methyl 2-diazo-3,7-dioxo-5,7-diphenylheptanoate | 1020183-41-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl 2-diazo-3,7-dioxo-5,7-diphenylheptanoate
• CAS: 1020183-41-8
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: XBOFITNEPNXOKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-diazo-3,7-dioxo-5,7-diphenylheptanoate 在 dirhodium(II) tetrakis(perfluorobutyrate) 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以66%的产率得到methyl 2-hydroxy-4-(2-oxo-2-phenylethyl)-3,4-dihydronaphthalene-1-carboxylate
  参考文献：
  名称：

  由 α,β-不饱和酮制备的重氮乙酰乙酸酯在二铑 (II) 催化反应中的化学选择性

  摘要：

  来自三氟甲磺酸锌的α-重氮β-酮酯催化α,β不饱和酮和α-甲硅烷氧基乙烯基重氮乙酸酯之间的Mukaiyama-Michael反应是合成可通过催化重氮分解获得的化合物的有价值的合成子。两组涉及 CH 插入和芳香族取代的例子证明了这种方法的多功能性。

  DOI：

  10.3998/ark.5550190.0011.803
• 作为产物：
  描述：

  苯甲醛 在 三乙烯二胺 、 sodium hydride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 methyl 2-diazo-3,7-dioxo-5,7-diphenylheptanoate
  参考文献：
  名称：

  Diazoacetoacetate Enones for the Synthesis of Diverse Natural Product-like Scaffolds

  摘要：

  Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, delta-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.

  DOI：

  10.1021/ol4015199

文献信息

• Construction of Highly Functionalized Diazoacetoacetates via Catalytic Mukaiyama−Michael Reactions
  作者：Yu Liu、Yu Zhang、Noel Jee、Michael P. Doyle

  DOI：10.1021/ol800298n

  日期：2008.4.1

  Functionalized diazo acelloacetates are prepared by an efficient Mukaiyama-Michael reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3-butenoate and alpha,beta-unsaturated enones. Vinyl ether and ketone derivatives are both accessible in good to excellent yield through this methodology. The mild Lewis acid zinc(II) triflate is the optimal catalyst, and its loading can be as low as 0.1 mol %. In addition, zinc triflate was also found to be a superior catalyst for the related Mukaiyama-aldol reaction.
• Divergent Stereocontrol of Acid Catalyzed Intramolecular Aldol Reactions of 2,3,7-Triketoesters: Synthesis of Highly Functionalized Cyclopentanones
  作者：Phong Truong、Charles S. Shanahan、Michael P. Doyle

  DOI：10.1021/ol301317a

  日期：2012.7.20

  The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from zeta-keto-alpha-diazo-beta-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Bronsted acid catalysis produces the corresponding 1,2-syn diastereomer.