ethyl 8-methoxy-2-oxo-2H-cycloheptafuran-3-carboxylate | 1025-12-3

• 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-methoxy-2-oxo-2H-cycloheptafuran-3-carboxylate
• 英文别名: ethyl 8-metoxy-2-oxo-2H-cycloheptafuran-3-carboxylate；8-methoxy-3-ethoxycarbonyl-2H-cycloheptafuran-2-one；8-methoxy-2-oxo-2H-cyclohepta[b]furan-3-carboxylic acid ethyl ester；3-Aethoxycarbonyl-8-methoxy-1-oxa-azulan-2-on；2H-Cyclohepta[b]furan-3-carboxylic acid, 8-methoxy-2-oxo-, ethyl ester；ethyl 8-methoxy-2-oxocyclohepta[b]furan-3-carboxylate
• CAS: 1025-12-3
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: DOTJTYBYSQDQSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  ethyl 8-methoxy-2-oxo-2H-cycloheptafuran-3-carboxylate 在 吗啉 、 磷酸 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 1-hexyl-8-methoxyazulene
  参考文献：
  名称：

  Synthesis and anti-ulcer activities of sodium alkylazulene sulfonates.

  摘要：

  多种新合成的钠代烷基吖啶磺酸盐衍生物在沙伊幽门结扎大鼠中进行了其抗溃疡活性的检测。此外，还研究了这些新吖啶衍生物的亲脂性（log P）这一物理化学参数，以探讨结构-活性关系。log P的最佳值，即提供最大抗溃疡活性的值，大约为-1.0。在检测的吖啶衍生物中，3-乙基-7-异丙基吖啶-1-磺酸钠盐（KT1-32）对沙伊溃疡显示出极其强大的抑制作用，其抗胃酸活性比愈创木基吖啶磺酸钠（GAS）更强。此外，与GAS相比，KT1-32在加热过程中极为稳定。

  DOI：

  10.1248/cpb.36.641
• 作为产物：
  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

文献信息

• Synthesis of a Polycyclic π-Conjugated System Containing an Azulene Unit by the Flash Vacuum Pyrolytic Method. III. Synthesis and Properties of 4-Hydroxy-3<i>H</i>-cyclopent[<i>a</i>]azulen-3-one
  作者：Yoichiro Kitamori、Masafumi Yasunami、Takanori Hioki、Kahei Takase、Masaaki Yoshifuji

  DOI：10.1246/bcsj.65.3282

  日期：1992.12

  4-Hydroxy-3H-cyclopent[a]azulen-3-one, a new tricyclic π-conjugated system containing a hydroxyazulene unit and a cyclopentadienone moiety, was synthesized by the application of flash vacuum pyrolysis in the final step. All the proton magnetic resonances of the compound shifted up-field compared with those of the referenced 1,2-dihydro compound in terms of an induced paramagnetic ring current in the periphery of this molecule. The characteristic prototropic tautomerization of 4-hydroxyazulenes was not observed in this system.

  一种新型三环π共轭体系化合物4-羟基-3H-环戊[a]氮杂卓-3-酮，包含一个羟基氮杂卓单元和一个环戊二烯酮部分，其最终通过闪速真空热解法合成。与参考的1,2-二氢化合物相比，该化合物所有质子的核磁共振谱线均向上场偏移，表明分子外围存在诱导的顺磁性环流。该体系并未观察到4-羟基氮杂卓的典型质子转移互变异构现象。
• Design, synthesis, and pharmacology of 3-substituted sodium azulene-1-sulfontes and related compounds: non-prostanoid thromboxane A2 receptor antagonists
  作者：Tsuyoshi Tomiyama、Masayuki Yokota、Shuichi Wakabayashi、Kazuhiro Kosakai、Takashi Yanagisawa

  DOI：10.1021/jm00059a001

  日期：1993.4

  series of novel azulene-1 carboxylic acid derivatives 28-30, azulene-1 sulfonic acid sodium salts 41a-c, and related compounds were synthesized. These compounds were tested for TXA2 receptor antagonistic activity. The inhibitory concentrations (IC50) of these compounds for vascular contraction (TXA2 tau receptor) and platelet aggregation (TXA2 alpha receptor) induced by (15S)-15-hydroxy-11 alpha,9

  合成了一系列新颖的a1羧酸衍生物28-30，-11磺酸钠盐41a-c和相关化合物。测试这些化合物的TXA2受体拮抗活性。这些化合物对（15S）-15-羟基-11 alpha，9 alpha-（epoxymethano）prosta-5（Z）诱导的血管收缩（TXA2 tau受体）和血小板聚集（TXA2 alpha受体）的抑制浓度（IC50）获得了13，（E）-二烯酸（U-46619）。Azulene-1-磺酸钠盐41a-c的效力是Azulene-1-羧酸28-30的3倍以上。最有效的化合物41b在抑制血管收缩（tau受体）方面比TXA2拮抗剂BM13,177强4个数量级，IC50为9.0 x 10（-10）M. 还发现化合物41b是tau受体选择性拮抗剂（收缩的IC50 /聚集的IC50 = 378），在浓度高达10（-4）M时没有TXA2合成酶抑制活性，在浓度高达10（-4）M时没有部分激
• 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。
• 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
• Synthesis of 2-Amino-1-cyanoazulenes: Substituent Effect on 2H-Cyclohepta[b]furan-2-ones toward the Reaction with Malononitrile
  作者：Taku Shoji、Shuhei Sugiyama、Kota Miura、Akira Ohta、Ryuta Sekiguchi、Shunji Ito、Shigeki Mori

  DOI：10.3987/com-18-s(t)89

  日期：——

  3-Substituted 2-amino- 1-cyanoazulene derivatives were prepared by the reaction of 2H-cyclohepta[b]furan-2-ones with malononitrile in the presence of triethylamine as a base. The great influence of the substituent at their 3-position on the reactivity to form the 2-aminoazulene derivatives was revealed. The intramolecular charge transfer (ICT) characters of 2-amino- 1-cyano-3-vinylazulenes were investigated by UV/Vis spectroscopy and theoretical calculations. The structure of compounds 13b and 14b was clarified by single crystal X-ray analysis.