methyl 4-(phenylamino)butanoate | 91246-76-3

• 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 4-(phenylamino)butanoate
• 英文别名: methyl 4-anilinobutanoate
• CAS: 91246-76-3
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: AKLLCCKTVZPGBX-UHFFFAOYSA-N

物化性质

• 沸点：
  322.5±25.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(phenylamino)butanoate 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-苯基-2-吡咯烷酮
  参考文献：
  名称：

  Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis ofN-Substituted Cyclic Amines

  摘要：

  硼烷-硫化甲基（BMS）还原各种N-取代的琥珀酰胺和戊二酰胺酯，可以高产率地得到相应的N-取代吡咯烷和哌啶。这一转化过程中，由于胺氮周围的空间阻碍限制，以及通过不完全反应和/或合成后续的BMS还原检测到的假定中间体，表明环化作用和酰胺还原成功地与酯还原竞争，从而得到了N-取代的环化胺。

  DOI：

  10.1055/s-1988-27777
• 作为产物：
  描述：

  N-(3-chloropropyl)aniline 在 盐酸 、 正丁基锂 、 4,4'-二叔丁基苯并 、 lithium 作用下， 反应 3.5h， 生成 methyl 4-(phenylamino)butanoate
  参考文献：
  名称：

  4,4′-Di-tert-butylbiphenyl-catalysed reductive opening of azetidines with lithium: A direct preparation of 3,N-dilithioalkylamines

  摘要：

  The reaction of N-phenylazetidine 1a with an excess of lithium powder and a catalytic amount of 4,4'-ditert-butylbiphenyl (5 mol %) in THF at -15 degrees C leads to the corresponding dianion 2a, which by treatment with different electrophiles (H2O, D2O, Bu(CHO, PhCHO, (CH2)(5)CO, PhCH=NPh, CO2) yields, after hydrolysis with mater, the expected functionalysed amines 3aa-ah. The same method applied to N-isopropyl-2-phenylazetidine Ic affords compounds 3ca-ce (electrophiles: H2O, D2O, PhCHO, Me(2)CO, CH2=CHCH2Br) resulting from the more stable benzylic intermediate 2c. Finally, the regiochemistry in the reductive opening of 2-methyl-N-phenylazetidine Id followed by deuterolysis was studied: a mixture of both regioisomers 3da+3da' was obtained, the ratio being the oposite as expected according to the stability of both intermediates 2d and 2d'.

  DOI：

  10.1016/s0040-4020(01)85645-3

文献信息

• Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins
  作者：Anthony Millet、Quentin Lefebvre、Magnus Rueping

  DOI：10.1002/chem.201602257

  日期：2016.9.12

  A tin‐ and halide‐free, visible‐light photoredox‐catalyzed Giese reaction was developed. Primary and secondary α‐amino radicals were generated readily from amino acids in the presence of catalytic amounts of an iridium photocatalyst. The reactivity of the α‐amino radicals has been evaluated for the functionalization of a variety of activated olefins.

  开发了一种无锡和无卤可见光氧化还原催化的Giese反应。在催化量的铱光催化剂存在下，氨基酸很容易产生伯和仲α-氨基。已经评估了α-氨基自由基的反应性，以用于各种活化烯烃的功能化。
• Enantioconvergent photoredox radical-radical coupling catalyzed by a chiral-at-rhodium complex
  作者：Zijun Zhou、Xin Nie、Klaus Harms、Radostan Riedel、Lilu Zhang、Eric Meggers

  DOI：10.1007/s11426-019-9584-x

  日期：2019.11

  support a mechanism which is initiated by a single electron transfer from N-aryl glycinate to the photochemically excited rhodium-bound α-chloro imidazol-2-yl-ketone, followed by chloride fragmentation of the α-chloroketone, decarboxylation of the glycinate, and a subsequent highly stereocontrolled radical-radical coupling. This work showcases the ability of the chiral rhodium catalyst to serve a dual function

  外消旋α-氯咪唑-2-基酮通过单双环金属化铑手性催化剂催化与N-芳基甘氨酸的对映体光活化CC键形成对映体过量（ee）。对照实验支持一种机制，该机制是由N的单次电子转移引发的甘氨酸-芳基乙酸酯与光化学激发的铑键合的α-氯咪唑-2-基-酮，随后是α-氯酮的氯化物断裂，甘氨酸的脱羧，以及随后的高度立体控制的自由基-自由基偶联。这项工作展示了手性铑催化剂既具有手性路易斯酸的双重功能，又具有与底物结合时的光氧化还原活性物质的双重功能。
• Class of HDAC inhibitors expands the renal progenitor cells population and improves the rate of recovery from acute kidney injury
  申请人：Day Billy W.

  公开号：US10160705B2

  公开（公告）日：2018-12-25

  Compounds and compositions are provided that inhibit histone deacylase activity and which expand renal progenitor cell populations and improve kidney function in a damaged kidney. Methods of use of the compounds and compositions are provided.

  本研究提供了抑制组蛋白脱乙酰酶活性的化合物和组合物，这些化合物和组合物能扩大肾脏祖细胞群，改善受损肾脏的肾功能。还提供了使用这些化合物和组合物的方法。
• Visible‐Light‐Induced Synthesis of γ‐Amino Sulfones from Vinyl Sulfones and Amino Acids
  作者：Zhu‐Ming Qian、Feng‐Yu Wang、Zhi Guan、Yan‐Hong He

  DOI：10.1002/adsc.202400432

  日期：2024.7.2

  A method for the synthesis of γ‐amino sulfones through visible light‐induced oxidative decarboxylation and radical reductive addition is described. Various readily available N‐protected natural amino acids react with aromatic/aliphatic vinyl sulfones to directly produce γ‐amino sulfone derivatives. This reaction is also applicable to α‐N(O)‐acids and other aliphatic carboxylic acids, resulting in the

  描述了一种通过可见光诱导的氧化脱羧和自由基还原加成合成γ-氨基砜的方法。各种容易获得的N-保护的天然氨基酸与芳香族/脂肪族乙烯基砜反应直接生成γ-氨基砜衍生物。该反应也适用于α-N(O)-酸和其他脂肪族羧酸，产生相应的砜衍生物。该方法无需牺牲还原剂或额外的氢原子供体即可进行。唯一的副产品是脱羧释放的二氧化碳，使该过程既原子又经济。
• Class of HDAC Inhibitors Expands the Renal Progenitor Cells Population and Improves the Rate of Recovery from Acute Kidney Injury
  申请人：University of Pittsburgh - Of the Commonwealth System of Higher Education

  公开号：US20180312455A1

  公开（公告）日：2018-11-01

  Compounds and compositions are provided that inhibit histone deacylase activity and which expand renal progenitor cell populations and improve kidney function in a damaged kidney. Methods of use of the compounds and compositions are provided.