trans-1,4-diphenyl-3-vinyl-2-azetidinone | 33812-87-2

• 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: trans-1,4-diphenyl-3-vinyl-2-azetidinone
• 英文别名: trans-1,4-diphenyl-3-vinylazetidin-2-one；(3R,4S)-3-ethenyl-1,4-diphenylazetidin-2-one
• CAS: 33812-87-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: QWTZRYZXDPDJOD-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-1,4-diphenyl-3-vinyl-2-azetidinone 在 copper(l) chloride 、 palladium dichloride sodium tetrahydroborate 、 氯化亚砜 、 氧气 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2-chloroethyl)-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  3-乙烯基-4-取代的2-氮杂环丁烷酮的新型化学转化

  摘要：

  描述了涉及抗马尔科夫尼科夫加成反应的α-乙烯基-β-内酰胺的转化。的PdCl的动作2 CuClO 2上的乙烯基通向终端醛而不是预期的甲基酮。通过还原该醛基，然后将伯羟基转化为氯衍生物而制得的中间体以高收率重排为1，2-二芳基-3-羰基甲氧基吡咯烷。

  DOI：

  10.1016/s0040-4039(00)85371-x
• 作为产物：
  描述：

  丁-3-烯酰氯 、 N-苄叉苯胺 在 N-甲基吗啉 作用下， 生成 trans-1,4-diphenyl-3-vinyl-2-azetidinone
  参考文献：
  名称：

  Microwave-Assisted Rapid and Simplified Hydrogenation^1,

  摘要：

  Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 degrees C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 degrees C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of beta-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters, Cleavage of the beta-lactam ring by hydrogenolysis of the N-C-4 bond of 4-aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

  DOI：

  10.1021/jo981516s

文献信息

• The Stereoselective Synthesis of Alkenyl-β-lactams by Palladium-Catalyzed [2+2] Carbonylative Cycloaddition
  作者：Luigino Troisi、Luisella De Vitis、Catia Granito、Erbana Epifani

  DOI：10.1002/ejoc.200300667

  日期：2004.3

  Allyl halides of different structures, under CO pressure, in the presence of Et3N, a catalytic amount of Pd(OAc)2, and triphenylphosphane as ligand, undergo a [2+2] cycloaddition reaction with various imines. The reaction is highly regio- and stereoselective: β-lactams are formed in good yields and with trans diastereoselectivity in both the β-lactam ring and the vinylic moiety. New and important information

  不同结构的烯丙基卤在 CO 压力下，在 Et3N、催化量的 Pd(OAc)2 和作为配体的三苯基膦存在下，与各种亚胺发生 [2+2] 环加成反应。该反应具有高度的区域选择性和立体选择性：β-内酰胺以良好的产率形成，并且在 β-内酰胺环和乙烯基部分均具有反式非对映选择性。建议了关于已知反应机理的新的和重要的信息。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Tandem-Selective Bond Cleavage of the Lactam Nucleus and Michael Reaction
  作者：Luisella De Vitis、Luigino Troisi、Catia Granito、Emanuela Pindinelli、Ludovico Ronzini

  DOI：10.1002/ejoc.200600597

  日期：2007.1

  The reactivity of the β-lactam ring towards nucleophiles has been investigated. Ring-opening reactions were performed on 3-allyl-β-lactams with CH3O–/CH3OH at room temperature and/or reflux. Lactam nucleus isomerization followed by N1–C2 bond cleavage and methanol Michael addition afforded substituted amino esters. The reactivity of the four-membered ring towards nucleophiles was found to depend on

  已经研究了 β-内酰胺环对亲核试剂的反应性。在室温和/或回流下，用 CH3O-/CH3OH 对 3-烯丙基-β-内酰胺进行开环反应。内酰胺核异构化，然后 N1-C2 键断裂和甲醇迈克尔加成得到取代的氨基酯。发现四元环对亲核试剂的反应性取决于内酰胺氮以及 C3 和 C4 原子上的取代基。本报告突出显示了开环路径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Triflic acid promoted fries rearrangement of C-3 vinyl/isopropenyl-azetidin-2-ones: single-pot synthesis of C-3 functionalized-2-aryl-2,3-dihydro-quinoline-4(1H)-ones
  作者：Vishu Mehra、Parvesh Singh、Krishna Bisetty、Vipan Kumar

  DOI：10.1039/c4ra07452a

  日期：——

  The β-lactam-synthon-interceded synthesis of C-3 functionalized 2-aryl-2,3-dihydro-quinoline-4(1H)-ones has been described via the Fries rearrangement of C-3 vinyl/isopropenyl substituted β-lactams. The reaction at 0 °C resulted in the isolation of a tautomeric mixture, and the preferential formation of the conjugated product was observed at higher temperatures. Density functional theory (DFT) calculations

  通过C-3乙烯基/异丙烯基取代的β-的弗里斯重排描述了C-3官能化的2-芳基-2,3-二氢喹啉-4（1 H）-ones的β-内酰胺基间位合成内酰胺。在0℃下的反应导致互变异构混合物的分离，并且在更高的温度下观察到了优先形成的共轭产物。此外，还进行了密度泛函理论（DFT）计算和分子动力学（MD）模拟，以解释2相对于3的优先形成。通过碱诱导的2a和3a混合物的异构化，进一步验证了所提出的机理。
• 4-Acetoxy-3-[1-(2-arylamino-1-hydroxy)ethyl]azetidin-2-one s: Intermediates for the Synthesis of Novel Carbapenems
  作者：Mary J. Meegan、Caroline M. Waldron、Raymond D. Keaveny、Anthony D. Neary

  DOI：10.1039/a700513j

  日期：——

  3-Vinyl- and 3-isopropenyl-azetidin-2-ones are transformed into the corresponding 4-acetoxy-3-[1-(2-arylamino-1-hydroxy)ethyl]azetidin-2-ones and 4-acetoxy-3-[1-(2-arylamino-1-hydroxy)propyl]azetidin-2-ones, intermediates for the synthesis of novel carbapenems.

  将 3-乙烯基和 3-异丙烯基氮杂环丁烷-2-酮转化为相应的 4-乙酰氧基-3-[1-(2-芳基氨基-1-羟基)乙基]氮杂环丁烷-2-酮和 4-乙酰氧基-3-[1-(2-芳基氨基-1-羟基)丙基]氮杂环丁烷-2-酮，这是合成新型碳青霉烯类化合物的中间体。
• The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp2TiCl2 (cat.)
  作者：Lei Chen、Gang Zhao、Yu Ding

  DOI：10.1016/s0040-4039(03)00187-4

  日期：2003.3

  In the presence of Zn/Cp2TiCl2 (cat.) alpha-bromoacetates, gamma-bromocrotonates or alpha-bromomethylacrylates react with imines in one-pot to form beta-lactams, 3-vinyl-beta-lactams or alpha-methylene-gamma-lactams, respectively, at room temperature without the need for pretreatment of the solvent and Zn. (C) 2003 Elsevier Science Ltd. All rights reserved.