2,3-dihydro-2-methylbenzofuran-4-carboxylic acid | 1261963-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-2-methylbenzofuran-4-carboxylic acid
• 英文别名: 2-Methyl-2,3-dihydro-1-benzofuran-4-carboxylic acid
• CAS: 1261963-74-9
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: ANPLWMFQFPHIRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-methylbenzofuran-4-carboxylic acid 在 氯化亚砜 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 N'-tert-butyl-N-2,3-dihydro-2-methylbenzofuran-4-carbohydrazide
  参考文献：
  名称：

  Synthesis, Crystal Structures, Insecticidal Activities, and Structure−Activity Relationships of Novel N′-tert-Butyl-N′-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide Derivatives

  摘要：

  Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine)carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by H-1 NMR spectra, HAMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N'-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.

  DOI：

  10.1021/jf104196t
• 作为产物：
  描述：

  methyl 3-(prop-2-ynyloxy)benzoate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 cesium fluoride 、 N,N-二乙基苯胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 20.0 ℃ 、7.09 MPa 条件下， 反应 35.0h， 生成 2,3-dihydro-2-methylbenzofuran-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, Crystal Structures, Insecticidal Activities, and Structure−Activity Relationships of Novel N′-tert-Butyl-N′-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide Derivatives

  摘要：

  Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine)carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by H-1 NMR spectra, HAMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N'-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.

  DOI：

  10.1021/jf104196t

文献信息

• METHOD FOR THE SYNTHESIS OF 4-BENZOFURAN-CARBOXYLIC ACID
  申请人：Burgos Alain

  公开号：US20090131688A1

  公开（公告）日：2009-05-21

  The invention concerns a novel method for synthesis of 4-benzofuran-carboxylic acid or alkyl ester thereof. This method is characterized in that a reaction for aromatization of a compound of formula (II) is performed for the synthesis of the compound of formula (I), according to the scheme A2 below: wherein R independently represents hydrogen or a linear or branched C 1 - 15 alkyl group. With the invention, it is possible to industrially synthesize 4-benzofuran-carboxylic acid or alkyl ester thereof with good yield and very good purity.

  该发明涉及一种合成4-苯并呋喃羧酸或其烷基酯的新方法。该方法的特点在于，根据下面的方案A2，对式（II）化合物进行芳香化反应以合成式（I）的化合物：其中R独立表示氢或直链或支链的C1-15烷基基团。通过这项发明，可以以良好的产率和非常高的纯度工业化合成4-苯并呋喃羧酸或其烷基酯。
• 3-AZA-BICYCLO[3.3.0]OCTANE COMPOUNDS
  申请人：Aissaoui Hamed

  公开号：US20100184808A1

  公开（公告）日：2010-07-22

  The invention relates to 3-aza-bicyclo[3.3.0]octane derivatives of the formula (I) wherein R 1 , R 2 , R 3 , and A are as described in the description and their use as orexin receptor antagonists.

  本发明涉及3-aza-bicyclo [3.3.0]辛烷衍生物，其化学式为(I)，其中R1，R2，R3和A如说明书所述，并将其用作促进醒觉素受体拮抗剂。
• Synthesis, Crystal Structures, Insecticidal Activities, and Structure−Activity Relationships of Novel <i>N</i>′-<i>tert</i>-Butyl-<i>N</i>′-substituted-benzoyl-<i>N</i>-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide Derivatives
  作者：Zhiqiang Huang、Yuxiu Liu、Yongqiang Li、Lixia Xiong、Zhipeng Cui、Hongjian Song、Hongli Liu、Qiqi Zhao、Qingmin Wang

  DOI：10.1021/jf104196t

  日期：2011.1.26

  Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N[di(octa)hydro]benzofuran(2,3-dihydro)benzo[1,3]([1,4])dioxine)carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by H-1 NMR spectra, HAMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N'-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.