3-oxo-2-phenyl-acrylic acid methyl ester | 32084-13-2

• 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-oxo-2-phenyl-acrylic acid methyl ester
• 英文别名: 3-Oxo-2-phenyl-acrylsaeure-methylester；Methyl phenylketenecarboxylate
• CAS: 32084-13-2
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: PWPGFROVYQYOJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3-oxo-2-phenyl-acrylic acid methyl ester 生成 2,4-dioxo-1,3-diphenyl-cyclobutane-1,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Staudinger; Hirzel, Chemische Berichte, 1917, vol. 50, p. 1033

  摘要：

  DOI：
• 作为产物：
  描述：

  6-Methoxy-2,2-dimethyl-5-phenyl-1,3-dioxin-4-one 生成 3-oxo-2-phenyl-acrylic acid methyl ester
  参考文献：
  名称：

  生成α-氧杂环丁烯的有效方法：烯醇化的麦德鲁姆酸衍生物的环还原

  摘要：

  由Meldrum酸合成了一系列6-甲氧基-或甲硅烷氧基-4 H -1,3-二恶英-4-酮。这些二恶英在20–50°C下进行了4 + 2环还原，定量转化为甲氧基或甲硅烷氧基羰基酮和酮。通过红外光谱以及用叔丁醇捕获来表征烯酮。这些烯醇化的Meldrum酸衍生物的现成环还原反应强烈表明，Meldrum酸对亲核试剂的异常高敏感性是由于互变异构6-羟基二恶英酮的环还原反应所产生的羧基烯酮的参与。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01566-9

文献信息

• CAJANINE STRUCTURE ANALOGOUS COMPOUND, PREPARATION METHOD AND USE
  申请人：INSTITUTE OF MEDICINAL BIOTECHNOLOGY. CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20140371232A1

  公开（公告）日：2014-12-18

  Provided are cajanine structure analogous compounds, synthesis method and pharmacological effects thereof, the compounds of the present invention having the structure as represented by general formulas I, II, III, IV and V. Also provided are pharmaceutical compositions containing the compounds as active ingredient, and uses thereof; the compounds of the present invention having the pharmacological activities such as anti-virus, anti-virus-infection, nerve protection, anti-metabolic-diseases and the like. Also provided is a chemical total synthesis preparation method of the natural products cajanine, cajanine A and cajanine C. The present invention lays a foundation for the in-depth study and development of the compounds as clinical drugs in the future.

  提供的是与咖啡碱结构类似的化合物、合成方法及其药理效果，本发明的化合物具有如公式I、II、III、IV和V所代表的结构。还提供了含有这些化合物的药物组合物，以及它们的使用方法；本发明的化合物具有诸如抗病毒、抗病毒感染、神经保护、抗代谢性疾病等药理活性。还提供了天然产物咖啡碱、咖啡碱A和咖啡碱C的化学全合成制备方法。本发明为这些化合物作为未来临床药物深入研究和发展奠定了基础。
• Scandium triflate-catalyzed intramolecular Friedel–Crafts acylation with Meldrum's acids: insight into the mechanism
  作者：Eric Fillion、Dan Fishlock

  DOI：10.1016/j.tet.2009.05.058

  日期：2009.8

  Friedel–Crafts acylation of arenes with Meldrum's acid derivatives catalyzed by Sc(OTf)3 was reported as a mild and general entry into functionalized 1-indanones. Mechanistic investigations were undertaken to determine the rate-determining step in the acylation sequence using Meldrum's acid, as well as to examine the role of the Lewis acid catalyst. Enolizable Meldrum's acid derivatives react via an acyl ketene

  Sc（OTf）3催化芳烃的分子内Friedel-Crafts酰化与Meldrum酸衍生物据报道，这是轻度和普遍进入功能化的1-茚满酮。进行了机械研究，以确定使用Meldrum酸在酰化序列中确定速率的步骤，并研究了路易斯酸催化剂的作用。可烯醇化的Meldrum的酸衍生物在热条件下通过酰基乙烯酮中间体反应，而季铵化的Meldrum的酸衍生物具有热稳定性，仅在路易斯酸催化剂存在下才可充当有效的Friedel-Crafts酰化剂。假定酰化反应通过路易斯酸活化的羰基的直接酰化反应进行。在Meldrum酸的Friedel-Crafts催化酰化反应中，三氟甲磺酸似乎是活性催化物种，其中Sc（OTf）3 可以作为一种非常温和方便的试剂进行递送。
• Fracture Site-Specific Deficits in Bone Size and Volumetric Density in Men with Spine or Hip Fractures
  作者：Ego Seeman、Yunbo Duan、Christopher Fong、Jan Edmonds

  DOI：10.1359/jbmr.2001.16.1.120

  日期：——

  To study the structural basis of bone fragility in men, we compared bone size and volumetric bone mineral density (vBMD) of the third lumbar vertebra and femoral neck in 95 men with spine fractures, 127 men with hip fractures, and 395 healthy controls using dual‐energy X‐ray absorptiometry (DXA). The results were expressed in absolute terms and age‐specific SD scores (mean ± SEM). In controls, vertebral body and femoral neck width increased across age, being 0.46 ± 0.11 SD and 0.91 ± 0.08 SD higher in elderly men than in young men, respectively (both, p < 0.001). Men with spine fractures had reduced vertebral body width (−0.45 ± 0.10 SD; p < 0.01) but not femoral neck width (−0.15 ± 0.10 SD, NS). Men with hip fractures had reduced femoral neck width (−0.45 ± 0.11 SD; p < 0.01) and vertebral body width (−0.25 ± 0.10 SD; p < 0.05). The deficits in bone volume (BV) exaggerated the deficits in bone mineral content (BMC) by 40% at the vertebrae in men with spine fractures and by 9% at the femoral neck in men with hip fractures. vBMD deficits were greater at the vertebrae in men with spine fractures than in men with hip fractures (−1.37 ± 0.08 SD vs.−0.70 ± 0.10 SD, respectively; p < 0.01) but were similar at the femoral neck (−0.93 ± 0.10 SD and −0.76 ± 0.11 SD, respectively, NS), despite the men with spine fracture being 10 years younger. Bone fragility leading to spine or hip fractures in men may be the result of fracture site‐specific deficits in bone size and vBMD that have their origins in growth, aging, or both.

  为了研究男性骨脆弱性的结构基础，我们使用双能X射线吸收法（DXA）比较了95名脊椎骨折男性、127名髋关节骨折男性和395名健康对照的第三个腰椎和股骨颈的骨大小及体积骨密度（vBMD）。结果以绝对值和年龄特异的标准差（SD）分数（均值 ± 标准误）表示。在对照组中，椎体和股骨颈的宽度随年龄增长而增加，老年男性的椎体宽度比年轻男性高出0.46 ± 0.11 SD，股骨颈宽度高出0.91 ± 0.08 SD（均，p < 0.001）。脊椎骨折的男性椎体宽度降低（−0.45 ± 0.10 SD；p < 0.01），但股骨颈宽度没有显著降低（−0.15 ± 0.10 SD，NS）。髋关节骨折的男性股骨颈宽度（−0.45 ± 0.11 SD；p < 0.01）和椎体宽度（−0.25 ± 0.10 SD；p < 0.05）均有减少。骨体积（BV）的亏损在脊椎骨折男性的椎体区域使骨矿物质含量（BMC）的亏损加重了40%，在髋关节骨折男性的股骨颈区域则加重了9%。脊椎骨折男性的vBMD亏损在椎体区域大于髋关节骨折男性（分别为−1.37 ± 0.08 SD与−0.70 ± 0.10 SD；p < 0.01），但在股骨颈区域相似（分别为−0.93 ± 0.10 SD和−0.76 ± 0.11 SD，NS），尽管脊椎骨折的男性年龄比髋关节骨折的男性小10岁。导致男性脊椎或髋关节骨折的骨脆弱性可能源于特定骨折部位的骨大小和vBMD的亏损，这些亏损来源于生长、衰老或两者的结合。
• Staudinger; Hirzel, Chemische Berichte, 1916, vol. 49, p. 2526
  作者：Staudinger、Hirzel

  DOI：——

  日期：——
• Staudinger, Chemische Berichte, 1917, vol. 50, p. 1040
  作者：Staudinger

  DOI：——

  日期：——