5-(噻吩-2-基)戊酸甲酯 | 71877-34-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-(噻吩-2-基)戊酸甲酯
• 英文名称: 5-(thien-2-yl)valeric acid methyl ester
• 英文别名: methyl 5-(thien-2-yl)-valerate；5-[2]thienyl-valeric acid methyl ester；5-[2]Thienyl-valeriansaeure-methylester；Methyl 2-thiophenevalerate；methyl 5-thiophen-2-ylpentanoate
• CAS: 71877-34-4
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: GROUZPMPFVOVEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(噻吩-2-基)戊酸甲酯 在 吡啶 、 氢氧化钾 、 三氯化铝 、 草酰氯 、 氨 、 溴 、 一水合肼 作用下， 以 二硫化碳 、 乙二醇 为溶剂， 反应 0.5h， 生成 2,5-di(4-aminobutyl)thiophene
  参考文献：
  名称：

  Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain

  摘要：

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80070-1
• 作为产物：
  描述：

  戊二酸单甲酯 在 盐酸 、 氢氧化钾 、 氯化亚砜 、 四氯化锡 、 对甲苯磺酸 、 肼 作用下， 反应 24.0h， 生成 5-(噻吩-2-基)戊酸甲酯
  参考文献：
  名称：

  Wierzbicki, Michel; Boussard, Marie-Francoise; Sauveur, Frederic, Arzneimittel-Forschung/Drug Research, 1998, vol. 48, # 8, p. 840 - 849

  摘要：

  DOI：

文献信息

• Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis
  作者：Xiao-Biao Yan、Chun-Ling Li、Wen-Jie Jin、Peng Guo、Xing-Zhong Shu

  DOI：10.1039/c8sc00609a

  日期：——

  Coupling reactions involving non-sulfonated C–O electrophiles provide a promising method for forming C–C bonds, but the incorporation of functionalized or secondary alkyl groups remains a challenge due to the requirement for well-defined alkylmetal species. In this study, we report a reductive nickel-catalyzed cross-coupling of benzyl oxalates with alkyl bromides, using oxalate as a new leaving group

  涉及非磺化C-O亲电子试剂的偶联反应为形成C-C键提供了一种有前途的方法，但由于需要明确的烷基金属种类，官能化或仲烷基的掺入仍然是一个挑战。在这项研究中，我们报道了草酸苄酯与烷基溴的还原镍催化交叉偶联，使用草酸作为新的离去基团。各种高度官能化的烷基单元（例如官能团：烷基氯、醇、醛、胺、酰胺、硼酸酯、醚、酯、杂环、膦酸酯、张力环）被有效地结合在苄基位置。通过复杂生物活性化合物的后期修饰进一步证明了这种合成方法的实用性。初步的机理实验表明，该反应可能涉及自由基过程。
• Production method of polyhydroxyalkanoate form substituted fatty acid ester as raw material
  申请人：——

  公开号：US20020081646A1

  公开（公告）日：2002-06-27

  Polyhydroxyalkanoates comprising a monomer unit having the following chemical formula (2): 1 (where the reference characters R represents an arbitrarily selected substituent and x represents an integer of 0 to 8) is produced by culturing a microorganism in a culture medium containing a substituted fatty acid ester having the following chemical formula (1): 2 (where the reference characters R and R′ separately denote an optional substituent and x represents an integer of 0 to 8). The microorganism is capable of taking the substituted fatty acid ester into the cells and synthesizing the desired polyhydroxyalkanoate in the culture medium.

  通过在含有以下化学式（1）的取代脂肪酸酯的培养基中培养微生物，产生具有以下化学式（2）的单体单位的聚羟基烷酯（其中参考字符R代表任意选择的取代基，x代表0到8的整数）。该微生物能够将取代脂肪酸酯带入细胞并在培养基中合成所需的聚羟基烷酯。
• -Omega-aryl-alkylthienyl compounds, process for their preparation and pharmaceutical products containing these compounds
  申请人：A. Nattermann & Cie. GmbH

  公开号：EP0155524A1

  公开（公告）日：1985-09-25

  The invention relates to new omega-aryl-alkylthienyl compounds having the Formula I i.e. omega-aryl-alkyl thienyl alkanoic acids and, respectively, omega-aryl-alkyl correspondingly alkenoic acids, alkali metal salts of such acids and certain esters thereof. The invention further relates to process for producing the same, pharmaceutical products containing these compounds and the use of these compounds for the production of pharmaceutical preparations for the treatment of chronically inflammatory processes, for the treatment of various ulcers and in cancer therapy.

  本发明涉及具有式 I 的新ω-芳基-烷基噻吩化合物 即欧米伽-芳基-烷基噻吩基烷酸、欧米伽-芳基-烷基相应烯酸、这类酸的碱金属盐及其某些酯。本发明还涉及生产这些化合物的工艺、含有这些化合物的医药产品，以及使用这些化合物生产治疗慢性炎症过程、治疗各种溃疡和治疗癌症的药物制剂。
• Production method of polyhydroxyalkanoate from substituted fatty acid ester as raw material
  申请人：CANON KABUSHIKI KAISHA

  公开号：EP1201763A2

  公开（公告）日：2002-05-02

  Polyhydroxyalkanoates comprising a monomer unit having the following chemical formula (2): (where the reference characters R represents an arbitrarily selected substituent and x represents an integer of 0 to 8) is produced by culturing a microorganism in a culture medium containing a substituted fatty acid ester having the following chemical formula (1): (where the reference characters R and R' separately denote an optional substituent and x represents an integer of 0 to 8). The microorganism is capable of taking the substituted fatty acid ester into the cells and synthesizing the desired polyhydroxyalkanoate in the culture medium.

  聚羟基烷酸酯由具有以下化学式(2)的单体单元组成： (其中参考字符 R 代表任意选择的取代基，x 代表 0 至 8 的整数），通过在含有具有以下化学式（1）的取代脂肪酸酯的培养基中培养微生物而制得： (其中参考字符 R 和 R'分别表示任选取代基，x 表示 0 至 8 的整数）。微生物能够将取代脂肪酸酯带入细胞，并在培养基中合成所需的聚羟基烷酸酯。
• Fabritschnyi; et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2520,2522; engl. Ausg. 2556, 2558
  作者：Fabritschnyi、et al.

  DOI：——

  日期：——