2-氧代-5,6,7,8-四氢-2H-色满-3-羧酸乙酯 | 66979-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-氧代-5,6,7,8-四氢-2H-色满-3-羧酸乙酯
• 英文名称: ethyl 2-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-3-carboxylate
• 英文别名: 2-oxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxylic acid ethyl ester；Ethyl 2-oxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxylate；ethyl 2-oxo-5,6,7,8-tetrahydrochromene-3-carboxylate
• CAS: 66979-47-3
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD27952715
• 分子量: 222.241
• InChiKey: PSCJOBZZERBIBG-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±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
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存放在室温、干燥且密封的环境中。

反应信息

• 作为反应物：
  描述：

  2-氧代-5,6,7,8-四氢-2H-色满-3-羧酸乙酯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 36.0h， 生成 5,6,7,8-tetrahydro-1-hydroxy-3-naphthoic acid
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series

  摘要：

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.

  DOI：

  10.1021/jm000355t
• 作为产物：
  描述：

  环己酮 、 乙氧基甲叉丙二酸二乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以50%的产率得到2-氧代-5,6,7,8-四氢-2H-色满-3-羧酸乙酯
  参考文献：
  名称：

  WO2008/95058

  摘要：

  公开号：

文献信息

• Discovery of AMP Mimetics that Exhibit High Inhibitory Potency and Specificity for AMP Deaminase
  作者：Mark D. Erion、Srinivas Rao Kasibhatla、Brett C. Bookser、Paul D. van Poelje、M. Rami Reddy、Harry E. Gruber、James R. Appleman

  DOI：10.1021/ja983153j

  日期：1999.1.1

  The first potent, specific, and cell-penetrable AMP deaminase (AMPDA) inhibitors were discovered through an investigation of 3-substituted 3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol analogues. Inhibition constants for the most potent inhibitors were 105-fold lower than the KM for the substrate AMP. High affinity required the presence of both the 8-hydroxyl and the 3-substituent and is postulated

  通过对 3-取代 3,6,7,8-四氢咪唑并[4,5-d][1,3]diazepin-8-的研究，发现了第一个有效、特异性和细胞可渗透的 AMP 脱氨酶 (AMPDA) 抑制剂ol 类似物。最有效抑制剂的抑制常数比底物 AMP 的 KM 低 105 倍。高亲和力需要 8-羟基和 3-取代基的存在，并且被假定来自于降低结合熵成本并使二氮杂碱基采用模拟过渡态 (TS) 结构的结合构象的协同相互作用. 相对于其他 AMP 结合酶，AMPDA 抑制剂系列的高特异性 (> 105）部分归因于二氮杂碱，它有利于与用于稳定 TS 结构的残基相互作用，并排除通常由 AMP 结合酶用于结合 AMP 的相互作用。相比之下，AMPDA 和腺苷脱氨酶 (ADA) 之间的区别，这两种酶假定稳定类似的 TS 结构......
• Novel Skeleton Transformation Reaction of α-Pyrone Derivatives to Spirobicyclo[3.1.0]hexane Derivatives Using Dimethylsulfoxonium Methylide
  作者：Takuya Miura、Navnath Dnyanoba Yadav、Hiroki Iwasaki、Minoru Ozeki、Naoto Kojima、Masayuki Yamashita

  DOI：10.1021/ol302942m

  日期：2012.12.7

  transformation reaction using dimethylsulfoxonium methylide, a novel reaction was identified by which 5,6,7,8-tetrahydrocoumarin with the electron-withdrawing group at C3 was led to the spirobicyclo[3.1.0]hexane-cyclohexane derivative. Moreover, by establishing the scope of this reaction, it was confirmed that it is possible to apply this reaction to not only ring-fused α-pyrone derivatives but also a

  通过应用使用二甲基亚砜基的亚甲基进行的骨架转化反应，鉴定出一种新的反应，该反应通过将在C3处具有吸电子基团的5,6,7,8-四氢香豆素生成螺双环[3.1.0]己烷-环己烷衍生物。此外，通过确定该反应的范围，已证实不仅可以以中等至良好的产率将该反应应用于环稠合的α-吡喃酮衍生物，而且还可以应用于烷基链取代的α-吡喃酮衍生物。
• HCV PROTEASE INHIBITORS
  申请人：Yang Syaulan

  公开号：US20080207528A1

  公开（公告）日：2008-08-28

  This invention relates to the compounds of formula (I) shown below. Each variable in formula (I) is defined in the specification. These compounds can be used to treat hepatitis C virus infection.

  本发明涉及以下式子（I）的化合物。公式（I）中的每个变量在说明书中有定义。这些化合物可用于治疗丙型肝炎病毒感染。
• Diels-Alder reactions of 2-[(trialkylsilyl)oxy]pyrylium cations of 2H-pyran-2-one and 2H-1-benzopyran-2-one derivatives
  作者：Katsuo Ohkata、Yong Gyun Lee、Yukinori Utsumi、Kenji Ishimaru、Kinya Akiba

  DOI：10.1021/jo00017a014

  日期：1991.8

  The reactions of 6-methyl-2H-pyran-2-one and 2H-1-benzopyran-2-one with the 2-(trialkylsilyl)oxy dienes 6a-d in the presence of tert-butyldimethylsilyl triflate gave the [4 + 2] cycloadducts 7a-c and 8a-d regio- and stereoselectively in moderate yields. The ring junction in the cycloadducts is cis. The stereochemistry of 8a-d is discussed in terms of the H-1 NMR spectra of the compounds. Similar reactions of 3-(ethoxycarbonyl)-2-pyrones and 3-(alkoxycarbonyl)coumarins with the 2-(trialkylsilyl)oxy dienes 6a-e gave the cycloadducts 14-18 in satisfactory yields. Dehydrogenation of 7c, 8b, and 8c with DDQ in refluxing toluene afforded 23-25, respectively.
• [EN] HCV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTÉASE DU VIRUS DE L'HÉPATITE C
  申请人：TAIGEN BIOTECHNOLOGY CO LTD

  公开号：WO2008095058A1

  公开（公告）日：2008-08-07

  [EN] This invention relates to the compounds of formula (I) shown below. Each variable in formula (I) is defined in the specification. These compounds can be used to treat hepatitis C virus infection.
  [FR] La présente invention concerne des composés de formule (I), dans laquelle chaque variable est défini dans la description. Ces composés peuvent être utilisés pour traiter une infection du virus de l'hépatite C.