sesamyl β-cyanoethylether | 82872-97-7

• 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: sesamyl β-cyanoethylether
• 英文别名: 3-(benzo[1,3]dioxol-5-yloxy)-propionitrile；Propanenitrile, 3-(1,3-benzodioxol-5-yloxy)-；3-(1,3-benzodioxol-5-yloxy)propanenitrile
• CAS: 82872-97-7
• 化学式: C₁₀H₉NO₃
• mdl: MFCD11131684
• 分子量: 191.186
• InChiKey: FJFNNPPPAFZQOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sesamyl β-cyanoethylether 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 42.5h， 生成
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular C−O Bond Formation

  摘要：

  A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction. and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile,

  DOI：

  10.1021/ja012046d
• 作为产物：
  描述：

  芝麻酚 、 丙烯腈 在 potassium carbonate 作用下， 以 叔丁醇 为溶剂， 生成 sesamyl β-cyanoethylether
  参考文献：
  名称：

  通过钯（II）催化色胺酮与芳基硼酸的一锅β-芳基化反应合成黄酮。

  摘要：

  合宜地通过一锅二价的苯并二氢吡喃酮与芳基硼酸通过串联钯（II）催化合成了苯并二氢吡喃酮（一类具有化学未活化β位点的简单酮），合成了47种黄烷酮。该反应提供了一种以高达92％的收率获得各种黄烷酮（包括天然产物，如柚皮苷三甲醚）的新颖途径。

  DOI：

  10.1021/acs.joc.9b01162

文献信息

• Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists
  作者：Yukiyoshi Yamazaki、Kazutoyo Abe、Tsutomu Toma、Masahiro Nishikawa、Hidefumi Ozawa、Ayumu Okuda、Takaaki Araki、Soichi Oda、Keisuke Inoue、Kimiyuki Shibuya、Bart Staels、Jean-Charles Fruchart

  DOI：10.1016/j.bmcl.2007.05.066

  日期：2007.8

  A combination of benzoxazole, phenoxyalkyl side chain, and phenoxybutyric acids was identified as a highly potent and selective human peroxisome proliferator-activated receptor alpha (PPARalpha) agonist. The synthesis, structure-activity relationship (SAR) studies, and in vivo activities of the representative compounds are described.

  苯并恶唑，苯氧基烷基侧链和苯氧基丁酸的组合被确定为高度有效和选择性的人类过氧化物酶体增殖物激活受体α（PPARalpha）激动剂。描述了代表性化合物的合成，结构-活性关系（SAR）研究和体内活性。
• Synthesis, characterization, and antimicrobial activity of novel substituted 2H-chromenyl acrylates
  作者：N. J. P. Subhashini、M. Ravi、D. Cherupally、B. China Raju、E. V. Reddy、H. Bee

  DOI：10.1134/s1070363216120586

  日期：2016.12

  The present study deals with conventional Witting olefination of 2H-chromene-3-carbaldehydes with stabilized ylide in the presence of dichloromethane to afford (2E)-ethyl-3-(4-chloro-2H-chromen-3-yl) acrylate derivatives. All the products were found to have E-geometry at C=C bond. The synthesized compounds were characterized by spectral data such as IR, H-1 NMR and MS. Compounds were screened for antimicrobial activity against strains of gram positive, gram negative bacterial and fungal strains. All compounds showed good antibacterial and antifungal activity.
• Devakumar, C.; Saxena, V. S.; Mukerjee, S. K., Agricultural and Biological Chemistry, 1985, vol. 49, # 3, p. 725 - 730
  作者：Devakumar, C.、Saxena, V. S.、Mukerjee, S. K.

  DOI：——

  日期：——
• Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
  作者：Hyung-Seok Yoo、Seung Hwan Son、Yang Yil Cho、Soo Jin Lee、Hyu Jeong Jang、Young Min Kim、Dong Hwan Kim、Nam Yong Kim、Boyoung Y. Park、Yong Sup Lee、Nam-Jung Kim

  DOI：10.1021/acs.joc.9b01162

  日期：2019.8.16

  total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92%.

  合宜地通过一锅二价的苯并二氢吡喃酮与芳基硼酸通过串联钯（II）催化合成了苯并二氢吡喃酮（一类具有化学未活化β位点的简单酮），合成了47种黄烷酮。该反应提供了一种以高达92％的收率获得各种黄烷酮（包括天然产物，如柚皮苷三甲醚）的新颖途径。
• Palladium-Catalyzed Intramolecular C−O Bond Formation
  作者：Shin-itsu Kuwabe、Karen E. Torraca、Stephen L. Buchwald

  DOI：10.1021/ja012046d

  日期：2001.12.1

  A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction. and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile,