benzyl 3-oxo-5-phenylpentanoate | 62282-45-5

• 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: benzyl 3-oxo-5-phenylpentanoate
• CAS: 62282-45-5
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: QGGPYMCNUASRGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  benzyl 3-oxo-5-phenylpentanoate 在 palladium on activated charcoal sodium hydroxide 、 三氯化铝 、 草酰氯 、 氢气 、 sodium acetate 、 potassium carbonate 、 锌 、 sodium nitrite 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 18.0h， 生成 3-carboxy-1,4,5,10-tetrahydro-1-methyl-10-oxobenzo<5,6>cyclohepta<1,2-b>pyrrole-2-acetic acid
  参考文献：
  名称：

  4,5,8,9-四氢-8-甲基-9-氧噻吩并[3'，2'：5,6]环庚[1,2 - b ]-吡咯-7-乙酸。新型消炎/镇痛药

  摘要：

  据报道由吗啉3合成噻吩并环庚[1，2- b ]吡咯酸1。该新型吗啉化物是通过4-（1，3-二氧杂丁基）吗啉与3-溴甲基噻吩的二价阴离子的区域特异性烷基化制备的。随后的克诺尔吡咯合成导致吗啉化物8b，其在维尔斯迈尔条件下转化为所需的三环系统。使用涉及Friedel-Crafts环化的替代方法来制备相关的苯并环庚吡咯2。

  DOI：

  10.1002/jhet.5570200437
• 作为产物：
  描述：

  3-氧代-5-苯基-戊酸乙酯 在 苯甲醇 作用下， 生成 benzyl 3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  10 Oxo-4,5-dihydro-10H-benzo 5,6 cycloheph[1,2-B]pyrryls

  摘要：

  公式（II）的化合物：##STR1##其中R是C.sub.1-4烷基基团；R.sub.1是氢原子或C.sub.1-4烷基基团；R.sub.2是氢原子或卤素原子，或C.sub.1-4烷基、C.sub.1-4烷氧基或C.sub.1-4烷硫基团；以及它们的前体药物；以及公式（II）化合物及其前体药物的药用盐；具有有用的抗炎和镇痛活性。

  公开号：

  US04444981A1

文献信息

• Nuclear analogs of β-lactam antibiotics. II. Synthesis of <i>O</i>-2-isocephems
  作者：Terrence W. Doyle、Bernard Belleau、Bing-Yu Luh、Terry Thomas Conway、Marcel Menard、James L. Douglas、Daniel Tim-Wu Chu、Gary Lim、Leeson R. Morris、Pierre Rivest、Michael Casey

  DOI：10.1139/v77-070

  日期：1977.2.1

  The preparation by total synthesis of a new class of β-lactam antibiotics is reported. Conversion of alcohol 1b to its mesylate 9b followed by hydrolysis of the acetal to the enol 1b and base-catalyzed ring closure gave benzyl 7- β-azido-Δ³-O-2-isocephem-4-carboxylate 8b. Similarly prepared were the 3 -methyl, 3 -benzyl, and 3 -phenethyl analogs (32b–d). Reduction of the azides followed by coupling of the resultant amines with phenoxyacetic acid and removal of the benzyl groups by hydrogenolysis gave the acids 35a–e which exhibited high antibacterial activity. The structural assignments to the O-2-isocephems which were made on the basis of their spectral characteristics (ir, uv, and nmr) are discussed.

  报道了一种新类β-内酰胺类抗生素的全合成制备。将醇1b转化为其甲磺酸酯9b，随后水解缩醛为烯醇1b，并经过碱催化的环闭合得到苄基7-β-叠氮-Δ3-O-2-异头孢-4-羧酸酯8b。类似地制备了3-甲基、3-苄基和3-苯乙基类似物（32b–d）。还原叠氮基后，将产生的胺与苯氧乙酸偶联，并通过氢解去除苄基，得到表现出高抗菌活性的酸35a–e。基于它们的光谱特性（红外光谱、紫外光谱和核磁共振）对O-2-异头孢的结构分配进行了讨论。
• 10H-1-Alkyl-10-oxabenzo,5,6 cyclohepta[1,2-G]pyrrole-2-acetic acids
  申请人：Beecham Group Limited

  公开号：US04359423A1

  公开（公告）日：1982-11-16

  A compound of formula (II): ##STR1## wherein R is a C.sub.1-4 alkyl group; R.sub.1 is a hydrogen atom or a C.sub.1-4 alkyl group; R.sub.2 is a hydrogen or halogen atom, or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkylthio group; and pro-drugs thereof; and the pharmaceutically acceptable salts of the compounds of formula (II) and of their pro-drugs; has useful anti-inflammatory and analgesic activity.

  式（II）的化合物：##STR1##其中R是C.sub.1-4烷基；R.sub.1是氢原子或C.sub.1-4烷基；R.sub.2是氢或卤素原子，或C.sub.1-4烷基，C.sub.1-4烷氧基或C.sub.1-4烷硫基；以及它们的前药和化合物的药物可接受的盐（II）的，具有有用的抗炎和镇痛活性。
• Continuous‐Flow Synthesis of β‐Ketoesters and Successive Reactions in One‐Flow using Heterogeneous Catalysis
  作者：Mohanraj Kandasamy、Haruro Ishitani、Shū Kobayashi(s)

  DOI：10.1002/adsc.202200602

  日期：2022.10.4

  A continuous-flow procedure for the synthesis of β-ketoesters has been developed through Roskamp reaction between aldehydes and diazoesters in the presence of a Sn-MCM-41 catalyst. The viability of this methodology was confirmed with a range of aromatic and aliphatic aldehydes with diazoesters and provided good to excellent yields. Catalyst activity was tested over three days (84 hours) of operation

  在 Sn-MCM-41 催化剂存在下，通过醛和重氮酯之间的 Roskamp 反应，开发了一种用于合成 β-酮酯的连续流动程序。该方法的可行性得到了一系列芳香族和脂肪族醛与重氮酯的确认，并提供了良好的收率。在三天（84 小时）的操作中测试了催化剂活性，所需 β-酮酯的产率保持在 73% 至 89% 之间。所制备的β-酮酯通过连续缩合反应顺利转化为香豆素衍生物和5-吡唑啉酮。
• Oxone-promoted hydration of electron-deficient allenic esters and ketones into 1,3-dicarbonyl compounds
  作者：Yu-Ping Yi、Yan Zheng、Jing Nie、Jun-An Ma

  DOI：10.1016/j.tetlet.2015.05.120

  日期：2015.7

  A novel and mild protocol for the hydration of electron-deficient allenic esters and ketones into various 1,3-dicarbonyl compounds is described. The hydration of allenes promoted by oxone in DMF afforded the corresponding products in moderate to good yields. This work features the employment of only a catalytic amount of inexpensive and nontoxic solid reagent oxone (2KHSO(5)center dot KHSO4 center dot K2SO4), avoiding the utility of toxic metals or traditional Bronsted acids, in a green version of viewpoint. A possible reaction mechanism for this transformation is also primarily proposed. (C) 2015 Elsevier Ltd. All rights reserved.
• GOUDIE, A. C.;WARD, R. W.
  作者：GOUDIE, A. C.、WARD, R. W.

  DOI：——

  日期：——