methyl 6-isopropyl-2-oxo-2H-cycloheptafuran-3-carboxylate | 106021-18-5

• 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: methyl 6-isopropyl-2-oxo-2H-cycloheptafuran-3-carboxylate
• 英文别名: 6-isopropyl-3-(methoxycarbonyl)-2H-cycloheptafuran-2-one；(4Z,6Z,8E)-methyl 6-isopropyl-2-oxo-2H-cyclohepta[b]furan-3-carboxylate；methyl 2-oxo-6-propan-2-ylcyclohepta[b]furan-3-carboxylate
• CAS: 106021-18-5
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: AIUSVDWWUJHIOV-UHFFFAOYSA-N

物化性质

• 沸点：
  470.8±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  methyl 6-isopropyl-2-oxo-2H-cycloheptafuran-3-carboxylate 在 吗啉 、 吡啶 、 三氯化铝 、 磷酸 、 sodium methylate 、 三氧化硫吡啶 、 sodium hydride 、 苯甲醚 作用下， 生成 钠3-[4-[(4-氯苯基)磺酰基氨基]丁基]-6-丙-2-基薁e-1-磺酸酯
  参考文献：
  名称：

  Azulene衍生物：新型非前列腺素血栓烷A2受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00171a004
• 作为产物：
  描述：

  2-chloro-4-isopropyltropone 、 丙二酸二甲酯 在 甲醇 、 sodium methylate 作用下， 生成 methyl 6-isopropyl-2-oxo-2H-cycloheptafuran-3-carboxylate
  参考文献：
  名称：

  Sato, Tohoku Daigaku Hisui Yoeki Kagaku Kenkyusho Hokoku, 1959, vol. 8, p. 47,62

  摘要：

  DOI：

文献信息

• 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
• Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2<i>H</i>-cyclohepta[<i>b</i>]furan-2-ones with silyl enol ethers
  作者：Taku Shoji、Shuhei Sugiyama、Yoshiaki Kobayashi、Akari Yamazaki、Yukino Ariga、Ryuzi Katoh、Hiroki Wakui、Masafumi Yasunami、Shunji Ito

  DOI：10.1039/c9cc09376a

  日期：——

  We developed a procedure for the direct synthesis of 2-arylazulenes, which were obtained in moderate to excellent yields, by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with aryl-substituted silyl enol ethers. The structures of some 2-arylazulenes were clarified by single-crystal X-ray analysis. The 2-phenylazulene derivatives obtained by this study showed noticeable fluorescence in acidic

  我们开发了一种直接合成2-芳基azulenes的程序，该方法可以通过2H-环庚[b]呋喃-2-酮与芳基取代的甲硅烷基烯醇醚的[8 + 2]环加成反应而以中等至极好的收率获得。通过单晶X射线分析澄清了一些2-芳基az嗪的结构。通过该研究获得的2-苯基氮杂烯衍生物在酸性介质中显示出明显的荧光。
• Superjacent and Subjacent Orbitals Participations for Kinetically-Controlled Cycloaddition Reactions of 2<i>H</i>-Cyclohepta[<i>b</i>]furan-2-ones and 8,8-Dicyanoheptafulvene to 2,3-Bis(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptadiene
  作者：Guan Rong Tian、Shigeru Sugiyama、Akira Mori、Hitoshi Takeshita、Miwako Higashi、Hiroyuki Yamaguchi

  DOI：10.1246/bcsj.62.1136

  日期：1989.4.15

  2.1]heptadiene with 2H-cyclohepta[b]furan-2-ones and 8,8-dicyanoheptafulvene gave [4+2]adducts exclusively. This mode is different from the reported [8+2]adduct formations for 2H-cyclohepta[b]furan-2-ones with enamines and alkoxyethenes. A consideration of the superjacent and subjacent orbitals effects of the MO calculations gave a better result in favor of [4+2]adduct formation. Thermolysis of cycloadducts

  2,3-双(甲氧基羰基)-7-氧杂双环[2.2.1]庚二烯与2H-环庚[b]呋喃-2-酮和8,8-二氰基七富烯的热环加成反应仅得到[4+2]加合物。这种模式与报道的 2H-环庚 [b]furan-2-ones 与烯胺和烷氧基乙烯的 [8+2] 加合物形成不同。考虑到 MO 计算的上层和下层轨道效应，可以得到更好的结果，有利于 [4+2] 加合物的形成。环加合物的热解得到高巴瑞烯的亚甲基衍生物。
• Studies on anti-ulcer agents. II. Synthesis and anti-ulcer activities of 6-isopropylazulene-1-sodium sulfonate derivatives.
  作者：Takashi YANAGISAWA、Kazuhiro KOSAKAI、Tsuyoshi TOMIYAMA、Masafumi YASUNAMI、Kahei TAKASE

  DOI：10.1248/cpb.38.3355

  日期：——

  A series of alkylazulene-1-sodium sulfonate derivatives which has an isopropyl group at 6-position were synthesized, and their anti-ulcer activities were examined in Shay pylorus-ligated rats. The values of lipophilicity (log P) as a parameter of these new azulene derivatives were also examined in reference to the structure-activity relationship. The optimum value of log P, which showed maximal anti-ulcer activity, was about -0.46. Among the derivatives of azulene examined, 3-ethyl-6-isopropylazulene-1-sodium sulfonate (compound IXb : KT1-785) exhibited the most potent inhibitory action against Shay ulcer, and its anti-peptic activity was similar to that of 3-ethyl-7-isopropylazulene-1-sodium sulfonate (KT1-32). It also had more activity than guaiazulene sodium sulfonate (GAS). Furthermore, KT1-785 was extremely stable under heating as compared to GAS.

  研究人员合成了一系列烷基氮杂环烯-1-磺酸钠衍生物，这些衍生物在 6 位上有一个异丙基，并在 Shay 幽门结扎大鼠体内检测了它们的抗溃疡活性。此外，还参照结构-活性关系研究了这些新的薁衍生物的亲脂性（log P）参数值。显示最大抗溃疡活性的最佳对数值约为-0.46。在所研究的薁衍生物中，3-乙基-6-异丙基薁-1-磺酸钠（化合物 IXb：KT1-785）对夏伊溃疡的抑制作用最强，其抗消化活性与 3-乙基-7-异丙基薁-1-磺酸钠（KT1-32）相似。它的活性也高于瓜亚磺酸钠（GAS）。此外，与 GAS 相比，KT1-785 在加热条件下极为稳定。
• Synthesis, stability and bonding situation of tris-, bis- and mono[9-(azuleno[1,2-b]thienyl)]methyl cationsElectronic supplementary information (ESI) available: CV waves of compounds 7a, 8a and 9a, redox details of compounds 7a,b, 8a,b, and 9a,b along with those of 4a, 5a and 6a, ORTEP drawings and details of the X-ray analyses of compounds 2b and 9b and NMR details of the compounds reported. See http://www.rsc.org/suppdata/ob/b3/b302688d/
  作者：Shunji Ito、Takahiro Kubo、Mao Kondo、Chizuko Kabuto、Noboru Morita、Toyonobu Asao、Kunihide Fujimori、Masataka Watanabe、Nobuyuki Harada、Masafumi Yasunami

  DOI：10.1039/b302688d

  日期：——

  Stable tris-, bis- and mono[9-(azuleno[1,2-b]thienyl)]methyl cations (7a, 8a and 9a) and their derivatives, with a 6-isopropyl substituent on each azuleno[1,2-b]thiophene ring (7b, 8b and 9b) were prepared by the hydride abstraction reaction of the corresponding methane derivatives. The bonding situation of these compounds including the methane derivatives was examined by analysis of the 3J(H,H) values

  稳定的三，双和单[9-（azuleno [1,2-b]噻吩基）]甲基阳离子（7a，8a和9a）及其衍生物，在每个azuleno [1,2-]上均具有6-异丙基取代基b]噻吩环（7b，8b和9b）是通过相应的甲烷衍生物的氢化物提取反应制备的。通过从1H NMR光谱分析七元环的3J（H，H）值，检查了包括甲烷衍生物在内的这些化合物的键合情况。甲烷衍生物在3J（H，H）值中表现出明显的交替模式，这表明z并核的pi系统被稠合的噻吩环扰动，显示出向局部七氟甲醚亚结构的趋势。七元环中7b和8b的3J（H，H）值表明，z腈核中仍存在交替的CC键长。在七元环中表现出几乎相等的3J（H，H）值的阳离子9a和9b在z烯核中表现出离域的tropylium亚结构的发展。对6-异丙基azuleno [1,2-b]噻吩的X射线晶体分析表明，七元环中的键长交替较大。通过9b的X射线晶体分析也证实了七元环中的键长均等化。通过测量pKR