ethyl 2-oxo-2H-cyclohepta[b]furan-3-carboxylate | 22442-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: ethyl 2-oxo-2H-cyclohepta[b]furan-3-carboxylate
• 英文别名: 3-ethoxycarbonyl-2H-cyclohepta[b]furan-2-one；Ethyl 2-oxo-2H-cyclohepta(b)furan-3-carboxylate；ethyl 2-oxocyclohepta[b]furan-3-carboxylate
• CAS: 22442-46-2
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: JULPYSSLWYDUIT-UHFFFAOYSA-N

物化性质

• 沸点：
  479.3±28.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-oxo-2H-cyclohepta[b]furan-3-carboxylate 在 盐酸 、 sodium hydroxide 、 silver nitrate 作用下， 反应 8.0h， 生成 ethyl 8-methoxy-2-oxo-2H-cycloheptafuran-3-carboxylate
  参考文献：
  名称：

  Formation and structure of 2-diazo-2,4-azulenequinone derivatives

  摘要：

  The diazotization of methyl (and ethyl) 2-amino-3-cyano-4-methoxy(and ethoxy)azulene-1-carboxylate (1-4) was examined to determine whether the products are 2-diazo-2,4-azulenequinone derivatives (B) or azulene-2-diazonium-1-carboxylate derivatives (C). Since diazotization of 1 and 2 gave the same diazo compound 5 and diazotization of both 3 and 4-gave diazo compound 6, the diazo compounds are deduced to not be azulene-2-diazonium-1-carboxylate derivatives (7 and 8), but rather to be 2-diazo-2,4-azulenequinone derivatives (5 and 6). The diazo carbons of both 5 and 6 show C-13 NMR signals at delta 66.3, and their carbonyl carbons resonate at 6 181.1, in good agreement with a 2-diazo-2,4-azulenequinone structure. The structures of diazo compounds 24 and 25, which we have previously reported,(1) are reexamined on the basis of the analysis of their C-13 NMR spectra. The contribution of a quinoid structure and a diazoazulenolate structure to 5, 6, 24, and 25 is discussed by comparison of their C-13 NMR spectral data with those of 4-diazo-2,5-cyclohexadien-1-one derivatives. It is concluded that the contribution of the quinoid structure is larger than that of the diazoazulenolate structure.

  DOI：

  10.1021/jo00123a031
• 作为产物：
  描述：

  2-氯-2,4,6-环庚三烯-1-酮 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 33.5h， 生成 ethyl 2-oxo-2H-cyclohepta[b]furan-3-carboxylate
  参考文献：
  名称：

  （三苯基亚砷烷基）甲基环庚-2,4,6-三烯酮衍生物的合成，结构和反应性：杂多烯与活化乙炔的反应

  摘要：

  稳定的叶立德衍生物7a，b轴承环庚-2,4,6-三烯基和吸电子基团CO 2 Et和CN分别是通过与2-氯环庚-2,4,6-三烯酮在卜的存在相应的鉮甲基氧衍生物吨确定。化合物7a，b被分离为稳定的结晶化合物，不会经历水解即使在酸性条件下。X射线晶体分析表明，它们的As–O键距（7a为2.31Å，7b为2.39Å）低于范德华半径的总和（3.37Å），因此，砷和氧元素。为了构建一系列环庚环杂环并为了更好地理解一系列砷化钠，允许7a，b与二甲基碳杂杂环烯反应，异硫氰酸苯酯，二苯基碳二亚胺基和 异氰酸苯酯，在Wittig型反应中，随后进行电环化或正式的[8 + 2]型环加成消除 三苯ar硫醚 或者 氧化物 给 2 H-环庚[ b ]呋喃-2-硫酮， 它的 亚胺， 2-苯基亚氨基-2 H-环庚[ b ]吡咯， 和 2 H-环庚[ b ]呋喃-2-酮。另一方面，7a，b与乙炔二羧酸二甲酯 （DMAD）给

  DOI：

  10.1039/b205612g

文献信息

• [8+2] Cycloaddition Reactions of 2H-Cyclohepta[b]furan-2-one with Acyclic 1,3-Dienes: A Facile Route to Novel Bicyclo [5.3.0] ring Systems
  作者：Vijay Nair、G Anilkumar、M.V Nandakumar、Bini Mathew、Nigam P Rath

  DOI：10.1016/s0040-4039(97)01472-x

  日期：1997.9

  Novel [8+2] cycloaddition reactions of 3-ethoxy carbonyl 2H-cyclohepta[b]furan-2-one with acyclic 1,3-dienes are described. The potential application of this process in the synthesis of modified colchicinoids incorporating bicyclo [5.3.0] ring systems has also been studied. © 1997 Elsevier Science Ltd.

  描述了3-乙氧基羰基2H-环庚[b]呋喃-2-酮与无环1,3-二烯的新型[8 + 2]环加成反应。还研究了该方法在结合双环[5.3.0]环系统的修饰类秋水仙碱合成中的潜在应用。©1997爱思唯尔科学有限公司。
• Synthesis and Analysis of Positive Inotropic Effects of 3-Substituted-2H-cyclohepta(b)furan-2-one Derivatives.
  作者：Masayuki YOKOTA、Takashi YANAGISAWA、Kazuhiro KOSAKAI、Shuichi WAKABAYASHI、Tsuyoshi TOMIYAMA、Masafumi YASUNAMI

  DOI：10.1248/cpb.42.865

  日期：——

  Several 3-substituted-2H-cyclohepta[b]furan-2-one derivatives were prepared and tested in vitro for positive inotropic character. Introduction of an isopropyl group at the 5-position of compound 8a caused an increase of PIC50 (negative logarithm of the dosage which increases the contractile force by 50%) from 4.48 to 5.10. Among the 5-isopropyl-8-alkoxy compounds, the isopropoxy compound 12f had the most potent activity with a PIC50 value of 5.99. Conversion of the ester group at the 3-position to a methylene group and of the alkoxy group at the 8-position to a substituted amino group caused a decrease in activity. The most active compound, 12f, was also found to have a weaker heart rate (HR)-increasing effect compared to milrinone and amrinone.

  合成了几种3-取代的-2H-环庚[b]呋喃-2-酮衍生物，并在体外测试了它们的正性肌力特性。在化合物8a的5-位引入异丙基，使得PIC50值（增加收缩力50%的剂量的负对数）从4.48增加到5.10。在5-异丙基-8-烷氧基化合物中，异丙氧基化合物12f具有最强的活性，PIC50值为5.99。将3-位的酯基转换为亚甲基，将8-位的烷氧基转换为取代氨基，会导致活性降低。最活跃的化合物12f，与米力农和氨力农相比，对心率（HR）增加的影响较弱。
• Cycloaddition reactions of 2-oxo-2H-cyclohepta[b]furan derivatives with dienes and dienophiles
  作者：Vijay Nair、M.V. Nandakumar、G. Anilkumar、Guenter K. Eigendorf

  DOI：10.1016/s0040-4020(99)00100-3

  日期：1999.3

  Cycloaddition reactions of 2-oxo-2H-cyclohepta[b]furan derivatives participating as 8π and 4π components respectively towards different dienes and dienophiles are described. The observed reactivity and periselectivity have been rationalized by AM1 calculations.

  描述了分别以8π和4π组分参与的2-oxo-2H-cyclohepta [b]呋喃衍生物对不同的二烯和双亲物的环加成反应。观察到的反应性和选择性是通过AM1计算合理化的。
• The formation of azulene derivatives from 2H-cyclohepta[b]furan-2-one derivatives
  作者：T. Nozoe、K. Takase、T. Nakazawa、S. Fukuda

  DOI：10.1016/s0040-4020(01)97748-8

  日期：——

  ethoxide or t-butyl-amine, giving the corresponding 1,2,3-trisubstituted azulene derivatives, respectively. The structures of these azulene derivatives are determined on the basis of chemical evidence, and spectral data. Considering the structural correlation between the starting 2H-cyclohepta[b]furan-2-ones and the azulene derivatives obtained, a reasonable reaction course, involving the heptafulvene-type

  3-乙氧基羰基-和3-乙酰基-2 H-环庚[ b ]呋喃-2-酮易于与丙二腈反应。氰基乙酰胺，氰基乙酸乙酯和丙二酸二乙酯，在乙醇钠或叔丁胺的存在下，分别得到相应的1,2,3-三取代的z并衍生物。这些a菁衍生物的结构是根据化学证据和光谱数据确定的。考虑到起始的2 H-环庚[ b ]呋喃-2-酮与所获得的氮杂环戊烯衍生物之间的结构相关性，提出了一种合理的反应过程，涉及七富烯型和二氢氮杂环戊烷型中间体，可用于从中形成氮杂环戊烯衍生物。 2 H-环庚基[ b]呋喃-2-酮。
• Cycloaddition reactions of 2-oxo-2H-cyclohepta[b]furan derivatives with arylacetylenes and the di-π-methane rearrangement of homobarrelene derivatives
  作者：Vijay Nair、Mecheril Valsan Nandakumar、Gopinathan Nair Anilkumar、Davis Maliakal、Mariappanadar Vairamani、Sripadi Prabhakar、Nigam P. Rath

  DOI：10.1039/b005377p

  日期：——

  2-Oxo-2H-cyclohepta[b]furan derivatives participate in [4 + 2]cycloaddition reactions with aryl acetylenes leading to homobarrelene derivatives and the latter undergo di-π-methane rearrangement resulting in complex carbocycles.

  2- 氧代-2H-环庚烷并[b]呋喃衍生物与芳基乙炔发生[4Â +Â 2]环加成反应，生成同巴氏衍生物，后者发生二Ï-甲烷重排反应，生成复杂的碳环。

表征谱图