(E)-2-<(4-morpholinylcarbonyl)methyl>-trans-cinnamic acid | 116129-75-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-<(4-morpholinylcarbonyl)methyl>-trans-cinnamic acid
• 英文别名: (E)-2-benzylidene-3-(morpholinocarbonyl)propionic acid；(E)-2-[(4-morpholinylcarbonyl)methyl]-trans-cinnamic acid；(2E)-2-benzylidene-4-morpholin-4-yl-4-oxobutanoic acid
• CAS: 116129-75-0
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: YXLWOASJILPHLE-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-<(4-morpholinylcarbonyl)methyl>-trans-cinnamic acid 在 [Rh((R,R)-iPr-JDayPhos)(MeOH)₂]BF₄ 、 氢气 作用下， 以 甲醇 为溶剂， 22.0 ℃ 、300.01 kPa 条件下， 反应 0.08h， 以98%的产率得到
  参考文献：
  名称：

  1,1'-二茂铁基核心的P-Stereogenic二膦酸酯模块：''JDayPhos''系列及其在铑（I）催化加氢中的应用

  摘要：

  开发了一种新型的基于二茂铁的P-立体异构二膦配体系列JDayPhos，该化合物的一些成员的铑（I）配合物表现出出色的对映选择性（高达> 99％ee），并且在β-未取代或-β的不对称氢化中表现出高活性。取代的衣康酸酯和α-亚甲基-γ-氧代羧酸酯。

  DOI：

  10.1002/adsc.201800255
• 作为产物：
  描述：

  (E)-4-phenyl-3-carbethoxyethylbut-3-enoic acid 在 N-甲基吗啉 、 lithium hydroxide 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.25h， 生成 (E)-2-<(4-morpholinylcarbonyl)methyl>-trans-cinnamic acid
  参考文献：
  名称：

  Renin inhibitors. Dipeptide analogs of angiotensinogen utilizing a structurally modified phenylalanine residue to impart proteolytic stability

  摘要：

  A series of renin inhibitors have been prepared and evaluated for their susceptibility to cleavage by the serine protease chymotrypsin. The compounds were designed by consideration of the structural requirements in the active-site region of renin and chymotrypsin. By systematic alteration of the P3 phenylalanine residue, compounds with varying degrees of renin inhibitory potency and chymotrypsin susceptibility were obtained. Selected analogues from this group were examined in vivo for both their hypotensive effects and metabolic patterns.

  DOI：

  10.1021/jm00120a006

文献信息

• Chiral 1,1′-Diphosphetanylferrocenes: New Ligands for Asymmetric Catalytic Hydrogenation of Itaconate Derivatives
  作者：Ulrich Berens、Mark J. Burk、Arne Gerlach、William Hems

  DOI：10.1002/1521-3773(20000602)39:11<1981::aid-anie1981>3.0.co;2-3

  日期：2000.6.2
• Renin inhibitors. Dipeptide analogs of angiotensinogen utilizing a structurally modified phenylalanine residue to impart proteolytic stability
  作者：Jacob J. Plattner、Patrick A. Marcotte、Hollis D. Kleinert、Herman H. Stein、Jonathan Greer、Giorgio Bolis、Anthony K. L. Fung、Barbara A. Bopp、Jay R. Luly

  DOI：10.1021/jm00120a006

  日期：1988.12

  A series of renin inhibitors have been prepared and evaluated for their susceptibility to cleavage by the serine protease chymotrypsin. The compounds were designed by consideration of the structural requirements in the active-site region of renin and chymotrypsin. By systematic alteration of the P3 phenylalanine residue, compounds with varying degrees of renin inhibitory potency and chymotrypsin susceptibility were obtained. Selected analogues from this group were examined in vivo for both their hypotensive effects and metabolic patterns.
• Modular 1,1′-Ferrocenediyl-cored <i>P</i> -Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation
  作者：Gašper Poklukar、Michel Stephan、Barbara Mohar

  DOI：10.1002/adsc.201800255

  日期：2018.7.4

  A novel ferrocene‐based P‐stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β‐unsubstituted or ‐substituted itaconates and α‐methylene‐γ‐oxo‐carboxylates.

  开发了一种新型的基于二茂铁的P-立体异构二膦配体系列JDayPhos，该化合物的一些成员的铑（I）配合物表现出出色的对映选择性（高达> 99％ee），并且在β-未取代或-β的不对称氢化中表现出高活性。取代的衣康酸酯和α-亚甲基-γ-氧代羧酸酯。