ethyl 5-pentyl-1H-pyrazole-3-carboxylate | 89967-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-pentyl-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 5-pentylpyrazole-3-carboxylate
• CAS: 89967-33-9
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: PTQROBNHOISTRP-UHFFFAOYSA-N

物化性质

• 沸点：
  356.6±30.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-pentyl-1H-pyrazole-3-carboxylate 在 sodium hydroxide 作用下， 反应 5.0h， 以61.2%的产率得到5-Pentyl-2H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  降血脂药的研究。二。烷基吡唑衍生物的合成和药理性质。

  摘要：

  合成了一系列的5-烷基吡唑衍生物，并对其在大鼠中的有效降血脂活性进行了评估。发现许多在吡唑环的5位具有烷基的吡唑衍生物具有高降血脂活性。烷基链的同源性导致活性显着增加，但是在吡唑环上其他位点引入其他取代基未能增强活性。另外，用异恶唑环取代吡唑环导致活性显着降低。在测试的化合物中，5-n-十三烷基吡唑-3-羧酸（5k）表现出最有利的活性谱，并且与氯贝特一样有效。该化合物5k在急性试验（LD50 = 10.0g / kg）中显示出相当低的毒性，因此目前正在接受进一步的药理评估。

  DOI：

  10.1248/cpb.32.1568
• 作为产物：
  描述：

  2-庚酮 在 肼 作用下， 以 乙醇 为溶剂， 生成 ethyl 5-pentyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Agonist lead identification for the high affinity niacin receptor GPR109a

  摘要：

  A strategy for lead identification of new agonists of GPR109a, starting from known compounds shown to activate the receptor, is described. Early compound triage led to the formulation of a binding hypothesis and eventually to our focus on a series of pyrazole acid derivatives. Further elaboration of these compounds provided a series of 5,5-fused pyrazoles to be used as lead compounds for further optimization. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.028

文献信息

• Studies on Hypolipidemic Agents. II. Synthesis and Pharmacological Properties of Alkylpyrazole Derivatives
  作者：KUNIO SEKI、JUNICHI ISEGAWA、MINORU FUKUDA、MASAHIKO OHKI

  DOI：10.1248/cpb.32.1568

  日期：1984.4.25

  A series of 5-alkylpyrazole derivatives was synthesized and evaluated for potent hypolipidemic activity in rats. Many pyrazole derivatives with an alkyl group at the 5 position of the pyrazole ring were found to possess high hypolipidemic activity. Homologation of the alkyl chain led to marked increase in activity, but introduction of other substituents at other sites on the pyrazole ring failed to

  合成了一系列的5-烷基吡唑衍生物，并对其在大鼠中的有效降血脂活性进行了评估。发现许多在吡唑环的5位具有烷基的吡唑衍生物具有高降血脂活性。烷基链的同源性导致活性显着增加，但是在吡唑环上其他位点引入其他取代基未能增强活性。另外，用异恶唑环取代吡唑环导致活性显着降低。在测试的化合物中，5-n-十三烷基吡唑-3-羧酸（5k）表现出最有利的活性谱，并且与氯贝特一样有效。该化合物5k在急性试验（LD50 = 10.0g / kg）中显示出相当低的毒性，因此目前正在接受进一步的药理评估。
• Syntheses of heteroaromatic carboxylic acids closely related to fusaric acid.
  作者：HIROSHI YAMANAKA、MICHINAO MIZUGAKI、TAKAO SAKAMOTO、MATAICHI SAGI、YOSHIO NAKAGAWA、HIDEKI TAKAYAMA、MASATAKA ISHIBASHI、HIROSHI MIYAZAKI

  DOI：10.1248/cpb.31.4549

  日期：——

  In order to investigate the generality of a chain-elongation reaction observed in the metabolism of fusaric acid (5-butyl-2-pyridinecarboxylic acid) and its derivatives, various heteroaromatic (diazine, 1, 3-azole, and 1, 2-azole) carboxylic acids with a normal alkyl side-chain were synthesized.

  为了研究在fusari酸（5-丁基-2-吡啶酸）及其衍生物代谢中观察到的链延长反应的普遍性，合成了多种具有正常烷基侧链的杂芳香羧酸（嗪类、1,3-噁唑类和1,2-噁唑类）。
• Highly Regioselective Organocatalyzed Synthesis of Pyrazoles from Diazoacetates and Carbonyl Compounds
  作者：Lei Wang、Jiayao Huang、Xiaojie Gong、Jian Wang

  DOI：10.1002/chem.201300047

  日期：2013.6.3

  β‐ketoesters, β‐diketones, and aldehydes), as well as the operational simplicity of this process, a convenient, practical, and highly modular pyrazole synthesis has been developed. We believe that this work will arouse more research interest in the organocatalytic synthesis of other biologically active heterocycles. Such studies are currently underway in our laboratory.

  已经开发了一系列羰基化合物与重氮乙酸酯之间的一般有机催化逆电子需求[3 + 2]环加成反应。该反应被仲胺作为“绿色促进剂”催化，以生成具有高区域选择性的取代吡唑。值得注意的是，这种[3 + 2]环加成反应在室温下使用简单且廉价的催化剂即可有效地进行。考虑到起始原料（例如酮，β-酮酸酯，β-二酮和醛）的多样性和现成的可用性，以及该方法的操作简便性，已开发了一种方便，实用且高度模块化的吡唑合成方法。我们相信这项工作将在其他生物活性杂环的有机催化合成中引起更多的研究兴趣。
• 1,3-Dipolar cycloaddition of diazoacetate compounds to terminal alkynes promoted by Zn(OTf)2: an efficient way to the preparation of pyrazoles
  作者：Sheng He、Li Chen、Yan-Ning Niu、Lu-Yong Wu、Yong-Min Liang

  DOI：10.1016/j.tetlet.2009.03.030

  日期：2009.5

  A series of pyrazoles were prepared in good yields via 1,3-dipolar cycloaddition of diazoacetate compounds to terminal alkynes promoted by Zn(OTf)(2) under mild conditions. It was Supposed that the reaction was through the intermediate of Zn alkynilide. (C) 2009 Elsevier Ltd. All rights reserved.
• YAMANAKA, HIROSHI;MIZUGAKI, MICHINAO;SAKAMOTO, TAKAO;SAGI, MATAICHI;NAKAG+, CHEM. AND PHARM. BULL., 1983, 31, N 12, 4549-4553
  作者：YAMANAKA, HIROSHI、MIZUGAKI, MICHINAO、SAKAMOTO, TAKAO、SAGI, MATAICHI、NAKAG+

  DOI：——

  日期：——