ethyl (R)-4-methyl-3-acetamidopentanoate | 343971-07-3

• 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: ethyl (R)-4-methyl-3-acetamidopentanoate
• 英文别名: ethyl (3R)-3-acetamido-4-methylpentanoate
• CAS: 343971-07-3
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: JECBJUZXFXBODH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (R)-4-methyl-3-acetamidopentanoate 在 盐酸 作用下， 反应 1.0h， 生成 (3S)-3-amino-4-methylpentanoic acid
  参考文献：
  名称：

  Preparation of highly enantiopure β-amino esters by Candida antarctica lipase A

  摘要：

  The enantioselectivities for the reactions of aliphatic beta -substituted beta -amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E=70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00002-7
• 作为产物：
  描述：

  3-乙酰氨基-4-甲基戊-2-烯酸乙酯 在 [Rh(1,1'-bis(2,4-diethylphosphetanyl)ferrocene)(MeOH)2]BF₄ 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 生成 ethyl (R)-4-methyl-3-acetamidopentanoate
  参考文献：
  名称：

  β-芳基取代的β-酰基氨基丙烯酸酯的制备和不对称氢化。

  摘要：

  DOI：

  10.1002/anie.200390242

文献信息

• C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
  申请人：Bao Jian

  公开号：US20050228190A1

  公开（公告）日：2005-10-13

  Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C 1 -symmetric bisphosphine ligands bound to transition metals.

  通过对原生手性烯烃进行对映选择性加氢制备(S)-(+)-3-(氨甲基)-5-甲基己酸及其结构相关化合物的材料和方法已被披露。这些方法采用了新颖的手性催化剂，其中包括与过渡金属结合的C1对称双膦配体。
• A Highly Tunable Family of Chiral Bisphospholanes for Rh-Catalyzed Enantioselective Hydrogenation Reactions
  作者：Jens Holz、Odalys Zayas、Haijun Jiao、Wolfgang Baumann、Anke Spannenberg、Axel Monsees、Thomas H. Riermeier、Juan Almena、Renat Kadyrov、Armin Börner

  DOI：10.1002/chem.200600033

  日期：2006.6.23

  enantioselectivities in methanol as the solvent. This may account for optimised steric and electronic effects. However, by changing the solvent catalysts with other backbones can give rise to excellent results. This gives proof that simple correlations between steric and electronic properties and results in the enantioselective hydrogenation frequently claimed in literature are not general.

  通过使用高度灵活和收敛的方法，已经制备了一组16种新的且密切相关的双膦环烷配体。每种合成可以在工业上相关的规模上进行。双膦在连接两个膦酸酯单元的桥的性质上不同。桥由三元，四元，五元和六元杂环或脂环族环形成。通过使用理论计算（DFT）和分析测量结果（（31）P和（103）Rh NMR光谱，X射线结构分析）研究了双膦酮及其Rh预催化剂。研究表明，基于具有马来酸酐或马来酰亚胺桥的配体的催化剂在甲醇作为溶剂中具有不断优异的对映选择性。这可以说明优化的空间和电子效果。然而，通过改变溶剂催化剂与其他主链可以产生优异的结果。这证明了在空间性质和电子性质之间的简单关联以及导致文献中经常要求的对映选择性氢化的结果并不普遍。
• Highly Enantioselective Rhodium-Catalyzed Hydrogenation of β-Dehydroamino Acid Derivatives Using Monodentate Phosphoramidites
  作者：Diego Peña、Adriaan J. Minnaard、Johannes G. de Vries、Ben L. Feringa

  DOI：10.1021/ja028235t

  日期：2002.12.1

  monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-beta-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems were established for (E)-beta-(acylamino)acrylates (98-99% ee) and (Z)-beta-(acylamino)acrylates (92-95% ee) based on phosphoramidites

  已开发出新的且非常容易获得的单齿亚磷酰胺配体，其在具有脂肪族和芳香族侧链的 (E)- 和 (Z)-β-脱氢氨基酸衍生物的氢化中产生出色的 ee 和完全转化。特别是，基于亚磷酰胺 2 和 3，为 (E)-β-(酰氨基)丙烯酸酯 (98-99% ee) 和 (Z)-β-(酰氨基) 丙烯酸酯 (92-95% ee) 建立了两种不同的催化体系， 分别。
• Application of a new amidophosphite ligand to Rh-catalyzed asymmetric hydrogenation of β-dehydroamino acid derivatives in supercritical carbon dioxide: Activation effect of protic co-solvents
  作者：Sergey E. Lyubimov、Eugenie A. Rastorguev、Vadim A. Davankov

  DOI：10.1002/chir.20992

  日期：2011.9

  New chiral amidophosphite ligand was synthesized and tested in the Rh‐catalyzed asymmetric hydrogenation of (Z)‐β‐(acylamino)acrylates in protic solvents and supercritical carbon dioxide (scCO2) The catalytic performance is affected greatly by the acidity of the solvents. Better enantioselectivity (up to 88% ee) was achieved in scCO2 containing 1,1,1,3,3,3‐hexafluoro‐2‐propanol, compared to neat protic

  在质子溶剂和超临界二氧化碳（scCO 2）中，对（Z）-β-（酰基氨基）丙烯酸酯进行Rh催化的不对称氢化反应，合成并测试了新的手性氨基亚磷酸酯配体。溶剂的酸度极大地影响了催化性能。与纯质子溶剂相比，含有1,1,1,1,3,3,3-六氟-2-丙醇的scCO 2具有更好的对映选择性（高达88％ee）。手性，2011年。©2011 Wiley‐Liss，Inc.。
• A Bulky Three-Hindered Quadrant Bisphosphine Ligand: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes
  作者：Yuuki Sawatsugawa、Ken Tamura、Natsuhiro Sano、Tsuneo Imamoto

  DOI：10.1021/acs.orglett.9b02702

  日期：2019.11.15

  quadrant bisphosphine ligand, di-1-adamantylphosphino(tert-butylmethylphosphino)methane, named BulkyP*, has been synthesized via a convergent short pathway with chromatography-free procedures. The ligand is a crystalline solid and can be readily handled in air. Its rhodium(I) complex exhibits very high enantioselectivities and catalytic activities in the asymmetric hydrogenation of functionalized alkenes

  庞大的三阻碍象限双膦配体，二-1-金刚烷基膦基（叔丁基甲基膦基）甲烷，称为BulkyP *，是通过收敛的短路径和无色谱方法合成的。配体是结晶固体，可以很容易地在空气中处理。它的铑（I）配合物在官能化烯烃的不对称氢化中表现出很高的对映选择性和催化活性。