trans-3-(1,3-butadienyl)-1-phenyl-(4-methoxyphenyl)azetidin-2-one

• 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-3-(1,3-butadienyl)-1-phenyl-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3R,4S)-3-[(1E)-buta-1,3-dienyl]-4-(4-methoxyphenyl)-1-phenylazetidin-2-one
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: FYOCJRZBKCNMSW-AAPPYSIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 trans-3-(1,3-butadienyl)-1-phenyl-(4-methoxyphenyl)azetidin-2-one 以 二氯甲烷 为溶剂， 反应 0.17h， 以92%的产率得到5-[(2R,3R)-2-(4-methoxyphenyl)-4-oxo-1-phenylazetidin-3-yl]-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
  参考文献：
  名称：

  A Convenient Trans Diastereoselective Synthesis of 3-Butadienylazetidinones and Their Diels−Alder Cycloaddition Reactions

  摘要：

  An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.

  DOI：

  10.1021/jo952249i
• 作为产物：
  描述：

  山梨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 生成 trans-3-(1,3-butadienyl)-1-phenyl-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  A Convenient Trans Diastereoselective Synthesis of 3-Butadienylazetidinones and Their Diels−Alder Cycloaddition Reactions

  摘要：

  An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.

  DOI：

  10.1021/jo952249i

文献信息

• Highly Diasteroselective and Remarkably π-Facially Selective Lewis Acid-Catalysed Diels-Alder Cycloaddition Reactions: Access to Novel 1,3,4-Trisubstituted 2-Azetidinones
  作者：Gaurav Bhargava、Mohinder P. Mahajan、Takao Saito、Takashi Otani、Mai Kurashima、Ken Sakai

  DOI：10.1002/ejoc.200500013

  日期：2005.6

  intermolecular Diels–Alder reactions of 3-butadienylazetidin-2-ones with a variety of symmetrical dienophiles (maleic anhydride, N-phenylmaleimide, N-p-tolylmaleimide, benzoquinone and naphthoquinone) resulting in the synthesis of diastereomerically pure 1,3,4-trisubstituted 2-azetidinones are reported. The effects of different Lewis acids on the yields of the selectively formed diastereoisomers under different

  3-丁二烯基氮杂环丁烷-2-酮与各种对称亲二烯体（马来酸酐、N-苯基马来酰亚胺、Np-甲苯基马来酰亚胺、苯醌和萘醌）的非对映选择性和π-面选择性路易斯酸催化的分子间Diels-Alder反应合成报道了非对映异构纯的 1,3,4-三取代 2-氮杂环丁酮。还研究了不同路易斯酸对不同反应条件下选择性形成的非对映异构体产率的影响。不同亲二烯体的路易斯酸配合物与二烯基氮杂环丁烷-2-酮中的羰基氧之间的优先螯合已被用来解释观察到的 π 面选择性。亲二烯体的路易斯酸配合物已被证明优先从二烯的 si 面接近，导致形成 π 面选择性“内”加合物。这些“内”加合物的结构甚至得到了 X 射线衍射研究的支持。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Regio- and π-facial selective Lewis acid interceded Diels–Alder reactions of α-dienyl-β-lactams: an indepth analysis
  作者：Gaurav Bhargava、Amit Anand、Mohinder P. Mahajan、Takao Saito、Ken Sakai、Chitrani Medhi

  DOI：10.1016/j.tet.2008.04.087

  日期：2008.7

  The regio-, diastereo-, and π-facial selective Lewis acid mediated Diels–Alder reactions of cis/trans-3-butadienyl-2-azetidinones with unsymmetrical dienophiles viz. methyl acrylate, dimethyl fumarate, and acrolein leading to the synthesis of diastereomerically pure and biologically potent 1,3,4-trisubstituted-2-azetidinones are reported. Theoretical calculations at HF/6-31G∗∗ and 6-31G∗∗/DFT levels

  区域，非对映体和π界面选择性路易斯酸介导的顺/反-3-丁二烯基-2-氮杂环丁酮与不对称亲双烯体的Diels-Alder反应，即。据报道，丙烯酸甲酯，富马酸二甲酯和丙烯醛可合成非对映体纯且生物学上有效的1,3,4-三取代-2-氮杂环丁酮。为了支持观察到的π面选择性，已经进行了HF / 6-31G **和6-31G ** / DFT的理论计算。非对映体纯的“内”加合物的形成得到X射线衍射研究的支持。
• A Facile Sodium Alkoxide Mediated Ring Opening of Unactivated a-Dienyl-b-lactams: Synthesis of Unnatural Multicomponent b-Aminodienoic Esters
  作者：Mohinder P. Mahajan、Amit Anand、Gaurav Bhargava、Maninder Singh Hundal

  DOI：10.3987/com-07-s(u)48

  日期：——
• Goel; Thind; Bal, Pharmazie, 2005, vol. 60, # 5, p. 369 - 374
  作者：Goel、Thind、Bal、Mahajan、Kulkarni

  DOI：——

  日期：——
• Sharma, Arun K.; Kumar, R. Senthil; Mahajan, Mohinder P., Heterocycles, 2000, vol. 52, # 2, p. 603 - 619
  作者：Sharma, Arun K.、Kumar, R. Senthil、Mahajan, Mohinder P.

  DOI：——

  日期：——