Cumaron-essigsaeure-(2)-chlorid | 86790-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Cumaron-essigsaeure-(2)-chlorid
• 英文别名: 2-benzofurylacetylchloride；3-Benzofuranacetylchloride；2-(1-benzofuran-2-yl)acetyl chloride
• CAS: 86790-43-4
• 化学式: C₁₀H₇ClO₂
• 分子量: 194.617
• InChiKey: ZKVGHBXQEGVOFH-UHFFFAOYSA-N

物化性质

• 沸点：
  150-155 °C(Press: 19 Torr)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Cumaron-essigsaeure-(2)-chlorid 在 dirhodium tetraacetate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 2-(2-methylbenzofuran-3-yl)acetate
  参考文献：
  名称：

  Intramolecular Carbenoid Insertions:  Reactions of α-Diazo Ketones Derived from Furanyl-, Thienyl-, (Benzofuranyl)-, and (Benzothienyl)acetic Acids with Rhodium(II) Acetate

  摘要：

  alpha-Diazo ketones tethered to furan, benzofuran, thiophene, and benzothiophene by a single methylene spacer have been shown to undergo atypical, rhodium(II) acetate catalyzed chemistry. For example, while treatment of 1-diazo-3-(3-furanyl)-2-propanone with Rh-2(OAc)(4) resulted in the expected 2-(4-oxo-2-cyclopentenylidene)acetaldehyde, isomeric 1-diazo-3-(2-furanyl)-2-propanone undergoes a vinylogous Wolff rearrangement and in the presence of water gives a mixture of 6a-methyl-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-one and 2-(2-methyl-3-furyl)acetic acid. Rhodium acetate catalyzed decomposition of 1-diazo-3-(3-benzofuranyl)-2-propanone and 1-diazo-3-(2-benzofuranyl)-2-propanone are also shown to undergo vinylogous Wolff rearrangement despite the fact that this chemistry is not observed with homologous benzofuranyl systems. alpha-Diazo ketones derived from benzothienyl propionic acids undergo the expected cyclization with 1-diazo-4-(3-benzothienyl)-2-butanone and 1-diazo-4-(2-benzothienyl)-2-butanone giving rise to 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-3-one and 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-2-one, respectively. While decomposition of 1-diazo-3-(3-benzothienyl)-2-propanone resulted in the formation of 2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-a-one, the isomeric 1-diazo-3-(2-benzothienyl)-2-propanone gave a dimer which resulted from a [3 + 2] cycloaddition followed by a [1,3]-alkyl shift. Overall, the results from this study of intramolecular carbenoid insertion into five-membered heteroaromatic systems show that the resultant chemistry is dependent on the nature of the heteroatom, position of substitution, and the length of the aliphatic tether.

  DOI：

  10.1021/jo9814593
• 作为产物：
  描述：

  2-苯并呋喃乙酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Cumaron-essigsaeure-(2)-chlorid
  参考文献：
  名称：

  Intramolecular Carbenoid Insertions:  Reactions of α-Diazo Ketones Derived from Furanyl-, Thienyl-, (Benzofuranyl)-, and (Benzothienyl)acetic Acids with Rhodium(II) Acetate

  摘要：

  alpha-Diazo ketones tethered to furan, benzofuran, thiophene, and benzothiophene by a single methylene spacer have been shown to undergo atypical, rhodium(II) acetate catalyzed chemistry. For example, while treatment of 1-diazo-3-(3-furanyl)-2-propanone with Rh-2(OAc)(4) resulted in the expected 2-(4-oxo-2-cyclopentenylidene)acetaldehyde, isomeric 1-diazo-3-(2-furanyl)-2-propanone undergoes a vinylogous Wolff rearrangement and in the presence of water gives a mixture of 6a-methyl-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-one and 2-(2-methyl-3-furyl)acetic acid. Rhodium acetate catalyzed decomposition of 1-diazo-3-(3-benzofuranyl)-2-propanone and 1-diazo-3-(2-benzofuranyl)-2-propanone are also shown to undergo vinylogous Wolff rearrangement despite the fact that this chemistry is not observed with homologous benzofuranyl systems. alpha-Diazo ketones derived from benzothienyl propionic acids undergo the expected cyclization with 1-diazo-4-(3-benzothienyl)-2-butanone and 1-diazo-4-(2-benzothienyl)-2-butanone giving rise to 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-3-one and 1,2,3,4-tetrahydrodibenzo[b,d]thiophen-2-one, respectively. While decomposition of 1-diazo-3-(3-benzothienyl)-2-propanone resulted in the formation of 2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-a-one, the isomeric 1-diazo-3-(2-benzothienyl)-2-propanone gave a dimer which resulted from a [3 + 2] cycloaddition followed by a [1,3]-alkyl shift. Overall, the results from this study of intramolecular carbenoid insertion into five-membered heteroaromatic systems show that the resultant chemistry is dependent on the nature of the heteroatom, position of substitution, and the length of the aliphatic tether.

  DOI：

  10.1021/jo9814593

文献信息

• N-substituted 3-aryl piperidines and derivatives thereof
  申请人：BEECHAM GROUP PLC

  公开号：EP0077607A1

  公开（公告）日：1983-04-27

  Compounds of the formula (I), and pharmaceutically acceptable salts thereof: wherein: R, is hydroxy, C1-4 alkoxy or an in-vivo hydrolysable acyloxy group: R2 is hydrogen, C1-4 alkyl, hydroxy, C1-4 alkoxy or an in-vivo hydrolysable acyloxy group; R4 is benzofuryl, benzothienyl, indolyl, quinolyl, isoquinolyl,2,3-dihydrobenzofuryl, 2,3-dihydrobenzylthienyl or 2,3-dihydroindolyl optionally substituted by one or two substituents selected from C1-4 alkoxy, hydroxy or acyloxy, trifluoromethyl, halogen or nitro; and A is a bond or C1-6 alkylene, a process for their preparation, and pharmaceutical compositions containing them.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 R，是羟基、C1-4 烷氧基或体内可水解的酰氧基： R2 是氢、C1-4 烷基、羟基、C1-4 烷氧基或体内可水解的酰氧基； R4 是苯并呋喃基、苯并噻吩基、吲哚基、喹啉基、异喹啉基、2,3-二氢苯并呋喃基、2,3-二氢苄基噻吩基或 2,3-二氢吲哚基，可任选被选自 C1-4 烷氧基、羟基或酰氧基、三氟甲基、卤素或硝基的一个或两个取代基取代；以及 A 是键或 C1-6 烷基、 它们的制备方法，以及含有它们的药物组合物。
• AMINOCYCLOHEXYLESTERS AND USES THEREOF
  申请人：UNIVERSITY OF BRITISH COLUMBIA

  公开号：EP0720605B1

  公开（公告）日：2001-12-19
• US4460594A
  申请人：——

  公开号：US4460594A

  公开（公告）日：1984-07-17
• US5637583A
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  公开号：US5637583A

  公开（公告）日：1997-06-10
• US5885984A
  申请人：——

  公开号：US5885984A

  公开（公告）日：1999-03-23