methyl (Z)-2-acetamido-3-(3-pyridyl)acrylate | 115167-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (Z)-2-acetamido-3-(3-pyridyl)acrylate
• 英文别名: methyl (Z)-2-acetamido-3-(3-pyridyl)propenoate；methyl (Z)-2-acetamido-3-pyridin-3-ylprop-2-enoate
• CAS: 115167-43-6
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: DFTJYFDVYCOXEP-POHAHGRESA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  449.6±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-acetamido-3-(3-pyridyl)acrylate 在 tetrafluoroboric acid 、 氯化亚砜 、 (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、500.01 kPa 条件下， 反应 36.0h， 生成 (S)-methyl 2-amino-3-(pyridin-3-yl)propanoate
  参考文献：
  名称：

  Synthesis and Antimycobacterial Activity of 2,1′-Dihydropyridomycins

  摘要：

  Dihydropyridomycins 2 and 3, which lack the characteristic enol ester moiety of the potent antimycobacterial natural product pyridomycin (1), have been prepared from L-Thr, R- and S-hydroxy isovaleric acid, and 3-pyridinecarboxaldehyde. The 2R isomer 2 shows only 4-fold lower anti-Mtb activity than 1, indicating that the enol ester moiety in the natural product is not critical for its biological activity. This finding establishes 2 as a potent and more practical lead for anti-TB drug discovery.

  DOI：

  10.1021/ml300385q
• 作为产物：
  描述：

  3-吡啶甲醛 在 sodium acetate 、 乙酸酐 作用下， 反应 90.0h， 生成 methyl (Z)-2-acetamido-3-(3-pyridyl)acrylate
  参考文献：
  名称：

  Synthesis and Antimycobacterial Activity of 2,1′-Dihydropyridomycins

  摘要：

  Dihydropyridomycins 2 and 3, which lack the characteristic enol ester moiety of the potent antimycobacterial natural product pyridomycin (1), have been prepared from L-Thr, R- and S-hydroxy isovaleric acid, and 3-pyridinecarboxaldehyde. The 2R isomer 2 shows only 4-fold lower anti-Mtb activity than 1, indicating that the enol ester moiety in the natural product is not critical for its biological activity. This finding establishes 2 as a potent and more practical lead for anti-TB drug discovery.

  DOI：

  10.1021/ml300385q

文献信息

• PYRIDOMYCIN BASED COMPOUNDS EXHIBITING AN ANTITUBERCULAR ACTIVITY
  申请人：ETH Zurich

  公开号：US20150246907A1

  公开（公告）日：2015-09-03

  Formula (1), X 1 represents O or NR 6 , X 2 represents O or NR 6 , X 3 represents O or NR 1 , R 1 represents H or C 1 to C 3 alkyl, R 2 represents H, or linear or branched C 1 -C 8 alkyl optionally including one or more heteroatoms, cyclopropyl, cyclobutyl, cyclohexyl or oxetanyl or amino acid side chain or protected amino acid side chain, or R 1 and R 2 may form together a saturated, partly saturated or unsaturated 5 or 6 membered ring system, optionally substituted, R 3 represents H, cyclopentyl, cyclohexyl, aryl or hydroxyaryl, aryl or hydroxyaryl being optionally substituted by fluorine, or linear or branched C 1 to C 8 alkyl optionally including a hetero atom, R 4 represents phenyl or 5- or 6-membered heterocycles including one or more nitrogen or oxygen atoms optionally substituted with 1 to 4, respectively 5 fluorine atoms, and R 6 represents H, or linear or branched alkyl chain having 1 to 3 carbon atoms.

  公式（1），X1代表O或NR6，X2代表O或NR6，X3代表O或NR1，R1代表H或C1到C3烷基，R2代表H，或线性或支链的C1-C8烷基，可选地包括一个或多个杂原子，环丙基，环丁基，环己基或氧环丙基或氨基酸侧链或保护的氨基酸侧链，或R1和R2可以形成一个饱和的，部分饱和的或不饱和的5或6成员环系统，可选地取代，R3代表H，环戊基，环己基，芳基或羟基芳基，芳基或羟基芳基可选地被氟取代，或线性或支链的C1到C8烷基，可选地包括一个杂原子，R4代表苯或包括一个或多个氮或氧原子的5-或6成员杂环，可选地用1到4，分别用5氟原子取代，R6代表H，或具有1到3个碳原子的线性或支链烷基链。
• Practical Enantioselective Hydrogenation of α-Aryl- and α-Carboxyamidoethylenes by Rhodium(I)-{1,2-Bis[(<i>o</i>-<i>tert</i>-butoxyphenyl)(phenyl)phosphino]ethane}
  作者：Barbara Mohar、Michel Stephan

  DOI：10.1002/adsc.201200780

  日期：——

  The rhodium(I)-1,2-bis[(o-tert-butoxyphenyl)(phenyl)phosphino]ethane} [Rh(I)-(t-Bu-SMS-Phos)] catalyst system displayed prime efficiency in the hydrogenation of large series of α-amidostyrenes and α-amidoacrylates. Up to >99.9% enantiomeric excesses coupled with very high reaction rates were attained operating routinely under 1–10 bar of hydrogen at 22 °C in methanol. Examples include industrial substrates

  铑（I） - 1,2-二[（ø -叔-butoxyphenyl）（苯基）膦基〕乙烷}的[Rh（I） - （叔卜-SMS-PHOS）]的催化剂体系显示优越的效率大系列α-酰胺基苯乙烯和α-酰胺基丙烯酸酯的氢化。在22°C的甲醇中，在1-10 bar的氢气下，常规操作可获得高达> 99.9％的对映异构体过量以及极高的反应速率。实例包括工业基材。
• CHIRAL PHOSPHOROUS COMPOUNDS
  申请人：Gilheany Declan

  公开号：US20100168456A1

  公开（公告）日：2010-07-01

  The present invention provides P-chiral compounds of general formulae (II) and (III): in formula (II) at least one of R 21 , R 25 , R 26 and R 30 is independently selected from CM alkyl, CF 3 , C 1-4 alkoxy, phenyl and benzyloxy and the remaining substituents selected from R 21 , R 25 , R 26 and R 30 are hydrogen; at least one of R 22, R 24, R 27 and R 29 are independently selected from C 1-14 alkyl, CF 3, C 1-14 alkoxy, phenyl and benzyloxy and the remaining substituents selected, from R 22 , R 24, R 27 and R 29 are hydrogen; and R 23 and R28 are independently selected from hydrogen, CM alkyl, CF 3 , C 1-14 alkoxy, phenyl and benzyloxy; in formula (III) at least one of R 21 , R 25 , R 26 and R 30 is independently selected from phenyl and benzyloxy and the remaining substituents selected from R 21 , R 25 , R— 26 and R 30 are hydrogen; and R 22 , R— 23 R 24, R 27 , R 28 and R 29 are independently selected from hydrogen, C 1-14 alkyl, CF 3 , C 1-14 alkoxy, phenyl and benzyloxy.

  本发明提供了一般式（II）和（III）的P-手性化合物：在式（II）中，R21、R25、R26和R30中至少有一个是独立选择的CM烷基，CF3，C1-4烷氧基，苯基和苄氧基，其余取代基选择自R21、R25、R26和R30为氢；R22、R24、R27和R29中至少有一个是独立选择的C1-14烷基，CF3，C1-14烷氧基，苯基和苄氧基，其余取代基选择自R22、R24、R27和R29为氢；R23和R28独立选择自氢，CM烷基，CF3，C1-14烷氧基，苯基和苄氧基；在式（III）中，R21、R25、R26和R30中至少有一个是独立选择的苯基和苄氧基，其余取代基选择自R21、R25、R-26和R30为氢；R22、R-23、R24、R27、R28和R29独立选择自氢，C1-14烷基，CF3，C1-14烷氧基，苯基和苄氧基。
• Impact on Hydrogenation Catalytic Cycle of the R Groups’ Cyclic Feature in “R-SMS-Phos”
  作者：Borut Zupančič、Barbara Mohar、Michel Stephan

  DOI：10.1021/ol101029s

  日期：2010.7.2

  A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ee's also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.
• BOZELL, JOSEPH J.;VOGT, C. E.;GOZUM, J., J. ORG. CHEM., 56,(1991) N, C. 2584-2587
  作者：BOZELL, JOSEPH J.、VOGT, C. E.、GOZUM, J.

  DOI：——

  日期：——