3-[(carbobenzyloxy)aminophenylmethyl]-2,4-pentanedione | 878197-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(carbobenzyloxy)aminophenylmethyl]-2,4-pentanedione
• 英文别名: benzyl N-(2-acetyl-3-oxo-1-phenylbutyl)carbamate
• CAS: 878197-21-8
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: SVMVHPDNIYLTAF-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  523.3±50.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰丙酮 、 [phenyl-(toluene-4-sulfonyl)-methyl]-carbamic acid benzyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.83h， 以94%的产率得到3-[(carbobenzyloxy)aminophenylmethyl]-2,4-pentanedione
  参考文献：
  名称：

  无溶剂DBU促进的α-酰胺基对甲苯基砜与氟代丙二酸二乙酯和丙二酸二乙酯的曼尼希型反应

  摘要：

  已经开发出α-酰胺基对甲苯基砜与氟丙二酸二乙酯和丙二酸二乙酯分别在催化量的DBU存在下的曼尼希型反应。由芳族和脂族醛制得的各种α-酰胺基对甲苯砜分别在温和的反应条件下与氟代丙二酸二乙酯和丙二酸二乙酯反应，以中等至良好的收率得到α-氟代β-氨基酯和β-氨基酯。

  DOI：

  10.1016/j.tet.2010.05.075

文献信息

• Highly Practical BINOL-Derived Acid-Base Combined Salt Catalysts for the Asymmetric Direct Mannich-Type Reaction
  作者：Kazuaki Ishihara、Manabu Hatano

  DOI：10.1055/s-0030-1258296

  日期：2010.11

  salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1′-binaphthyl-2,2′-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction

  亚胺和1，3-二羰基化合物之间的催化不对称直接曼尼希型反应是有机化学中最重要的碳-碳键形成反应之一。所得的曼尼希加合物可以有效地转化为药学上有用的旋光性β-氨基酮，β-氨基酯，β-内酰胺等。在我们研究用于不对称反应的手性酸-碱结合盐催化剂的过程中，我们开发了一系列简单，实用的手性BINOL衍生的盐催化剂，例如手性吡啶鎓1,1'-联萘-2,2'-二磺酸盐1，手性联萘甲酸锂（I）2，手性联萘甲酸镁（II）（3） ，手性磷酸钙（II）4和手性磷酸5，对直接曼尼希型反应特别有效。 1引言 2 1,1'-联萘-2,2'-二磺酸（BINSA）-吡啶鎓盐 3萘甲酸锂（I）盐 4萘甲酸镁（II）盐 5磷酸钙（II）盐和手性磷酸 6。结论 酸碱复合盐催化剂-亚胺-不对称催化-1,3-二羰基化合物-直接曼尼希型反应
• Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts
  作者：Alessandra Puglisi、Maurizio Benaglia、Rita Annunziata、Davide Rossi

  DOI：10.1016/j.tetasy.2008.09.030

  日期：2008.10

  such bifunctional chiral molecules, either neutral or protonated species, was investigated in the addition of acetylacetone to β-nitrostyrene as a model reaction. Using the best conditions, high yields and enantioselectivities of up to 85% were obtained. The same metal free catalysts were then employed in the addition of activated nucleophiles to imines: in the reaction of 1,3-diketones with N-CBz imines

  通过（S）-t-亮氨酸衍生物与（1 R，2 R）-反式结合获得的新手性双功能有机催化剂的合成开发了-1，2-二氨基-环己烷。已经成功地合成了几种化合物，它们代表通过手性主链连接的含有硫脲基和叔氨基的一类有机催化剂。在模型反应中，向β-硝基苯乙烯中添加了乙酰丙酮，研究了这种中性或质子化双功能手性分子的催化行为。在最佳条件下，可获得高达85％的高收率和对映选择性。然后将相同的不含金属的催化剂用于向亚胺中添加活化的亲核试剂：在1,3-二酮与N -CBz亚胺的反应中，分离出的产物的收率高达61％ee，而与丙二酸二乙酯的反应则被分离出来。对映选择性高达71％。
• Hybrid Inorganic-Organic Materials Carrying Tertiary Amine and Thiourea Residues Tethered on Mesoporous Silica Nanoparticles: Synthesis, Characterization, and Co-Operative Catalysis
  作者：Alessandra Puglisi、Rita Annunziata、Maurizio Benaglia、Franco Cozzi、Antonella Gervasini、Vittorio Bertacche、Maria Chiara Sala

  DOI：10.1002/adsc.200800635

  日期：2009.1

  2-nitrostyrene, a reaction that under solvent-free conditions occurred in quantitative yield. By carrying out several experiments with the bifunctional catalysts featuring different molar ratios of active sites, and with different combinations of monofunctional supported and non-supported catalyst, the co-operativity of the tertiary amine and thiourea residues in catalyzing the reaction was demonstrated. The

  通过共缩聚法合成了具有不同负载量的叔胺和硫脲残基（残基比率分别为53 / 47、68 / 32和22/78）的介孔二氧化硅纳米粒子，并通过CP MAS NMR，粉末XRD，SEM对其进行了全面表征，BET，BJH和FT-IR技术。在将乙酰丙酮共轭添加到2-硝基苯乙烯中时，将这些材料作为双功能催化剂进行了测试，该反应在无溶剂条件下以定量收率进行。通过使用具有不同活性位摩尔比的双功能催化剂，以及单官能负载型和非负载型催化剂的不同组合进行几个实验，证明了叔胺和硫脲残基在催化反应中的协同作用。双功能催化剂的用途扩展到向活化的亚胺中添加乙酰丙酮。证明了总共三个反应循环的催化剂再循环，没有显着降低活性。
• PROCESS FOR MANUFACTURING DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALST, PROCESS FOR MANUFACTURING BETA-AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE
  申请人：Ishihara Kazuaki

  公开号：US20100249431A1

  公开（公告）日：2010-09-30

  Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1′-binaphthyl-2,2′-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80° C. for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1′-binaphthyl-2,2′-disulfonate. The (R)-1,1′-binaphthyl-2,2′-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH 2 Cl 2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0° C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0° C. for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.