ethyl 4-azido-2-diazo-5-hydroxy-3-oxo-5-phenylpentanoate | 599175-23-2

• 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 4-azido-2-diazo-5-hydroxy-3-oxo-5-phenylpentanoate
• 英文别名: Ethyl 4-azido-2-diazo-5-hydroxy-3-oxo-5-phenylpentanoate
• CAS: 599175-23-2
• 化学式: C₁₃H₁₃N₅O₄
• 分子量: 303.277
• InChiKey: CXGCSWWJXUDSDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-azido-2-diazo-5-hydroxy-3-oxo-5-phenylpentanoate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 ethyl anti-5-acetoxy-2-diazo-4-(dimethylphosphorylamino)-5-phenyl-3-oxopentanoate
  参考文献：
  名称：

  Synthesis of dimethylphosphorylamino diazo esters by a selective tandem Staudinger/Arbuzov rearrangement sequence of azido diazo esters with trimethylphosphite

  摘要：

  gamma-Azido-alpha-diazo-beta-keto esters react selectively with trimethylphosphite by a tandem Staudinger/Arbuzov rearrangement sequence, furnishing gamma-(dimethylphosphorylamino)-alpha-diazo-beta-keto esters in good yield under mild conditions. Collected X-ray data for the novel diazo phosphoramides confirm the proposed chemoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00856-1
• 作为产物：
  描述：

  哌啶乙酸盐 、 苯甲醛 、 ethyl 4-azido-2-diazo-3-oxobutanoate 以 乙醇 为溶剂， 反应 48.0h， 以30%的产率得到ethyl 4-azido-2-diazo-5-hydroxy-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Synthesis of dimethylphosphorylamino diazo esters by a selective tandem Staudinger/Arbuzov rearrangement sequence of azido diazo esters with trimethylphosphite

  摘要：

  gamma-Azido-alpha-diazo-beta-keto esters react selectively with trimethylphosphite by a tandem Staudinger/Arbuzov rearrangement sequence, furnishing gamma-(dimethylphosphorylamino)-alpha-diazo-beta-keto esters in good yield under mild conditions. Collected X-ray data for the novel diazo phosphoramides confirm the proposed chemoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00856-1

文献信息

• Metal substituted diazo esters as substrates for cross coupling reactions
  作者：Albert Padwa、Marcus M. Sá、M. David Weingarten

  DOI：10.1016/s0040-4020(96)01194-5

  日期：1997.2

  nucleophiles. The base-promoted reaction of ethyl 4-azido-2-diazo-3-oxo-butanoate with both acetaldehyde and benzaldehyde proceeded in high yield to produce mixed aldol products. The use of an equivalent amount of DABCO was found to be the best way to promote the reaction. The diastereoselectivity exhibited in the reaction is low and characteristic of condensations of α-substituted ketones with substituents

  （三烷基锡烷基）重氮乙酸乙酯已被用作Stille反应的底物。钯（0）催化的交叉偶联可与芳基碘化物很好地起作用，而与酰基或芳基氯化物不能很好地起作用。比斯-[[乙氧基羰基-重氮甲基]-汞显示出对溴乙酰溴的高反应活性，以优异的产率提供了4-溴-2-重氮-3-氧代-丁酸乙酯。该化合物用于与各种亲核试剂的取代反应。4-叠氮基-2-重氮-3-氧代丁酸乙酯与乙醛和苯甲醛的碱促进反应以高收率进行，以生产混合的醛醇产物。发现使用等量的DABCO是促进反应的最佳方法。反应中显示的非对映选择性低，并且α-取代的酮与在α-位的烷基以外的取代基缩合的特征。对于2-重氮-3-氧代-4-苯基丁酸乙酯与乙醛和苯甲醛的反应也发现了类似的结果。
• Synthesis of dimethylphosphorylamino diazo esters by a selective tandem Staudinger/Arbuzov rearrangement sequence of azido diazo esters with trimethylphosphite
  作者：Marcus M. Sá、Gustavo P. Silveira、Adailton J. Bortoluzzi、Albert Padwa

  DOI：10.1016/s0040-4020(03)00856-1

  日期：2003.7

  gamma-Azido-alpha-diazo-beta-keto esters react selectively with trimethylphosphite by a tandem Staudinger/Arbuzov rearrangement sequence, furnishing gamma-(dimethylphosphorylamino)-alpha-diazo-beta-keto esters in good yield under mild conditions. Collected X-ray data for the novel diazo phosphoramides confirm the proposed chemoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.