ethyl 8-hydroxy-2-oxo-2H-cycloheptafuran-3-carboxylate | 2222-19-7

• 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 8-hydroxy-2-oxo-2H-cycloheptafuran-3-carboxylate
• 英文别名: ethyl 8-hydroxy-2-oxocyclohepta[b]furan-3-carboxylate
• CAS: 2222-19-7
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: YIHRZRYKGKUCBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.74
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 8-hydroxy-2-oxo-2H-cycloheptafuran-3-carboxylate 生成 ethyl 8-hydroxy-2-oxo-3,3a,4,5,6,7,8,8a-octahydrocyclohepta[b]furan-3-carboxylate
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-oxo-2H-cyclohepta[b]furan-3-carboxylate 在 盐酸 作用下， 以75%的产率得到ethyl 8-hydroxy-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

文献信息

• 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。
• The Synthesis of 8-Hydroxy-1-oxaazulan-2-one and Its Derivatives by the Condensation of 3-Bromotropolones with Diethyl Malonate and Ethyl Acetoacetate
  作者：Kahei Takase

  DOI：10.1246/bcsj.37.1460

  日期：1964.10
• Tropolone derivatives as synthetic intermediates. 1. A novel synthetic method of the octahydro-2H-cyclohepta[b]furan-2-one derivatives
  作者：Masayoshi Ando、Naoki Kataoka、Masafumi Yasunami、Kahei Takase、Naonori Hirata、Yoshikazu Yanagi

  DOI：10.1021/jo00384a010

  日期：1987.4
• Nozoe, Tetsuo; Wakabayashi, Hidetsugu; Ishikawa, Sumio, Heterocycles, 1990, vol. 31, # 1, p. 17 - 22
  作者：Nozoe, Tetsuo、Wakabayashi, Hidetsugu、Ishikawa, Sumio、Wu, Chi-Phi、Yang, Paw-Wang

  DOI：——

  日期：——
• Nozoe, Tetsuo; Wakabayashi, Hidetsugu; Shindo, Kimio, Heterocycles, 1991, vol. 32, # 2, p. 213 - 220
  作者：Nozoe, Tetsuo、Wakabayashi, Hidetsugu、Shindo, Kimio、Ishikawa, Sumio、Wu, Chi-Phi、Yang, Paw-Wang

  DOI：——

  日期：——