ethyl (2S)-1-(diphenylphosphoryl)-2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate | 1023287-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: ethyl (2S)-1-(diphenylphosphoryl)-2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: ethyl (2S)-1-diphenylphosphoryl-2-phenyl-2,5-dihydropyrrole-3-carboxylate
• CAS: 1023287-79-7
• 化学式: C₂₅H₂₄NO₃P
• 分子量: 417.444
• InChiKey: TVPOOVRQHLTSKO-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-丁炔酸乙酯 、 N-亚苄基-P,P-二苯基次膦酸酰胺 在 4-t-butyl-4,5-dihydro-3H-dinaphtho[2,1-c;1',2'-e]phosphepine 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以20%的产率得到ethyl (2S)-1-(diphenylphosphoryl)-2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  N-Ts-和 N-DPP-亚胺与烯丙酸酯和 2-丁酸酯的对映选择性双萘膦促进 [3+2] 环化

  摘要：

  研究了双萘膦 1a 用作烯丙酸酯或 2-丁酸酯和亚胺之间 [3+2] 环化的催化剂。通过比较 N-甲苯磺酰基-和 N-DPP-亚胺的行为，确定亚胺保护基团对催化活性和对映选择性的影响。N-DPP-亚胺表现出较低的反应性，但以更高的对映体过量（73-92％ee）提供所需的吡咯啉。在温和条件下从最终的吡咯啉中除去 DPP 保护基团，得到相应的仲胺。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200800598

文献信息

• Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines
  作者：Xiaoyu Han、Fangrui Zhong、Youqing Wang、Yixin Lu

  DOI：10.1002/anie.201106672

  日期：2012.1.16

  A fast one: The title reaction proceeds in the presence of 5 mol % of the catalyst 1, and is complete within an hour. The 2‐alkyl‐ and 2‐aryl‐substituted 3‐pyrroline products are obtained in good yield and with high enantioselectivity. The application of the method to the concise formal synthesis of (+)‐trachelanthamidine is also demonstrated. Boc=tert‐butoxycarbonyl, M.S.=molecular sieves, TBDPS=

  快速反应：标题反应在5摩尔％的催化剂1的存在下进行，并在一小时内完成。以高收率和高对映选择性获得2-烷基和2-芳基取代的3-吡咯啉产物。还证明了该方法在简明形式的（+）-trachelanthamidine合成中的应用。Boc =叔丁氧羰基，MS =分子筛，TBDPS =叔丁基二苯基甲硅烷基。
• Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions
  作者：Yuan-Qing Fang、Eric N. Jacobsen

  DOI：10.1021/ja801344w

  日期：2008.4.1

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.
• Enantioselective Binaphthophosphepine-Promoted [3+2] Annulations of N-Ts- and N-DPP-Imines with Allenoates and 2-Butynoates
  作者：Nathalie Pinto、Nicolas Fleury-Brégeot、Angela Marinetti

  DOI：10.1002/ejoc.200800598

  日期：——

  The use of binaphthophosphepine 1a as a catalyst for the [3+2] cyclisation between allenoates or 2-butynoates andimines was investigated. The effects of the imine protecting group on both the catalytic activity and enantioselectivity were determined by comparing the behaviour of N-tosyl- and N-DPP-imines. The N-DPP-imines displayed lower reactivity, but afforded the desired pyrrolines in higher enantiomeric

  研究了双萘膦 1a 用作烯丙酸酯或 2-丁酸酯和亚胺之间 [3+2] 环化的催化剂。通过比较 N-甲苯磺酰基-和 N-DPP-亚胺的行为，确定亚胺保护基团对催化活性和对映选择性的影响。N-DPP-亚胺表现出较低的反应性，但以更高的对映体过量（73-92％ee）提供所需的吡咯啉。在温和条件下从最终的吡咯啉中除去 DPP 保护基团，得到相应的仲胺。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)