(3S,4S)-3-methyl-1,4-diphenylazetidin-2-one | 195388-26-2

• 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: (3S,4S)-3-methyl-1,4-diphenylazetidin-2-one
• CAS: 195388-26-2
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: QURMOGAHPSNBBS-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (3R,4R)-3-hydroxy-3-methyl-1,4-diphenylazetidin-2-one 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 (3S,4S)-3-methyl-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  One-pot synthesis of (3R)-hydroxy-β-lactams via enolates of 2-tert-butyl-1,3-dioxolan-4-ones. Part 1

  摘要：

  Seebach's synthetic method of self-regeneration of stereocenters ''SRS'' has been applied to the addition reaction of diphenylimine 1 to the lithium enolates of (2S,5S)-2-(tert-butyl)-5-methyl-1,3-dioxolan-4-one 2a and of (2S,5S)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 2b. Variable 4S/4R mixtures of (3R)-S-hydroxy-beta-lactams 4a,b are obtained, depending on the reaction conditions. The induced enantioselectivity (ee) is very high, and the simple selectivity (exo-endo) is low. Overall, this appears a rather direct approach to chiral beta-lactams with full control of stereochemistry at C3. The stereoselective radical reduction of the stereoisomer (3R,4R)-E-4a afforded the homochiral C3,C4-monosubstituted beta-lactam (3S,4S)-Z-10. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00303-0

文献信息

• Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita–Baylis–Hillman Carbonates
  作者：You Zi、Markus Lange、Philipp Schüler、Sven Krieck、Matthias Westerhausen、Ivan Vilotijevic

  DOI：10.1055/s-0039-1691570

  日期：2020.4

  Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita–Baylis–Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization to produce analogues of biologically active β-lactams. The use of nearly equimolar quantities of the starting materials make this method efficient and straightforward.

  通过对苯胺进行对映选择性烯丙基化反应制备富含对映体的β-内酰胺，随后通过碱促进的环化反应得到。所得的3-亚甲基氮杂环丙酮可通过对映选择性官能化反应产生生物活性β-内酰胺类似物。该方法使用接近等摩尔量的起始原料使得该方法高效且简单。
• Asymmetric synthesis of trans and cis β-lactams
  作者：Manfred Braun、Hubert Sacha、Dietmar Galle、Abdullah El-Alali

  DOI：10.1016/0040-4039(95)00772-5

  日期：1995.6

  of doubly deprotonated triphenylglycol propionate 4a and imines 1 leads to the formation of trans β-lactams 5 in a diastereoselective and enantioselective manner (85 to > 97% e.e.). On the other hand, the lithium enolates of the propionates 4b,c, derived from triphenylglycol as well, afford predominantly cis 2-azetidinones 6 in 87 to > 97% e.e.

  双去质子化丙酸三苯二醇酯4a和亚胺1的缩合导致以非对映选择性和对映选择性的方式形成反式β-内酰胺5（ee介于85％到97％以上）。另一方面，也衍生自三苯乙二醇的丙酸酯4b，c的烯醇锂主要在87％到> 97％ee的范围内提供顺式2-氮杂环丁酮6
• Asymmetric synthesis of trans- β -lactams through TiCl4-mediated addition to imines.
  作者：Cesare Gennari、Isabella Venturini、Gabriele Gislon、Giuliana Schimperna

  DOI：10.1016/s0040-4039(00)95693-4

  日期：1987.1
• One-pot synthesis of (3R)-hydroxy-β-lactams via enolates of 2-tert-butyl-1,3-dioxolan-4-ones. Part 1
  作者：Gaetano Barbaro、Arturo Battaglia、Andrea Guerrini、Carlo Bertucci

  DOI：10.1016/s0957-4166(97)00303-0

  日期：1997.8

  Seebach's synthetic method of self-regeneration of stereocenters ''SRS'' has been applied to the addition reaction of diphenylimine 1 to the lithium enolates of (2S,5S)-2-(tert-butyl)-5-methyl-1,3-dioxolan-4-one 2a and of (2S,5S)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 2b. Variable 4S/4R mixtures of (3R)-S-hydroxy-beta-lactams 4a,b are obtained, depending on the reaction conditions. The induced enantioselectivity (ee) is very high, and the simple selectivity (exo-endo) is low. Overall, this appears a rather direct approach to chiral beta-lactams with full control of stereochemistry at C3. The stereoselective radical reduction of the stereoisomer (3R,4R)-E-4a afforded the homochiral C3,C4-monosubstituted beta-lactam (3S,4S)-Z-10. (C) 1997 Elsevier Science Ltd.