1-((E)-hept-1-enyl)pyrrolidin-2-one | 117593-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-((E)-hept-1-enyl)pyrrolidin-2-one
• 英文别名: N-((E)-hept-1-enyl)pyrrolidin-2-one；N-((E)-1-heptenyl)-2-pyrrolidinone；N-(1-E-heptenyl)-2-pyrrolidinone；1-heptenyl-2-pyrrolidone；N-(Hept-1-enyl)-pyrrolidin-2-one；1-[(E)-hept-1-enyl]pyrrolidin-2-one
• CAS: 117593-77-8；112518-06-6
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: UMEYVEUACVDOOE-RMKNXTFCSA-N

物化性质

• 沸点：
  300.3±9.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triethyloxonium fluoroborate 、 1-((E)-hept-1-enyl)pyrrolidin-2-one 以 二氯甲烷 为溶剂， 以100%的产率得到2-ethoxy-N-((E)-1-heptenyl)-pyrrolidiniminium tetrafluoroborate
  参考文献：
  名称：

  N-烯基-亚胺盐的狄尔斯-阿尔德反应：获得吲哚里西啶衍生物的新途径

  摘要：

  摘要 N-链烯基-2-乙氧基亚胺鎓盐与简单烯烃的狄尔斯-阿尔德反应在硝基甲烷中加热后得到狄尔斯-阿尔德环加合物。用氢化物减少难处理的环加合物导致吲哚里西啶生物碱的产率低到中等。

  DOI：

  10.1080/00397919308009776
• 作为产物：
  描述：

  1-((Z)-hept-1-enyl)pyrrolidin-2-one 在 十羰基二铼 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 1-((E)-hept-1-enyl)pyrrolidin-2-one
  参考文献：
  名称：

  Rhenium-Catalyzed Hydroamidation of Unactivated Terminal Alkynes:  Synthesis of (E)-Enamides

  摘要：

  Reactions of cyclic amides with unactivated terminal alkynes in the presence of a catalytic amount of a rhenium complex provided (E)enamides in high regio- and stereoselectivity (E:Z = > 99:< 1).

  DOI：

  10.1021/ol702564e

文献信息

• Synthesis of sterically hindered enamides via a Ti-mediated condensation of amides with aldehydes and ketones
  作者：Julien Genovino、Bharat Lagu、Yaping Wang、B. Barry Touré

  DOI：10.1039/c2cc32538a

  日期：——

  The first TiCl(4)-mediated condensation of secondary amides with aldehydes and ketones has been achieved. The reaction proceeds at room temperature and is complete within 5 h in most cases. The optimized procedure used 5 equiv of an amine base hinting that the in situ activation of both the amide and the Lewis acid is required. The reaction affords polysubstituted (E)-enamides.

  已经实现了第一个TiCl（4）介导的仲酰胺与醛和酮的缩合。反应在室温下进行，在大多数情况下，反应会在5小时内完成。优化的程序使用了5当量的胺碱，这暗示着需要酰胺和路易斯酸的原位活化。反应得到多取代的（E）-酰胺。
• Z-Selective hydroamidation of terminal alkynes with secondary amides and imides catalyzed by a Ru/Yb-system
  作者：Annette E. Buba、Matthias Arndt、Lukas J. Gooßen

  DOI：10.1016/j.jorganchem.2010.08.034

  日期：2011.1

  to catalyze the addition of nitrogen nucleophiles to terminal alkynes under mild conditions to stereoselectively form the Z-enamide or Z-enimide products. Various secondary amides and imides could be added across the triple bond of a range of aliphatic and aromatic alkynes. The new bimetallic catalyst system sets new standards with regard to scope and selectivity for the synthesis of Z-configured anti-Markovnikov

  形成的催化剂体系的原位从双（2-甲基烯丙基）环辛-1,5-二烯钌（II）[（COD）的Ru（满足）2 ]，1,4-双（二环己基膦）丁烷（dcypb）和镱发现（III）三氟甲磺酸盐水合物（Yb（OTf）3）在温和条件下催化氮亲核试剂向末端炔烃的加成，以立体选择性地形成Z-烯酰胺或Z-烯酰亚胺产物。可以跨一系列脂族和芳族炔的三键添加各种仲酰胺和酰亚胺。新的双金属催化剂体系就合成Z-构型的反-Markovnikov酰胺类化合物的范围和选择性设定了新的标准。
• Lobatamide C:  Total Synthesis, Stereochemical Assignment, Preparation of Simplified Analogues, and V-ATPase Inhibition Studies
  作者：Ruichao Shen、Cheng Ting Lin、Emma Jean Bowman、Barry J. Bowman、John A. Porco

  DOI：10.1021/ja0352350

  日期：2003.7.1

  The total synthesis and stereochemical assignment of the potent antitumor macrolide lobatamide C, as well as synthesis of simplified lobatamide analogues, is reported. Cu(I)-mediated enamide formation methodology has been developed to prepare the highly unsaturated enamide side chain of the natural product and analogues. A key fragment coupling employs base-mediated esterification of a beta-hydroxy

  报告了有效的抗肿瘤大环内酯洛巴胺 C 的全合成和立体化学分配，以及简化的洛巴胺类似物的合成。已开发出 Cu(I) 介导的烯酰胺形成方法来制备天然产物和类似物的高度不饱和烯酰胺侧链。关键片段偶联采用碱介导的 β-羟基酸和水杨酸氰甲基酯的酯化。已使用相关合成路线制备了三种额外的洛巴胺 C 立体异构体。lobatamide C 的 C8、C11 和 C15 的立体化学是通过立体异构体的比较和结晶衍生物的 X 射线分析来确定的。合成的洛巴胺 C、立体异构体和简化的类似物已被评估用于抑制牛嗜铬颗粒膜 V-ATP 酶。水杨酸苯酚，
• PROCESS FOR PRODUCING AZACYCLOALKANE DERIVATIVE
  申请人：HISAMITSU PHARMACEUTICAL CO. INC.

  公开号：EP0555483A1

  公开（公告）日：1993-08-18

  A process for producing an azacycloalkane derivative represented by general formula (II), wherein m represents an integer of 1 to 3, n₂ represents an integer of 2 to 10, and R represents C₃ to C₁₂ alkyl, which comprises reacting 1-(n-alkenyl)azacycloalkan-2-one represented by general formula (I) wherein, m is as defined above and n₁ represents an integer of 0 to 8, with an alkyl mercaptan in the presence of a radical initiator in an organic solvent, treating the reaction product with a reducing agent in a watery organic solvent, followed by purification through distillation.

  一种生产通式(II)代表的氮杂环烷衍生物的工艺，其中m代表1至3的整数，n₂代表2至10的整数，R代表C₃至C₁₂烷基，该工艺包括使通式(I)代表的1-(n-烯基)氮杂环烷-2-酮在有机溶剂中与烷基硫醇反应，其中、m 如上定义，n₁ 代表 0 至 8 的整数，在有机溶剂中，在自由基引发剂存在下，与烷基硫醇反应，在含水有机溶剂中，用还原剂处理反应产物，然后通过蒸馏提纯。
• Synthesis and reactivity of hexahydropyrroloquinolines
  作者：Mark Hadden、Mark Nieuwenhuyzen、Deirdre Potts、Paul J Stevenson、Norris Thompson

  DOI：10.1016/s0040-4020(01)00466-5

  日期：2001.6

  Formal [4+2] cycloaddition of cyclic enamides with imines derived from aromatic amines gave the 4-arylhexahydropyrroloquinoline skeleton in one step as mixtures of diastereoisomers. Aromatic imines derived from formaldehyde and methylglyoxalate also participated in this chemistry, with the latter favouring formation of the endo-cycloadduct. The cycloadducts derived from methylglyoxalate were unstable and fragmented to give highly substituted quinolines under both neutral and basic conditions. Imines derived from 3-cyanoacrolein also underwent cycloaddition and gave an advanced potential precursor to martinellic acid, albeit with poor diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.