1-benzoyl-2(S)-isopropyl-5-iodo-2,3-dihydro-1H-pyrimidin-4-one | 475983-77-8

• 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-5-iodo-2,3-dihydro-1H-pyrimidin-4-one
• 英文别名: (S)-1-benzoyl-5-iodo-2-isopropyl-2,3-dihydropyrimidin-4(1H)-one；1-benzoyl-5-iodo-(2S)-isopropyl-2,3-dihydro-4(H)-pyrimidin-4-one；1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one；(S)-1-benzoyl-2-isopropyl-5-iododihydropyrimidin-4-one；(2S)-3-benzoyl-5-iodo-2-propan-2-yl-1,2-dihydropyrimidin-6-one
• CAS: 475983-77-8
• 化学式: C₁₄H₁₅IN₂O₂
• 分子量: 370.19
• InChiKey: IJEQHZNEJYTWHH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoyl-2(S)-isopropyl-5-iodo-2,3-dihydro-1H-pyrimidin-4-one 在 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.58h， 生成 (S)-1-benzoyl-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-isopropyl-2,3-dihydropyrimidin-4(1H)-one
  参考文献：
  名称：

  Functionalization of 2-(S)-isopropyl-5-iodo-pyrimidin-4-ones through Cu(I)-mediated 1,3-dipolar azide–alkyne cycloadditions

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.10.011
• 作为产物：
  描述：

  1-benzoyl-2(S)-isopropyl-6(S)-carboxy-perhydropyrimidin-4-one 在 碘苯二乙酸 、 碘 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到1-benzoyl-2(S)-isopropyl-5-iodo-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

文献信息

• α-Arylation and Alkynylation of Cyclic α-Iodoenones Using Palladium-Catalyzed Cross-Coupling Reactions with Trifluoroborate Salts
  作者：Hélio Stefani、Kemilla Gueogjian、Fateh Singh、Jesus Pena、Monica Amaral

  DOI：10.1055/s-0029-1218580

  日期：2010.2

  An expeditious synthesis of α-aryl- and α-alkynylcyclohexenones is described and illustrated by palladium-catalyzed cross-coupling reaction of cyclic α-iodoenones with potassium aryl-trifluoroborate salts. This procedure offers easy access to α-arylated and alkynylated cyclohexenones functionalized with electrondonor and -acceptor substituents in good yields.

  通过钯催化的环状 α-碘代烯酮与芳基三氟硼酸钾盐的交叉偶联反应，描述并说明了 α-芳基-和 α-炔基环己烯酮的快速合成。该程序可以轻松获得用电子给体和受体取代基官能化的 α-芳基化和炔基化环己烯酮，收率良好。
• Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of α-Substituted β-Amino Acids
  作者：Hélio A. Stefani、Monica F. Z. J. Amaral、Gloria Reyes-Rangel、Jorge Vargas-Caporali、Eusebio Juaristi

  DOI：10.1002/ejoc.201000852

  日期：2010.11

  -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz, -OH, -CO 2 H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenriched α-aryl-substituted β-Amino acids.

  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。
• 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.
• Tandem reactions initiated by the oxidative decarboxylation of 1-benzoyl-2(S)-tert-butyl-6(S)-carboxyperhydropyrimidin-4-one
  作者：Martı́n A. Iglesias-Arteaga、C.Gabriela Avila-Ortiz、Eusebio Juaristi

  DOI：10.1016/s0040-4039(02)01066-3

  日期：2002.7

  Treatment of the title perhydropyrimidinone with diacetoxyiodobenzene and iodine followed by addition of allyltrimethylsilane and boron trifluoride etherate afforded 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(H)-pyrimidin-4-one in 65 71% yield, via an efficient three-step radical decarboxylation-oxidation-beta-elimination tandem reaction. In contrast, when addition of allyltrimethylsilane/BF3.OEt2, was suppressed, a remarkable five-step tandem process led to the formation of vinylic iodide, 1-benzoyl-2(S)-tertbutyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one as the main product. (C) 2002 Elsevier Science Ltd. All rights reserved.