(E)-methyl 3-(piperidin-1-yl)acrylate | 5762-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-methyl 3-(piperidin-1-yl)acrylate
• 英文别名: methyl (E)-3-(piperidin-1-yl)acrylate；methyl β-piperdinoacrylate；methyl 3-piperidinoacrylate；methyl 3-piperidin-1-ylacrylate；β-Piperidino-acrylsaeure-methylester；methyl (E)-3-piperidin-1-ylprop-2-enoate
• CAS: 5762-45-8；7542-91-8；90608-65-4
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: PWNDAFWDGNCTOK-VMPITWQZSA-N

物化性质

• 沸点：
  248.2±19.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (E)-methyl 3-(piperidin-1-yl)acrylate 以 四氢呋喃 为溶剂， 生成 methyl 5-oxo-2-piperidin-1-yl-4-[3-(trifluoromethyl)phenyl]-4H-indeno[1,2-b]pyran-3-carboxylate
  参考文献：
  名称：

  A convenient route to polyfunctionalised indeno[ 1,2 - b ]pyran derivatives

  摘要：

  2-Arylidene-1,3-indanediones undergo facile formal hetero-Diels-Alder cycloadditions with ynamines bearing electron-withdrawing groups yielding polyfunctionalised indeno[1,2-b]pyrans.

  DOI：

  10.1016/0040-4039(91)80626-h
• 作为产物：
  描述：

  (E)-methyl 3-(piperidin-1-yl)acrylate 在 环己胺 作用下， 以 乙腈 为溶剂， 生成 (E)-methyl 3-(piperidin-1-yl)acrylate
  参考文献：
  名称：

  Breus, V. A.; Neklyudov, S. A.; Solomonov, B. N., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 9, p. 1843 - 1844

  摘要：

  DOI：

文献信息

• Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c1gc15701a

  日期：——

  A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis. The regio- and stereo-chemistry of the products were established by IR, NMR and single crystal X-ray analysis.

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。
• Efficient synthesis of β-enaminoesters via highly stereoselective Reformatsky reaction with disubstituted formamides as novel electrophiles
  作者：Yi-Yin Ke、Yu-Jin Li、Jian-Hong Jia、Wei-Jian Sheng、Liang Han、Jian-Rong Gao

  DOI：10.1016/j.tetlet.2009.01.003

  日期：2009.4

  An efficient synthesis of various β-enaminoesters has been achieved via Reformatsky reaction with disubstituted formamides as novel electrophiles. The exclusive β-enaminoester E-isomers were obtained in 60–72% yield.

  通过与二取代甲酰胺作为新型亲电试剂的Reformatsky反应，已实现了各种β-烯氨基酯的有效合成。以60–72％的产率获得了独家的β-烯氨基酯E-异构体。
• Synthesis of 2-aminofurans and 2-unsubstituted furans via carbenoid-mediated [3 + 2] cycloaddition
  作者：Yaojia Jiang、Vanessa Zhong Yue Khong、Emmanuvel Lourdusamy、Cheol-Min Park

  DOI：10.1039/c2cc18139h

  日期：——

  An efficient dual synthetic manifold for 2-aminofurans and 2-unsubstituted furans has been developed. The carbenoid-mediated [3 + 2] cycloaddition of copper carbenoids with enamines provides 2-amino-2,3-dihydrofurans which serve as common intermediates for both 2-aminofurans and 2-unsubstituted furans.

  一种高效的双重合成途径已被开发，用于2-氨基呋喃和未取代的呋喃。通过铜卡宾与烯胺的[3 + 2]环加成反应，生成了2-氨基-2,3-二氢呋喃，这些作为2-氨基呋喃和未取代呋喃的共同中间体。
• α-Cyclization of tertiary amines. Part 1
  作者：Shuiping Jiang、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/0040-4039(94)88019-0

  日期：1994.2

  A general, diastereoselective synthesis of functionalised pyrrolidine, indolizidine, pyrrolizidine and its seven-, eight-membered homologues is reported, starting from readily available enamine esters and acetylenedicarboxylate (DMAD).

  据报道，从容易获得的烯胺酯和乙炔二羧酸酯（DMAD）开始，对官能化的吡咯烷，吲哚并立唑，吡咯烷并其七，八元同系物进行了一般的非对映选择性合成。
• α-Cyclization of tertiary amines. Part 3. Captodative or push-pull enamines form pyrrolines, pyrrolizidines and their ring homologues with dimethyl acetylenedicarboxylate in a highly diastereoselective reaction
  作者：Benoît De Boeck、Shuiping Jiang、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/s0040-4020(01)85235-2

  日期：1994.1

  The title one-pot reaction occurs through a sequence of [2+2] cycloaddition, ring opening to dienamines and formation of a 1,5-dipole by [1,6] hydrogen-shift. This intermediate may cyclize or, in sterically suitable cases and at lower temperatures, lead to isolable N-vinyl enamines by proton transfer.

  通过[2 + 2]环加成，二烯胺开环和通过[1,6]氢转移形成1,5-偶极的过程发生标题一锅反应。该中间体可环化，或在空间上合适的情况下且在较低温度下通过质子转移产生可分离的N-乙烯基烯胺。