methyl ester of trans-β-(morpholino)acrylic acid | 101471-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: methyl ester of trans-β-(morpholino)acrylic acid
• 英文别名: trans-N-β-Morpholinoacrylic acid methyl ester；trans-1-methoxycarbonyl-2-morpholylethylene；(E)-methyl 3-(morpholin-4-yl)prop-2-enoate；methyl (E)-3-(4-morpholinyl)-2-propenoate；methyl-(2E)-3-(morpholin-4-yl)acrylate；methyl β-morphinoacrylate；Methyl (E)-3-Morpholinoacrylate；methyl (E)-3-morpholin-4-ylprop-2-enoate
• CAS: 101471-73-2
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: XFGDIQBAFODGRV-NSCUHMNNSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  263.4±40.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl ester of trans-β-(morpholino)acrylic acid 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到methyl 2,6-dimethyl-4H-pyran-4-one-3-carboxylate
  参考文献：
  名称：

  Kang, G. J.; Chan, T. H., Canadian Journal of Chemistry, 1985, vol. 63, p. 3102 - 3110

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-<2-(morpholin-4-yl)vinyl>-1H-indole 生成 methyl ester of trans-β-(morpholino)acrylic acid
  参考文献：
  名称：

  MEDION-SIMON, MERCEDES;PINDUR, ULF, HELV. CHIM. ACTA, 74,(1991) N, C. 430-437

  摘要：

  DOI：

文献信息

• Highly Site-Selective Metal-Free C–H Acyloxylation of Stable Enamines
  作者：Fei Wang、Wangbing Sun、Yixin Wang、Yaojia Jiang、Teck-Peng Loh

  DOI：10.1021/acs.orglett.8b00222

  日期：2018.2.16

  A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as

  描述了在无金属条件下用Phi（OAc）2对稳定的烯胺进行高度位点选择性的酰氧基化，从而以良好或优异的收率得到（E）-乙酸乙烯酯衍生物。取决于溶剂系统的明智选择，可以高选择性获得α-位或β-位选择性产物。对于α-位选择产物，获得了重排的酰胺化合物作为主要产物。该反应在温和的反应条件下（室温，无金属和烧瓶）进行，并且具有广泛的底物范围。
• Palladium-Catalyzed C-S Bond Formation of Stable Enamines with Arene/Alkanethiols: Highly Regioselective Synthesis of β-Amino Sulfides
  作者：Yaojia Jiang、Gaohui Liang、Cong Zhang、Teck-Peng Loh

  DOI：10.1002/ejoc.201600588

  日期：2016.7

  A direct and regiocontrolled thiolation method to access β-amino sulfides through the palladium-catalyzed C(sp2)–H functionalization of stable enamines was described. The reaction was realized under mild conditions by adding an external phosphine ligand to prevent poisoning of the palladium catalyst by the sulfuric reagents. A possible mechanism was proposed according to the obtained results. The DFT

  描述了一种通过钯催化的稳定烯胺的 C(sp2)-H 官能化获得 β-氨基硫化物的直接和区域控制的硫醇化方法。该反应在温和条件下通过添加外部膦配体来实现，以防止钯催化剂被硫酸试剂中毒。根据所得结果提出了一种可能的机制。DFT 计算结果与实验数据一致，给出了 β-氨基硫化物的 E 异构体。该反应也以克规模进行，并显示出在有机合成中的潜在应用。
• Lewis Acid-Catalyzed [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen-Functionalized Cyclopentane Derivatives
  作者：Kamal Verma、Prabal Banerjee

  DOI：10.1002/adsc.201600221

  日期：2016.6.30

  efficient method for the synthesis of nitrogen‐functionalized cyclopentane derivatives via [3+2] cycloaddition of enamines with donor‐acceptor cyclopropanes in the presence of catalytic amounts of various Lewis acids at room temperature has been developed; furthermore, the corresponding β‐amino acid was synthesized by monodecarboxylation and hydrogenolysis. An enantioenriched synthesis of nitrogen‐functionalized

  在室温下催化量的各种路易斯酸存在下，开发了一种简单有效的方法，可通过烯胺与供体-受体环丙烷的[3 + 2]环加成反应，合成氮官能化的环戊烷衍生物；此外，通过单脱羧和氢解合成了相应的β-氨基酸。通过外消旋给体-受体环丙烷的动态动力学不对称转化，对氮官能化的环戊烷衍生物进行了对映体富集合成，采用铜络合物[Cu（OTf）2 - L1 ]作为催化剂，对映体比例高达8：1。
• 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。