tert-butyl 2-(naphthalen-1-yl)-2-oxoacetate | 1159628-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 2-(naphthalen-1-yl)-2-oxoacetate
• 英文别名: Tert-butyl 2-naphthalen-1-yl-2-oxoacetate；tert-butyl 2-naphthalen-1-yl-2-oxoacetate
• CAS: 1159628-73-5
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: HDDNCTFTHQFQHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(naphthalen-1-yl)-2-oxoacetate 在 三氟乙酸 作用下， 反应 2.5h， 生成 1-萘甲酰基甲酸
  参考文献：
  名称：

  Diastereodivergent Addition of Allenylzincs to Aryl Glyoxylates

  摘要：

  A diastereodivergent addition of allenylzincs to aryl glyoxylates was observed depending on the method used for the preparation of the allenylzinc reagent. The allenylzincs were prepared from propargylic benzoates in the presence of a palladium catalyst or by metalation of alkynes.

  DOI：

  10.1021/ol900494g
• 作为产物：
  描述：

  叔丁基过氧化氢 、 1-naphthylglyoxal 在 四氢吡咯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以93%的产率得到tert-butyl 2-(naphthalen-1-yl)-2-oxoacetate
  参考文献：
  名称：

  室温下 2-氧代醛/2-氧代亚胺离子和氢过氧化物的 2-氧代驱动偶联反应

  摘要：

  已开发出一种有效的 2-氧代基促进的 2-氧代醛和氢过氧化物之间的直接偶联反应。该方法已成功用于生成不同的 2-氧代酯和酸。该反应利用氢过氧化物的氢键诱导自分解趋势；该过程产生的中间体然后通过直接偶联或胺催化途径攻击醛或亚胺离子以产生交叉偶联产物。我们的方法不需要外部氧化剂或金属催化剂，反应在室温下进行。

  DOI：

  10.1002/ejoc.201600795

文献信息

• Asymmetric Reaction of α-Diazomethylphosphonates with α-Ketoesters To Access Optically Active α-Diazo-β-hydroxyphosphonate Derivatives
  作者：Fei Du、Jiao Zhou、Yungui Peng

  DOI：10.1021/acs.orglett.7b00128

  日期：2017.3.17

  The first example for asymmetric reaction of diazomethylphosphonates with α-ketoesters was realized in the catalysis of hydroquinidine-derived bifunctional thiourea. A methodology was established to access a series of chiral α-diazo-β-hydroxyphosphonate derivatives containing various functional groups with high enantioselectivities and yields. The resulting products could be further transformed into

  重氮基甲基膦酸酯与α-酮酸酯不对称反应的第一个实例是在对苯二酚衍生的双官能硫脲的催化中实现的。建立了一种方法，以获取一系列具有高对映选择性和高收率的，包含各种官能团的手性α-重氮-β-羟基膦酸酯衍生物。所得产物可进一步转化为手性叔β-羟基膦酸酯和α-卤代磷霉素衍生物，尤其是α-氟化物类似物。
• The effect of benzyl amine on the efficiency of the base-catalyzed transamination of α-keto esters
  作者：Fazhen Xue、Xiao Xiao、Haining Wang、Yian Shi

  DOI：10.1016/j.tet.2012.06.023

  日期：2012.8

  This paper describes the effect of benzyl amine on the base-catalyzed transamination of alpha-keto esters. Among various benzyl amines examined, o-HOC6H4CH2NH2 was found to be highly effective for the reaction, affording a wide variety of alpha-amino esters in good yields. The o-OH group of the benzyl amine facilitates the transamination process likely via H-bond. Moderate enantiomeric excess was obtained for alpha-amino ester when a quinine derived catalyst was used. (C) 2012 Elsevier Ltd. All rights reserved.
• Diastereodivergent Addition of Allenylzincs to Aryl Glyoxylates
  作者：Thomas Hameury、Jérôme Guillemont、Luc Van Hijfte、Véronique Bellosta、Janine Cossy

  DOI：10.1021/ol900494g

  日期：2009.6.4

  A diastereodivergent addition of allenylzincs to aryl glyoxylates was observed depending on the method used for the preparation of the allenylzinc reagent. The allenylzincs were prepared from propargylic benzoates in the presence of a palladium catalyst or by metalation of alkynes.
• 2-Oxo-Driven Coupling Reactions of 2-Oxo Aldehydes/2-Oxo Iminium Ions and Hydroperoxides at Room Temperature
  作者：Shahnawaz Khan、Qazi Naveed Ahmed

  DOI：10.1002/ejoc.201600795

  日期：2016.11

  2-oxo-group-promoted direct coupling reaction between 2-oxo aldehydes and hydroperoxides has been developed. The method has been used successfully for the generation of different 2-oxo esters and acids. This reaction harnesses the hydrogen-bonding-induced self-decomposition tendency of hydroperoxides; the intermediates produced by this process then attack the aldehyde or iminium ion to generate cross-coupled

  已开发出一种有效的 2-氧代基促进的 2-氧代醛和氢过氧化物之间的直接偶联反应。该方法已成功用于生成不同的 2-氧代酯和酸。该反应利用氢过氧化物的氢键诱导自分解趋势；该过程产生的中间体然后通过直接偶联或胺催化途径攻击醛或亚胺离子以产生交叉偶联产物。我们的方法不需要外部氧化剂或金属催化剂，反应在室温下进行。