环戊基噻吩-2-基酮 | 99186-05-7

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 环戊基噻吩-2-基酮
• 英文名称: cyclopentyl thien-2-yl ketone
• 英文别名: cyclopentyl-[2]thienyl ketone；Cyclopentyl-[2]thienyl-keton；2-Thienyl cyclopentyl ketone；cyclopentyl 2-thienyl ketone；Cyclopentyl(thiophen-2-yl)methanone
• CAS: 99186-05-7
• 化学式: C₁₀H₁₂OS
• mdl: MFCD09891340
• 分子量: 180.271
• InChiKey: ZLEDQHMUUGXXTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环戊基噻吩-2-基酮 在 溴 作用下， 以 四氯化碳 、 萘烷 为溶剂， 生成 2-(Methylamino)-2-thiophen-2-ylcyclohexan-1-one
  参考文献：
  名称：

  Discovery of novel ketamine‐inspired derivatives as a protective agent against renal ischemic/reperfusion injury in Wistar rats

  摘要：

  AbstractRenal ischemia‐reperfusion (I/R) injury is a limiting factor for the success of renal grafts and is deemed greatly responsible for the mortality. A novel series of ketamine‐inspired compounds was synthesized and subjected to NF‐ĸB transcriptional inhibitory activity in LPS‐stimulated RAW264.7 cells, where entire set of compounds showed mild‐to‐moderate significant NF‐ĸB transcriptional inhibitory activity (IC50 6.53–67.52 µM). Compound 6d showed highest inhibitory activity among the tested series (IC50 2.62 µM) and found more potent as compared to ketamine as standard. The effect of compound 6d was further quantified in I/R injury in Wistar rats, where it dose‐dependently improves kidney function of rats with significant amelioration of kidney injury as suggested by histopathologic examination of renal tissues. It further showed reduction in the generation of pro‐inflammatory cytokines and improves the antioxidant status of experimental rats. Compound 6d inhibited apoptosis and increases the expression of Bcl2 and decreases Bax, and cleaved caspase‐3 level. It further reduces TLR‐4 and NF‐κB expression in renal cells of rats, with increases in IκB‐α level in Western blot analysis as compared to I/R group. In summary, our current study showed the development of a novel class of ketamine‐inspired derivatives against renal ischemia/reperfusion injury.

  DOI：

  10.1111/cbdd.14011
• 作为产物：
  描述：

  在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到环戊基噻吩-2-基酮
  参考文献：
  名称：

  使用Sa试剂从柔性前体形成环戊烷

  摘要：

  这项研究提出了使用efficient（II）试剂合成五元环碳环的三种有效方法。简单的有机原料会参与分子内Reformatsky醇醛，烯醇烷基化和频哪醇环化反应。还建立了有希望的先导结果，证明了在手性配体控制的Reformatsky aldol反应中的对映选择性。

  DOI：

  10.1002/ejoc.201800102

文献信息

• Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the Construction of Quaternary Stereocenters
  作者：Hua Wu、Qian Wang、Jieping Zhu

  DOI：10.1021/jacs.9b04551

  日期：2019.7.24

  enantioselective pinacol rearrangement is ex-tremely challenging due to the likelihood involvement of the carbeni-um intermediate that renders the stereochemical communication between catalyst and substrate difficult to achieve. Herein, we report chiral N-triflyl phosphoramide-catalyzed enantioselective pinacol rearrangement of 1,2-tertiary diols and mechanistically related Meinwald rearrangement of tetrasubstituted

  对映选择性频哪醇重排的发展极具挑战性，因为碳鎓中间体可能参与其中，这使得催化剂和底物之间的立体化学通讯难以实现。在此，我们报告了手性 N-三氟甲基磷酰胺催化的 1,2-叔二醇的对映选择性频哪醇重排和机械相关的四取代环氧化物的 Meinwald 重排，用于合成对映体富集的 2-炔基-2-芳基环己酮和 2,2-环己酮二芳基分别。还记录了以催化对映选择性频哪醇重排为关键战略步骤的 (+)-膜的全合成。
• <i>N</i>-Arylsulfonylamidines; Part 2.¹A New Synthesis of Ketones from<i>N</i>′-Tosylamidines and Organolithium Compounds
  作者：Francesca Clerici、Maria Luisa Gelmi、Luisa Maria Rossi

  DOI：10.1055/s-1987-28159

  日期：——

  Tertiary N′-arylsulfonylamidines readily react with organolithium compounds under simple conditions to afford carbonyl compounds.

  第三级N′-芳基磺酰胺在简单条件下能与有机锂化合物迅速反应，生成羰基化合物。
• Tetracyclic compounds as dopamine agonists
  申请人：Abbott Laboratories

  公开号：US05597832A1

  公开（公告）日：1997-01-28

  A tetracyclic compound of the formula: ##STR1## wherein A and the atoms to which it is attached and the optional double bond represent a mono- or di-heterocyclic ring selected from: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X are specifically defined, which compounds are useful in the treatment of dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of substance abuse and other addictive behavior disorders, cognitive impairment and attention deficit disorder.

  该四环化合物的化学式为：##STR1## 其中A和连接它的原子以及可选的双键表示从以下选择的单环或双环杂环：##STR2## 其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和X具有特定定义。这些化合物在治疗多巴胺相关的神经、心理和心血管疾病以及物质滥用和其他成瘾行为障碍、认知障碍和注意力缺陷障碍方面非常有用。
• Synthesis of cyclopentyl 2-thienyl ketone, tiletamine and tiletamine
  申请人：Great Lakes Chemical Corporation

  公开号：US06147226A1

  公开（公告）日：2000-11-14

  A water-scavenging solvent, such a polyphosphoric acid, can be used for the synthesis of cyclopentyl 2-thienyl ketone by the direct acylation of cyclopentanecarboxylic acid without first reacting the cyclopentanecarboxylic acid with thionylchloride to form the acid chloride, while achieving new and unexpected yields. A tiletamine-free base can be made from the cyclopentyl 2-thienyl ketone with a halide in the presence of a solvent for the cyclopentyl 2-thienyl ketone to form a halogenated cyclopentane 2-thienyl ketone, aminating the halogenated cyclopentane 2-thienyl ketone by reaction with an amine, and subjecting the reaction product to thermal rearrangement, in a suitable solvent, and at a sufficient temperature to form tiletamine free base. Each step for the formation of tiletamine free base can be accomplished using the same solvent, e.g., dichlorobenzene so that intermediates need not be isolated between reactions.

  一种水蒸气捕集溶剂，例如聚磷酸，可以用于通过对环戊基羧酸进行直接酰化而不是先与硫酰氯反应形成酸氯化物的方法合成环戊基2-噻吩基酮，同时实现新的和意想不到的产量。在环戊基2-噻吩基酮存在的溶剂的存在下，可以通过与卤化物反应形成卤代环戊烷2-噻吩基酮，通过与胺反应氨化卤代环戊烷2-噻吩基酮，并在适当的溶剂中，以足够的温度使反应产物发生热重排，形成无瓦斯他明的碱。制备无瓦斯他明的每个步骤都可以使用相同的溶剂，例如二氯苯，因此在反应之间不需要分离中间体。
• Synthesis of cyclopentyl 2-thienyl ketone tiletamine and tiletamine acid
  申请人：Great Lakes Chemical Corporation

  公开号：US05969159A1

  公开（公告）日：1999-10-19

  Solid, non-tin-containing catalysts can be used for the synthesis of cyclopentyl 2-thienyl ketone by the reaction of cyclopentanecarboxylic acid chloride and thiophene, while achieving new and unexpected yields. Aluminum trichloride is both cheaper than stannic chloride and it is easier to deal with as a waste stream. The successful use of graphite as a catalyst for the reaction of cyclopentanecarboxylic acid chloride and thiophene provides a mild and ecologically friendly method for carrying out the Friedel-Crafts reaction. A tiletamine-free base can be made from the cyclopentyl 2-thienyl ketone with a halide in the presence of a solvent for the cyclopentyl 2-thienyl ketone to form a halogenated cyclopentane 2-thienyl ketone; aminating the halogenated cyclopentane 2-thienyl ketone by reaction with an amine; and subjecting the reaction product to thermal rearrangement, in a suitable solvent, and at a sufficient temperature to form tiletamine free base. Each step for the formation of tiletamine free base can be accomplished using the same solvent, e.g., dichlorobenzene so that intermediates need not be isolated between reactions.

  无锡催化剂可用于合成环戊基2-噻吩酮，反应为环戊基羧酸氯化物和噻吩的反应，同时实现了新的和意外的产量。三氯化铝比氯化锡更便宜且更易于处理废液。成功地使用石墨作为催化剂，对环戊基羧酸氯化物和噻吩的反应提供了一种温和且环保的费托合成反应方法。可以在环戊基2-噻吩酮存在溶剂的情况下，通过卤化物制备出无托咪定自由基，形成卤代环戊烷2-噻吩酮；通过与胺反应使卤代环戊烷2-噻吩酮进行胺化作用；并在适当的溶剂中，以足够的温度对反应产物进行热重排，形成无托咪定的自由基。制备无托咪定自由基的每个步骤都可以使用相同的溶剂，例如二氯苯，因此反应之间不需要分离中间产物。