ethyl 3-amino-5-methylhex-2-enoate | 99065-40-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-amino-5-methylhex-2-enoate
• CAS: 99065-40-4
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: RZDLVKJNKZTMKU-UHFFFAOYSA-N

物化性质

• 沸点：
  260.2±13.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-5-methylhex-2-enoate 在 [Rh((S,S)-Me-BDPMI)(COD))BF₄] 吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.36 kPa 条件下， 反应 36.0h， 生成 ethyl (S)-5-methyl-3-acetamidohexanoate
  参考文献：
  名称：

  Rh(I)-Catalyzed Enantioselective Hydrogenation of (E)- and (Z)-β-(Acylamino)acrylates Using 1,4-Bisphosphine Ligands under Mild Conditions

  摘要：

  [GRAPHICS]Rh-Me-BDPMI (1a) complex can be an effective catalyst for the hydrogenations of (E)- and (2)-beta-(acylamino)acrylates, in which the Zisomers hydrogenated with the same or even higher ee values than the corresponding E-isomers. The conversion yield and enantioselectivity of E-and Z-isomers were largely dependent on the solvent, and thus, the E-isomers were hydrogenated more effectively in CH2Cl2, whereas the Z-isomers were hydrogenated more effectively in polar MeOH solvent.

  DOI：

  10.1021/ol0261884
• 作为产物：
  描述：

  5-甲基-3-羰基己酸乙酯 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 ethyl 3-amino-5-methylhex-2-enoate
  参考文献：
  名称：

  Rh(I)-Catalyzed Enantioselective Hydrogenation of (E)- and (Z)-β-(Acylamino)acrylates Using 1,4-Bisphosphine Ligands under Mild Conditions

  摘要：

  [GRAPHICS]Rh-Me-BDPMI (1a) complex can be an effective catalyst for the hydrogenations of (E)- and (2)-beta-(acylamino)acrylates, in which the Zisomers hydrogenated with the same or even higher ee values than the corresponding E-isomers. The conversion yield and enantioselectivity of E-and Z-isomers were largely dependent on the solvent, and thus, the E-isomers were hydrogenated more effectively in CH2Cl2, whereas the Z-isomers were hydrogenated more effectively in polar MeOH solvent.

  DOI：

  10.1021/ol0261884

文献信息

• Iodine‐Promoted One‐pot Synthesis of Highly Substituted 4‐Aminopyrroles and Bis‐4‐aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines
  作者：Hitesh B. Jalani、Jyotirling R. Mali、Hyejun Park、Jae Kyun Lee、Kiho Lee、Kyeong Lee、Yongseok Choi

  DOI：10.1002/adsc.201800899

  日期：2018.11.5

  functionally diverse and highly substituted 4‐aminopyrroles directly from aryl methyl ketones, arylamines, and enamines was developed. The reaction involves in‐situ oxidation of aryl methyl ketone to glyoxal, subsequent imine formation by aniline, followed by nucleophilic addition of enamine, and cyclization to afford highly substituted 4‐aminopyrroles. This reaction involved the formation of two C−N

  直接由芳基甲基酮，芳基胺和烯胺开发了碘促进的一锅合成功能多样且高度取代的4-氨基吡咯。反应包括将芳基甲基酮原位氧化为乙二醛，随后通过苯胺形成亚胺，然后亲核加成烯胺，然后环化得到高度取代的4-氨基吡咯。该反应涉及通过正式的[1 + 1 + 3]环化方法形成两个C-N键和一个C-C键。本方法提供了一个有趣的框架，即通过4,4'-二酰基联苯，胺和烯胺基团的反应直接连接到联苯核上的两个4-氨基吡咯单元。这种Hantzsch型单锅反应可提供多种4-氨基吡咯，可用于药物/材料化学。
• Screening of a Novel Fragment Library with Functional Complexity against <i>Mycobacterium tuberculosis</i> InhA
  作者：Federica Prati、Fabio Zuccotto、Daniel Fletcher、Maire A. Convery、Raquel Fernandez-Menendez、Robert Bates、Lourdes Encinas、Jingkun Zeng、Chun-wa Chung、Paco De Dios Anton、Alfonso Mendoza-Losana、Claire Mackenzie、Simon R. Green、Margaret Huggett、David Barros、Paul G. Wyatt、Peter C. Ray

  DOI：10.1002/cmdc.201700774

  日期：2018.4.6

  benefits of including functional group complexity (FGC) within fragments when screening against protein targets such as Mycobacterium tuberculosis InhA. We show that InhA fragment actives with FGC maintained their binding pose during elaboration. Furthermore, weak fragment hits with functional group handles also allowed for facile fragment elaboration to afford novel and potent InhA inhibitors with good

  我们在此报告的研究结果为在筛选结核分枝杆菌InhA等蛋白质靶标时在片段中包含功能组复杂性 (FGC) 的好处提供了支持。我们表明 InhA 片段活性物质与 FGC 在精加工过程中保持其结合姿势。此外，功能组手柄的弱片段命中也允许轻松的片段精加工，以提供新颖且有效的 InhA 抑制剂，并具有良好的配体效率指标以进行优化。
• From Triazoles to Imidazolines through the Sequential N–H Insertion of α-Imino Rhodium–Carbenes into β-Enamino Esters/Enamine–Imine Tautomerization/Conjugate Addition Cascade
  作者：Hyun Ji Jeon、Da Jung Jung、Ju Hyun Kim、Youngmee Kim、Jean Bouffard、Sang-gi Lee

  DOI：10.1021/jo501785d

  日期：2014.10.17

  A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic beta-enamino esters affords 2,5-dihydro-H-1-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N-H insertion of an alpha-imino rhodium-carbene, followed by enamine-imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for alpha-substituted beta-enamino esters (R-3 = Me, Ph) to give a single diastereomer.
• Structure activity relationships of 4-hydroxy-2-pyridones: A novel class of antituberculosis agents
  作者：Pearly Shuyi Ng、Ujjini H. Manjunatha、Srinivasa P.S. Rao、Luis R. Camacho、Ngai Ling Ma、Maxime Herve、Christian G. Noble、Anne Goh、Stefan Peukert、Thierry T. Diagana、Paul W. Smith、Ravinder Reddy Kondreddi

  DOI：10.1016/j.ejmech.2015.10.008

  日期：2015.12

  Pyridone 1 was identified from a high-throughput cell-based phenotypic screen against Mycobacterium tuberculosis (Mtb) including multi-drug resistant tuberculosis (MDR-TB) as a novel anti-TB agent and subsequently optimized series using cell-based Mtb assay. Preliminary structure activity relationship on the isobutyl group with higher cycloalkyl groups at 6-position of pyridone ring has enabled us to significant improvement of potency against Mtb. The lead compound 30j, a dimethylcyclohexyl group on the 6-position of the pyridone, displayed desirable in vitro potency against both drug sensitive and multi-drug resistant TB clinical isolates. In addition, 30j displayed favorable oral pharmacokinetic properties and demonstrated in vivo efficacy in mouse model. These results emphasize the importance of 4-hydroxy-2-pyridones as a new chemotype and further optimization of properties to treat MDR-TB. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Lukes,R.; Kloubek,J., Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 607 - 609
  作者：Lukes,R.、Kloubek,J.

  DOI：——

  日期：——