1-benzoyl-2(S)-isopropyl-6(S)-carboxy-perhydropyrimidin-4-one | 211686-52-1

• 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: 1-benzoyl-2(S)-isopropyl-6(S)-carboxy-perhydropyrimidin-4-one
• 英文别名: 1-benzoyl-(2S)-isopropyl-(6S)-carboxyperhydropyrimidin-4-one；1-benzoyl-2(S)-isopropyl-6(S)-carboxyperhydropyrimidin-4-one；(2S,4S)-3-benzoyl-6-oxo-2-propan-2-yl-1,3-diazinane-4-carboxylic acid
• CAS: 211686-52-1
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: XBTULABWSKKTRI-AAEUAGOBSA-N

物化性质

• 熔点：
  175-177 °C
• 沸点：
  571.6±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzoyl-2(S)-isopropyl-6(S)-carboxy-perhydropyrimidin-4-one 在 palladium dichloride copper(l) iodide 、 碘苯二乙酸 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 1-benzoyl-2(S)-isopropyl-5-(3-hydroxy-prop-1-ynyl)-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  α-取代的β-氨基酸的对映选择性合成中Sonogashira偶联反应的合成2-取代的5-卤代-2,3-二氢-4，（H）-嘧啶-4-酮及其衍生物

  摘要：

  通过串联脱羧/β-碘化反应合成1-苯甲酰基-2（S）-取代的5-碘-2-，3-二氢-4（H）-嘧啶-4-酮的一种便捷的一锅法开发了相应的6-羧基-全氢嘧啶-4-酮。另外，通过将1-苯甲酰基-2（S）-溴化，可以容易地制备几个1-苯甲酰基-2（S）-取代的5-溴-2,3-二氢-4（H）-嘧啶-4-酮。取代的2，3-二氢-4（H）-嘧啶-4-酮。随后，将卤代杂环烯酮与各种末端炔烃进行Sonogashira偶联，制得1-苯甲酰基-2（S）-异丙基-5-炔基-2,3-二氢-4（H）-嘧啶-4-酮，收率高。将Sonogashira产品中的不饱和C-C部分进行氢化，然后进行酸水解，即可得到高度对映体富集的α-取代的β-氨基酸。

  DOI：

  10.1021/jo0705115
• 作为产物：
  描述：

  、 苯甲酰氯 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 1-benzoyl-2(S)-isopropyl-6(S)-carboxy-perhydropyrimidin-4-one
  参考文献：
  名称：

  (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones 通过 Suzuki-Miyaura 交叉偶联反应使用芳基三氟硼酸盐的功能化：方便的对映选择性制备 α-取代的 β-氨基酸

  摘要：

  Pd(OAc) 2 催化的 1-苯甲酰基-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones 与芳基三氟硼酸钾交叉偶联反应的简单方案已开发。该反应在 110 °C 下使用无配体催化剂进行。在所有情况下，观察到 1-苯甲酰基-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones 和芳基三氟硼酸盐完全转化为 CC 偶联产物在 30- 360 分钟 值得注意的是，芳基三氟硼酸钾中存在的多种基团（-CF 3 、-OMe、-SEt、-CN、-CHO、-Cl、-Cbz、-NCbz、-OH、-CO 2 H）可能是容忍。Suzuki-Miyaura 产品中的环内双键氢化，然后酸水解，得到高度对映体富集的 α-芳基取代的 β-氨基酸。

  DOI：

  10.1002/ejoc.201000852

文献信息

• Preparation of both enantiomers of β2-(3,4-dihydroxybenzyl)-β-alanine, higher homologues of Dopa
  作者：Claudia G. Avila-Ortiz、Gloria Reyes-Rangel、Eusebio Juaristi

  DOI：10.1016/j.tet.2005.06.094

  日期：2005.8

  and the desired β-amino acids were purified by silica gel chromatography. Alternatively, enantioenriched (R)- and (S)-1 were prepared by means of the highly diastereoselective alkylation (3,4-dimethoxybenzyl iodide) of open-chain β-aminopropionic acid derivatives (R,R,S)-8 and (S,S,R)-8 containing the chiral auxiliary α-phenylethylamine. Finally, nearly enantiopure (R)- and (S)-1 were obtained by resolution

  β 2 - （3,4-二羟基苄基）-β-丙氨酸[β 2 -Homo多巴，1 ]是一种新型的β氨基酸多巴，在帕金森氏病的治疗中最成功的治疗剂的同源物。通过对映纯的β-丙氨酸手性衍生物对映体纯嘧啶酮（R）-和（S）-3的非对映选择性烷基化，与藜芦基碘化物得到对映体富集的（R）-1和（S）-1。主要的非对映异构产物（2 S，5 R）-4和（2 R，5 S）-4将其用57％HBr水解，并通过硅胶色谱法纯化所需的β-氨基酸。或者，通过开链β-氨基丙酸衍生物（R，R，S）-8和（R）的高度非对映选择性烷基化（3,4-二甲氧基苄基碘）制备对映体富集的（R）-和（S）-1。S，S，R）-8包含手性辅助α-苯基乙胺。最后，通过外消旋N的拆分获得了近对映纯（R）-和（S）-1。-苄氧基羰基-2-（3，4-二苄氧基苄基）-3-氨基丙酸rac - 12，与（R）-或（S）-α-苯基乙胺，然后催化氢解。
• α-Alkylation of (<i>S</i>)-Asparagine with Self-Regeneration of the Stereogenic Center:  Enantioselective Synthesis of α-Substituted Aspartic Acids¹^,²
  作者：Eusebio Juaristi、Heraclio López-Ruiz、Domingo Madrigal、Yara Ramírez-Quirós、Jaime Escalante

  DOI：10.1021/jo980367a

  日期：1998.7.1

  A convenient method for the alpha-alkylation of (S)-asparagine with "self-regeneration of the stereogenic center" is described. The synthetic protocol involves stereoselective conversion of (S)-asparagine into enantiopure imino ether (2S,6S)-9, which is then alkylated with complete diastereoselectivity to give trans products 10-13 in good yields. Hydrolysis of these alkylated heterocycles is accomplished under mild acidic conditions to give the desired, enantiopure alpha-alkyl aspartic acids in excellent yields.
• Functionalization of 2-(S)-isopropyl-5-iodo-pyrimidin-4-ones through Cu(I)-mediated 1,3-dipolar azide–alkyne cycloadditions
  作者：Hélio A. Stefani、Mônica F.Z.J. Amaral、Flávia Manarin、Rômulo A. Ando、Nathália C.S. Silva、Eusebio Juaristi

  DOI：10.1016/j.tetlet.2011.10.011

  日期：2011.12

  A series of 2-(S)-isopropyl-pyrimidinones functionalized at C5 with triazole rings, in which the substituents are found at N-1' of the triazole ring, were synthesized. Through the azide-acetylene cycloaddition reaction, using Cul as a copper source and ultrasonic waves as an energy source it was possible to obtain products with yields ranging from 79% to 89% within 5 min or less. A preliminary study to gain further insight into the reaction was performed using in situ ReactIR technology. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of (2S)-isopropyl-5-alkynylpyrimidin-2-ones: precursors of β-aminoacids
  作者：Hélio A. Stefani、Monica F.Z.J. Amaral、Eusebio Juaristi

  DOI：10.1016/j.tetlet.2010.12.087

  日期：2011.3

  The efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one with, arylethynyl-, heteroarylethynyl-, and alkylethynyltrifluoroborate salts is reported. The standard protocol was evaluated and optimized in order to gain access to suitable precursors of enantiopure 2-substituted beta-amino acids. The scope and limitations of this methodology are discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• X-ray Crystallographic Study of Substituted Perhydropyrimidinones. Extreme Changes in Ring Conformation
  作者：Yara Ramírez-Quirós、Margarita Balderas、Jaime Escalante、Delia Quintana、Itzell Gallardo、Domingo Madrigal、Elies Molins、Eusebio Juaristi

  DOI：10.1021/jo991297q

  日期：1999.11.1

  X-ray crystal structures of 20 differently substituted perhydropyrimidin-4-ones are presented. Analysis of these data reveal a remarkable conformational sensitivity of a six-membered ring to substitution. Thus half-chair; envelope, boat, twist-boat, and intermediate conformations are found for the six-membered heterocycle, providing evidence for a relatively flat conformational energy surface in this ring, interpretation of the preferred conformations is advanced in terms of steric interactions among substituents and, in some cases, as the result of particular conformational (A(1,3) strain, anomeric) effects.