(3R,4S)-3-(buta-1,3-dien-1-yl)-1,4-diphenylazetidin-2-one | 1092576-82-3

• 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: (3R,4S)-3-(buta-1,3-dien-1-yl)-1,4-diphenylazetidin-2-one
• CAS: 1092576-82-3
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: XGAPZWPGTLPPDP-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-(buta-1,3-dien-1-yl)-1,4-diphenylazetidin-2-one 在 盐酸羟胺 、 sodium acetate 、 四氯化锡 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.2h， 生成 2-oxy-4(RS)-[4-(SR)(phenyl-phenylamino-methyl)]-4a(SR),7,8,8a(SR)-tetrahydro-4H-isoquinolin-3-one
  参考文献：
  名称：

  Single pot diastereoselective synthesis of six membered cyclic (E)-endo-aldonitrones via intramolecular cyclization of ω-alkenyl oximes

  摘要：

  beta-Lactam-synthon interceded diastereoselective single pot synthesis of synthetically challenging six-membered cyclic (E)-endo-aldonitrones has been developed via intramolecular cyclization of omega-alkenyl oximes tethered at the C-3 position of 2-azetidinones along with its utilization in 1,3-dipolar cycloaddition reaction with DMAD. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.023
• 作为产物：
  描述：

  N-苄叉苯胺 、 山梨酸氯化物 在 三乙胺 作用下， 生成 (3R,4S)-3-(buta-1,3-dien-1-yl)-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines via NaBH4-promoted facile reduction of C-3 functionalized azetidin-2-ones

  摘要：

  A facile diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines has been reported via NaBH4-promoted reduction of C-3 functionalized azetidin-2-ones. Since the developed protocol does not involve the use of a Lewis acid, the methodology does not suffer from typical drawbacks of the conventional protocol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.126

文献信息

• Regio- and Chemoselective Unprecedented Imino-Diels-Alder Reactions of 1-Substituted Unactivated Dienes with <i>N</i>-Aryl Imines - Part II
  作者：Mohinder Mahajan、Gaurav Bhargava、Takao Saito

  DOI：10.1055/s-2008-1072507

  日期：——

  The chemo- as well as regioselective participation of N-aryl imines as 4π component in aza-Diels-Alder reactions with 3-butadienyl-2-azetidinones in the presence of Lewis acid catalysts resulting in novel quinoline derivatives is described.

  该文描述了N-芳基亚胺作为4π组分在Lewis酸催化剂存在下，与3-丁二烯基-2-氮杂环丁酮参与的氮杂Diels-Alder反应中的化学选择性和区域选择性，从而产生新颖的喹啉衍生物。
• Regio- and Diastereoselective Nitroso Diels-Alder Cycloaddition Reactions of 3-dienyl-2-azetidinones with Nitrosoarenes
  作者：Amit Anand、Gaurav Bhargava、Pardeep Singh、Saloni Mehra、Vipan Kumar、Mohinder P. Mahajan、Parvesh Singh、Krishna Bisetty

  DOI：10.2174/157017812801322444

  日期：2012.6.1

  The regioselective nitroso Diels-Alder (NDA) reactions of trans 3-butadienyl-2-azetidinones with nitrosoarenes leading to the synthesis of novel and diastereomerically pure 3-(3,6-dihydro-2H-1, 2-oxazin-6-yl) azetidin-2-one derivatives and cis 3-butadienyl-2-azetidinones resulting in a diastereoselective mixture of regioisomers are investigated. The observed regioselective behavior is supported by computational model, Ab initio [HF/6-31G (d)] and density functional theory [B3LYP/6-31G (d)] calculations. Additionally, the effect of solvation (in dichloromethane) in these reactions was also investigated in order to mimic the experimental solvent conditions.

  研究了反式 3-丁二烯基-2-氮杂环丁酮与亚硝基烯烃的区域选择性亚硝基 Diels-Alder (NDA)反应，从而合成了新型非对映纯的 3-(3,6-二氢-2H-1,2-恶嗪-6-基) 氮杂环丁烷-2-酮衍生物和顺式 3-丁二烯基-2-氮杂环丁酮，并产生了非对映选择性的区域异构体混合物。观察到的区域选择性行为得到了计算模型、Ab initio [HF/6-31G (d)] 和密度泛函理论 [B3LYP/6-31G (d)] 计算的支持。此外，为了模拟实验溶剂条件，还研究了溶解（在二氯甲烷中）对这些反应的影响。
• Facile, diastereoselective synthesis of functionally enriched hexahydroisoquinolines, hexahydroisoquinolones and hexahydroisochromones via inter-/intramolecular amidolysis of C-3 functionalized 2-azetidinones
  作者：Vishu Mehra、Vipan Kumar

  DOI：10.1016/j.tet.2013.03.044

  日期：2013.5

  We describe herein the synthetic utility of β-lactam synthon protocol for the convenient and diastereoselective synthesis of functionally decorated hexahydroisoquinolines, hexahydroisoquinolones and hexahydroisochromones. Since the described protocol does not include the use of highly functionalized intermediates, stringent conditions or toxic reagents, the developed methodology does not suffer from

  我们在本文中描述了β-内酰胺合成子方案的合成效用，用于功能修饰的六氢异喹啉，六氢异喹啉酮和六氢异色酮的方便和非对映选择性合成。由于所描述的方案不包括使用高度官能化的中间体，严格条件或有毒试剂，因此开发的方法不会遭受与常规方案相关的典型复杂性的困扰。
• Facially Selective Oxo-Diels-Alder Cycloadditions of α-Dienyl-β-Lactam: An Entry to Pyrano Tethered β-Lactams Bifunctional Hybrids
  作者：Maninderjeet Kaur Mann、Rupesh Kumar、Gaurav Bhargava

  DOI：10.13005/ojc/380334

  日期：2022.6.30

  The functionalization of -lactams at C-3 position are useful for the strategic improvement in both the dimensions, namely synthetic utility, as versatile intermediate in organic synthesis and biological potential of these heterocyclic systems. The present manuscript involved the -facial selective synthesis -lactam hybrids employing highly regioselective and diastereoselective oxo-Diels–Alder reactions of diethyl ketomalonate with -dienyl--lactam with stereocentres at its - and - positions. This protocol provided the cycloaddition of - and - stereocentric diene with symmetrical heterodienophiles forming biologically potent regioselective and diastereoselective -lactams substituted pyrano bifunctional hybrids in good yields and -facially selectivity.

   内酰胺在 C-3 位的官能化有助于从两个方面进行战略改进，即作为有机合成的多功能中间体的合成效用和这些杂环系统的生物潜力。本手稿涉及 -面选择性合成 -内酰胺混合物，采用的是酮丙二酸二乙酯与 -二烯基--内酰胺的高区域选择性和非对映选择性氧化-Diels-Alder 反应，该反应的立体中心位于 - 和 -位。该方案提供了 - 和 - 立体中心二烯与对称杂二烯类的环加成反应，以良好的产率和 - 面选择性形成了具有生物活性的区域选择性和非对映选择性的 - 内酰胺取代吡喃双官能团杂交化合物。
• PASS-assisted exploration of antidepressant activity of 1,3,4-trisubstituted-β-lactam derivatives
  作者：Munish Mittal、Rajesh K Goel、Gaurav Bhargava、Mohinder P Mahajan

  DOI：10.1016/j.bmcl.2008.09.064

  日期：2008.10

  Assisted by PASS predictions, the antidepressant activity of 1,3,4-trisubstituted monocyclic beta-lactams in seasonal affective disorders is described. (C) 2008 Elsevier Ltd. All rights reserved.