ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate | 116614-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate
• 英文别名: ethyl (E)-(1-benzyl-2-pyrrolidinylidene)acetate；ethyl (2E)-2-(1-benzylpyrrolidin-2-ylidene)acetate
• CAS: 116614-85-8
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: YXWXNWRCSDUVPD-SDNWHVSQSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  375.0±41.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以88%的产率得到(1-benzyl-pyrrolidin-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

  摘要：

  The conditions of the Eschenmoser coupling reaction were studied. The formation of the alpha-thioiminium ion was achieved faster in the presence of an additive (Nal) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.081
• 作为产物：
  描述：

  1-benzyl-2-pyrrolidinethione 在 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.55h， 生成 ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate
  参考文献：
  名称：

  硫挤出反应：一种新的β-烯氨基内酯合成

  摘要：

  摘要 α-溴内酯 4 与硫代内酰胺 3 缩合通过硫化物收缩序列形成 β-烯氨基内酯 2a-g。

  DOI：

  10.1080/00397919408010570

文献信息

• C(sp³)–H dehydrogenation and C(sp²)–H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles
  作者：Yan He、Fang Wang、Xinying Zhang、Xuesen Fan

  DOI：10.1039/c6cc10227a

  日期：——

  A novel and efficient synthesis of tetrahydropyridine-, dihydropyrrole-, and tetrahydroazepine-3-carboxylates via cascade reactions of cyclic amines with CO and alcohols is presented. To our knowledge, this should be the first example in which functionalized N-heterocycles were prepared through Pd-catalyzed C(sp3)-H dehydrogenation and C(sp2)-H carbonylation of cyclic amines.

  通过环胺与CO和醇的级联反应，提出了一种新颖而有效的四氢吡啶-，二氢吡咯-和四氢氮杂-3-羧酸酯的合成方法。据我们所知，这应该是第一个通过钯催化环胺的C（sp 3）-H脱氢和C（sp 2）-H羰基化制备N杂环的例子。
• Tertiary amide-based Knoevenagel-type reactions: a direct, general, and chemoselective approach to enaminones
  作者：Pei-Qiang Huang、Wei Ou、Kai-Jiong Xiao、Ai-E Wang

  DOI：10.1039/c4cc03826f

  日期：——

  We report one-pot and chemoselective Knoevenagel-type reactions using highly stable amides and lactams as the electrophilic substrates. The method is based on the in situ activation of amide carbonyl with triflic anhydride and a subsequent reaction with carbanions generated in situ from carbonyl compounds. The amide-based method is an alternative to the versatile thioamide-based Eschenmoser sulfide contraction.

  我们报告了以高度稳定的酰胺和内酰胺为亲电底物的一锅化学选择性克诺文纳格尔型反应。该方法基于酰胺羰基与三酸酐的原位活化，以及随后与羰基化合物原位生成的碳离子反应。这种基于酰胺的方法是基于硫代酰胺的埃申莫瑟硫化收缩法的替代方法。
• Syntheses of alkyl (E)-(1-aryl-2-pyrrolidinylidene)acetates
  作者：Joseph P. Michael、Gladys D. Hosken、Arthur S. Howard

  DOI：10.1016/s0040-4020(88)90042-7

  日期：1988.1
• MICHAEL, JOSEPH P.;HOSKEN, GLADYS D.;HOWARD, ARTHUR S., TETRAHEDRON, 44,(1988) N 10, 3025-3036
  作者：MICHAEL, JOSEPH P.、HOSKEN, GLADYS D.、HOWARD, ARTHUR S.

  DOI：——

  日期：——