4-(Benzoylmethyl)azetidin-2-one | 76127-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-(Benzoylmethyl)azetidin-2-one
• 英文别名: 4-phenylcarbonylmethyl-2-azetidinone；4-Phenacyl-azetidin-2-one；4-phenacylazetidin-2-one
• CAS: 76127-62-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: NKVFCWFKCHZKSH-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  411.9±18.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(Benzoylmethyl)azetidin-2-one 在 2,6-二甲基吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 Chloro-[2-oxo-4-(2-oxo-2-phenyl-ethyl)-azetidin-1-yl]-acetic acid benzyl ester
  参考文献：
  名称：

  Synthetic approach directed at 1-carbapenems and 1-carbapenams.

  摘要：

  4-乙酰氧基-2-氮杂环丁酮（2）中乙酰氧基团与铝烯醇盐的置换反应生成了4-烷基氮杂环丁酮4a、5a、10和11。对这些氮杂环丁酮转化为1-碳氟烯酮或-烯酮化合物进行了研究。

  DOI：

  10.1248/cpb.28.3494
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 4-acetoxy-1-trimethylsilylazetidin-2-one 在 potassium fluoride 、 三氟甲磺酸三甲基硅酯 作用下， 生成 4-(Benzoylmethyl)azetidin-2-one
  参考文献：
  名称：

  简明合成4-（芳基羰基甲基）-氮杂环丁烷-2-酮及相关体系

  摘要：

  在三甲基甲硅烷基三氟甲烷磺酸酯的催化下，4-乙酰氧基-1-三甲基甲硅烷基氮杂环丁烷-2-one与烯醇硅烷[R 1 CH C（OSiMe 3）R 2 ]反应，得到β-内酰胺[[略图] HCH（R）1）COR 2 ]，收率极高（71％至95％）。

  DOI：

  10.1039/c39810001076

文献信息

• Synthetic approaches to thienamycin: Carbon-carbon bond formation at C-4 of azetidin-2-ones
  作者：Paul J. Reider、Richard Rayford、Edward J.J. Grabowski

  DOI：10.1016/s0040-4039(00)86836-7

  日期：——

  A mild and efficient method of β-lactam alkylation has been achieved using 4-acetoxy-2-azetidinone and a variety of silyl enol ethers.

  使用4-乙酰氧基-2-氮杂环丁酮和各种甲硅烷基烯醇醚已实现了温和有效的β-内酰胺烷基化方法。
• Studies on 1-carbadethiacephems, part II: Reaction of 4-acetoxy-2-azetidinone with aluminium enolates
  作者：C.W. Greengrass、M.S. Nobbs

  DOI：10.1016/s0040-4039(01)92496-7

  日期：——

  A procedure for the novel reaction of αβ-unsaturated ketones (as zinc-free aluminium enolates) with 4-acetoxy-2-azetidinone, giving products , is reported. A 1-carbadethia-2-oxocephem derivative has been prepared from compound .

  报道了一种α-不饱和酮（无锌烯醇铝）与4-乙酰氧基-2-氮杂环丁酮新反应的方法，得到了产物。由化合物制备了1-卡巴地亚-2-氧代头孢烯衍生物。
• SmI₂-Mediated Cyclizations of Derivatized β-Lactams for the Highly Diastereoselective Construction of Functionalized Prolines
  作者：Mikkel F. Jacobsen、Maris Turks、Rita Hazell、Troels Skrydstrup

  DOI：10.1021/jo0104983

  日期：2002.4.1

  A series of C4-keto-functionalized 1-[(benzoyloxy)(ethoxycarbonyl)methyl]-2-azetidinones were prepared and studied for their tendency to undergo a Reformatsky-type cyclization to fused bicyclic or tricyclic beta-lactams with the single-electron reducing agent samarium diiodide. Whereas the azetidinone 21a underwent reductive cyclization, affording the potent antibiotic sanfetrinem's tricyclic [4.5.6] core structure as the major component, all other examples tested resulted in cyclization followed by an N to O acyl migration involving cleavage of the beta-lactam ring as the favored pathway. Highly functionalized proline derivatives were therefore accessed as single diastereomers through the reductive cyclization of benzoates 21b, 22, 23a,b, 24b, and 25-28. Pertinent for the success of these cyclizations was the addition of 1 equiv of tert-butyl alcohol, allowing for the protonation of the basic amide derivative obtained after the acyl migration step. The diastereoselectivities of these reactions deviate from those of similar cyclizations involving the corresponding lithium enolate. This divergence could be rationalized by the coordination of the metal ion of the samarium(III) enolate intermediate to the beta-lactam amide functionality in the cyclization step, which may not be possible for lithium enolates.
• Convenient synthesis of .alpha.-(2-oxoazetidin-4-yl) esters and ketones and related systems
  作者：Robin P. Attrill、Anthony G. M. Barrett、Peter Quayle、Jan Van der Westhuizen、Michael J. Betts

  DOI：10.1021/jo00184a001

  日期：1984.5
• BARRETT, A. G. M.;QUAYLE, P., J. CHEM. SOC. CHEM. COMMUN., 1981, N 20, 1076-1077
  作者：BARRETT, A. G. M.、QUAYLE, P.

  DOI：——

  日期：——