2-(4,5-二氢-3H-吡咯-2-基)-吡啶 | 66269-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(4,5-二氢-3H-吡咯-2-基)-吡啶
• 英文名称: 4-(3,4-dihydro-2H-pyrrol-5-yl)pyridine
• 英文别名: 4-(4,5-dihydro-3H-pyrrol-2-yl)-pyridine；2-Pyridyl-(4)-Δ¹-pyrrolin, 4,2'-Myosmin；4-Myosmin
• CAS: 66269-78-1
• 化学式: C₉H₁₀N₂
• mdl: MFCD09749689
• 分子量: 146.192
• InChiKey: PGUPWKBFABLBCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(4,5-二氢-3H-吡咯-2-基)-吡啶 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 4-nornicotine
  参考文献：
  名称：

  Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers

  摘要：

  Design and synthesis of pyrazolodihydropyrimidines as K(V)1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.085
• 作为产物：
  描述：

  3-Isonicotinoyl-pyrrolidon-(2) 在 盐酸 作用下， 生成 2-(4,5-二氢-3H-吡咯-2-基)-吡啶
  参考文献：
  名称：

  C 2 F 5 Li的制备及其与环亚胺和乳酸亚胺反应的新方法：α-五氟乙基脯氨酸的合成

  摘要：

  在环亚胺上添加五氟乙基锂会产生五氟乙基取代的吡咯烷，哌啶和氮杂环庚烷，而环内酰胺的反应会生成2-五氟乙基亚胺。已经发现2-呋喃基-2-五氟乙基吡咯烷的氧化裂解是制备外消旋α-五氟乙基脯氨酸的有效方法。

  DOI：

  10.1016/j.jfluchem.2008.01.013

文献信息

• Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups
  作者：Nikolay E. Shevchenko、Gerd-Volker Röschenthaler、Alexander S. Mitiaev、Enno Lork、Valentine G. Nenajdenko

  DOI：10.1016/j.jfluchem.2008.05.005

  日期：2008.7

  β-Hydroxymethyl substituted cyclic imines or imidates are formed as a result of the reaction. The reduction of the prepared imines leads stereoselectively to the cyclic 1,3-aminoalcohols. Application of methyl trifluoropyruvate in this transformation opens an opportunity for the synthesis of γ-aminoacids derivatives which contain pyrrolidine moiety.

  在温和条件下，没有任何催化剂的情况下，环亚胺和环内酰胺与通过吸电子三氟甲基或三氯甲基基团活化的羰基化合物的醛醇缩合反应得以进行。反应的结果是形成β-羟甲基取代的环状亚胺或酰亚胺。制备的亚胺的还原立体选择性地产生环状的1，3-氨基醇。在该转化中三氟丙酮酸甲酯的应用为合成包含吡咯烷部分的γ-氨基酸衍生物提供了机会。
• Efficient Synthesis of Substituted Cyclic α-Aminophosphonates
  作者：Irina Odinets、Oleg. Artyushin、Nikolay Shevchenko、Pavel Petrovskii、Valentin Nenajdenko、Gerd-Volker Röschenthaler

  DOI：10.1055/s-0028-1083349

  日期：2009.2

  The addition of diethyl phosphite to cyclic imines bearing alkyl, aryl, or heteroaryl substituents at the α-position in diethyl ether at room temperature presents an efficient route to substituted cyclic α-aminophosphonates. The application of boron trifluoride-diethyl ether complex as a catalyst significantly accelerates the reaction. diethyl phosphonate - cyclic imines - addition reactions - α-aminophosphonates

  在室温下，将亚磷酸二乙酯加到在亚乙基醚的α位上带有烷基，芳基或杂芳基取代基的环状亚胺上，提供了一种取代环状α-氨基膦酸酯的有效途径。使用三氟化硼-乙醚复合物作为催化剂可显着加速反应。 膦酸二乙酯-环状亚胺-加成反应-α-氨基膦酸酯
• Aqueous Aldol Catalysis by a Nicotine Metabolite
  作者：Tobin J. Dickerson、Kim D. Janda

  DOI：10.1021/ja017774f

  日期：2002.4.1

  Nornicotine, an endogenous tobacco alkaloid and minor nicotine metabolite, can catalyze aldol reactions at physiological pH. Catalysis appears to be due to a covalent enamine mechanism, an unprecedented reaction with small organic molecule catalysts in aqueous buffer. Kinetic parameters for nornicotine as well as other related alkaloids were measured and demonstrate that both the pyrrolidine and pyridine rings are critical for optimal catalysis. Substrate compatibility of this catalyst and its implications in vivo are discussed.
• New method of preparation of C2F5Li and its reactions with cyclic imines and lactims: Synthesis of α-pentafluoroethyl proline
  作者：Nikolay E. Shevchenko、Valentine G. Nenajdenko、Gerd-Volker Röschenthaler

  DOI：10.1016/j.jfluchem.2008.01.013

  日期：2008.5

  Addition of pentafluoroethyllithium to cyclic imines leads to pentafluoroethyl substituted pyrrolidines, piperidines and azepanes while reaction of cyclic lactims gives rise to 2-pentafluoroethyl imines. Oxidative cleavage of 2-furyl-2-pentafluoroethyl pyrrolidine has been found to be an effective method for the preparation of a racemic α-pentafluoroethyl proline.

  在环亚胺上添加五氟乙基锂会产生五氟乙基取代的吡咯烷，哌啶和氮杂环庚烷，而环内酰胺的反应会生成2-五氟乙基亚胺。已经发现2-呋喃基-2-五氟乙基吡咯烷的氧化裂解是制备外消旋α-五氟乙基脯氨酸的有效方法。
• Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers
  作者：John Lloyd、Heather J. Finlay、Wayne Vacarro、Tram Hyunh、Alexander Kover、Rao Bhandaru、Lin Yan、Karnail Atwal、Mary Lee Conder、Tonya Jenkins-West、Hong Shi、Christine Huang、Danshi Li、Huabin Sun、Paul Levesque

  DOI：10.1016/j.bmcl.2009.12.085

  日期：2010.2

  Design and synthesis of pyrazolodihydropyrimidines as K(V)1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development. (C) 2010 Elsevier Ltd. All rights reserved.