-硅键断裂，内酯羰基再生，得到（+）-柔柔烯内酯C（1）。
• 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：——