ethyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate | 67077-19-4

• 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: ethyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate
• 英文别名: (2-oxo-4-phenyl-azetidin-1-yl)-acetic acid ethyl ester；ethyl 2-(2-oxo-4-phenylazetidin-1-yl)acetate
• CAS: 67077-19-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: IFMPRAYXLIVLDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以68%的产率得到(RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetic acid
  参考文献：
  名称：

  Studies on ketene and its derivatives. CXII. Reaction of ketene with Schiff bases to give .ALPHA.-unsubstituted .BETA.-lactams.

  摘要：

  研究了乙烯酮与席夫碱的反应。将乙烯酮与席夫碱（1a-l）在无溶剂条件下加热，得到了α-未取代的β-内酰胺（2a-l）。在不同温度下进行了乙烯酮与乙基N-糠叉甘氨酸盐（1k）反应生成β-内酰胺2k的研究，发现2k的产率受反应温度的影响不大。β-内酰胺（2d, f, k, l）在二恶烷中用10%氢氧化钠水溶液处理，以良好产率得到了相应的羧酸（4d, f, k, l）。化合物4d, f, l在二环己基碳二亚胺（DCC）存在下与各种胺反应，得到了相应的酰胺（5a-c, 8a-d）。

  DOI：

  10.1248/cpb.31.538
• 作为产物：
  描述：

  4-苯基-2-氮杂环丁酮 以78%的产率得到
  参考文献：
  名称：

  REUSCHLING D.; PIETSCH H.; LINKIES A., TETRAHEDRON LETT. , 1978, NO 7, 615-618

  摘要：

  DOI：

文献信息

• β-Lactam Derivatives as Enzyme Inhibitors: 1-Peptidyl Derivatives of 4-Phenylazetidin-2-one as Inhibitors of Elastase and Papain
  作者：Karin Achilles、Tanja Schirmeister、Hans-Hartwig Otto

  DOI：10.1002/1521-4184(20008)333:8<243::aid-ardp243>3.0.co;2-o

  日期：2000.8

  hydrolysis to the free acid, was acylated with amino acid esters or di‐ or tripeptide esters. The enzymatic assays proved some derivatives to be effective inhibitors of PPE and/or papain. N‐BOC protected amino acid derivatives without a spacer group inhibited PPE reversibly, while derivatives with spacer group showed either weak or no inhibitory properties. On the other hand, papain was inactivated irreversibly

  N-Peptidyl 取代的 azetidin-2-ones 被合成并评估为丝氨酸蛋白酶弹性蛋白酶和半胱氨酸蛋白酶木瓜蛋白酶的抑制剂。所有化合物均由 4-苯基氮杂环丁烷-2-one 合成，无论是外消旋体还是纯对映体。(S)-对映异构体由(S)-β-苯基-β-丙氨酸通过对映选择性合成制备，而(R)-对映异构体通过用α-胰凝乳蛋白酶进行酶促拆分获得。用溴乙酸酯进行 N-烷基化引入了一个间隔基团，在水解成游离酸后，该基团被氨基酸酯或二肽或三肽酯酰化。酶促测定证明一些衍生物是 PPE 和/或木瓜蛋白酶的有效抑制剂。没有间隔基团的 N-BOC 保护的氨基酸衍生物可逆地抑制 PPE，而带有间隔基团的衍生物表现出弱或没有抑制特性。另一方面，木瓜蛋白酶被 (RS)-2-oxo-4-phenylazetidin-1-乙酸乙酯不可逆地灭活。N-(2-oxo-4-phenylazetidin-1-acetyl)
• β-Lactam Derivatives as Enzyme Inhibitors: Peptidic Derivatives of (RS)-2-Oxo-4-phenylazetidine-1-alkanoic Acids
  作者：Ali Elriati、Karin Achilles、Jutta Loose、Hans-Hartwig Otto

  DOI：10.1007/s00706-007-0639-9

  日期：2007.6

  4-Phenylazetidine-2-one was transformed into 4-phenylazetidine-1-alkanoic acids, which were reacted in the presence of diphenylphosphoroazidate with amino acid esters and dipeptide esters yielding beta-lactam peptides with different spacers between the lactam ring and the peptide moiety. All structures were established by elementary analyses, HPLC, optical rotation, and spectroscopic data and all new compounds were tested as inhibitors of PPE using standard procedures. Four compounds exhibited a weak activity compared with the standard inhibitor trifluoroacetyl-L-val-L-tyr-L-val.
• Studies on ketene and its derivatives. CXII. Reaction of ketene with Schiff bases to give .ALPHA.-unsubstituted .BETA.-lactams.
  作者：NOBUYA KATAGIRI、YUTAKA MIURA、RYUJI NIWA、TETSUZO KATO

  DOI：10.1248/cpb.31.538

  日期：——

  The reaction of ketene with Schiff bases was investigated. Heating of ketene with Schiff bases (1a-l) without solvent gave α-unsubstituted β-lactams (2a-l). The reaction of ketene with ethyl N-furfurylideneglycinate (1k) to give the β-lactam 2k was carried out at various temperatures, and it was found that the yield of 2k was not much influenced by the reaction temperature. β-Lactams (2d, f, k, l) were treated with 10% aqueous sodium hydroxide in dioxane to give the corresponding carboxylic acids (4d, f, k, l) in good yields. Compounds 4d, f, l reacted with various amines in the presence of dicyclohexylcarbodiimide (DCC) to give the corresponding amides (5a-c, 8a-d).

  研究了乙烯酮与席夫碱的反应。将乙烯酮与席夫碱（1a-l）在无溶剂条件下加热，得到了α-未取代的β-内酰胺（2a-l）。在不同温度下进行了乙烯酮与乙基N-糠叉甘氨酸盐（1k）反应生成β-内酰胺2k的研究，发现2k的产率受反应温度的影响不大。β-内酰胺（2d, f, k, l）在二恶烷中用10%氢氧化钠水溶液处理，以良好产率得到了相应的羧酸（4d, f, k, l）。化合物4d, f, l在二环己基碳二亚胺（DCC）存在下与各种胺反应，得到了相应的酰胺（5a-c, 8a-d）。
• REUSCHLING D.; PIETSCH H.; LINKIES A., TETRAHEDRON LETT. <TELE-AY>, 1978, NO 7, 615-618
  作者：REUSCHLING D.、 PIETSCH H.、 LINKIES A.

  DOI：——

  日期：——