(+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone | 253599-39-2

• 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: (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone
• 英文别名: (+)-cis-1-allyl-3-(R)-benzyloxy-4-(S)-(2,2-dimethyl-[1,3]dioxolan-4-(S)-yl)-azetidin-2-one；(3R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxy-1-prop-2-enylazetidin-2-one
• CAS: 253599-39-2
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: BDSYEKIXPMPNCP-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone 在 sodium periodate 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 methyl (2R)-2-[(3aS,6S,6aS)-1-methyl-3,3a,4,5,6,6a-hexahydropyrrolo[3,4-c][1,2]oxazol-6-yl]-2-phenylmethoxyacetate
  参考文献：
  名称：

  通过 2-氮杂环丁酮系链烯醛的分子内硝酮-烯烃环加成对新型稠合或桥连三环 β-内酰胺的非对映选择性途径 - 碳消炎痛和环状 β-氨基酸衍生物的合成应用

  摘要：

  通过使用容易获得的单环 2-氮杂环丁酮链烯醛的分子内硝酮-烯烃环加成 (INAC) 反应作为关键合成步骤，开发了一种方便的、区域和立体选择性的直接制备光学纯异常稠合或桥连三环 β-内酰胺的途径. 环加成的区域选择性可以通过将烯烃取代基从 N1 移动到 2-氮杂环丁酮环上的 C3 来调节。此外，在制备的不同类型三环系统的代表性实例上测试了一些简单、有趣的转化，以证明它们作为制备不同多官能化合物的中间体的潜力，包括碳酰苯甲胺衍生物和相关的含有中等大小的非常规双环系统。与β-内酰胺核融合的环，以及几种类型的环状β-氨基酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200400792
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone
  参考文献：
  名称：

  Asymmetric synthesis of 4-formyl-1-(ω-haloalkyl)-β-lactams and their transformation to functionalized piperazines and 1,4-diazepanes

  摘要：

  Chiral piperazine and 1,4-diazepane annulated beta-lactams, prepared from the corresponding (3R,4S)-4-imidoyl-1-(omega-haloalkyl)azetidin-2-ones through reduction with sodium borohydride in ethanol, were transformed into novel methyl (R)-alkoxy-[(S)-piperazin-2-yl]acetates and methyl (R)-alkoxy-[(S)-1,4-diazepan-2-yl]acetates upon treatment with hydrogen chloride in methanol. On the other hand, bromination of (3R,4R)-1-allyl-4-formyl-beta-lactams and (3R,4S)-1-allyl-4-imidoyl-beta-lactams in dichloromethane, followed by sodium borohydride reduction of the resulting dibrominated azetidin-2-ones in ethanol, did not afford the envisaged bicyclic beta-lactams but unexpectedly furnished (3R,4S)-1-(2-bromo-2-propenyl)azetidin-2-ones instead. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.136

文献信息

• Synthesis of novel 4-(5'-pyrrolidinyl)-β-lactams
  作者：Ronald Grigg、Mark Thornton-Pett、Juan Xu、Long-He Xu

  DOI：10.1016/s0040-4020(99)00867-4

  日期：1999.11

  The synthesis of novel 4-(5'-pynolidinyl)-beta-lactams from imines derived from 4-formyl-beta-lactams and alpha-amino esters via cascade imine-->azomethine ylide-->1,3-dipolar cycloaddition reactions is described. These cascades are endo-specific, exhibit facial stereoselectivity and occur in good to excellent yields. (C) 1999 Elsevier Science Ltd. Ail rights reserved.
• Asymmetric synthesis of 4-formyl-1-(ω-haloalkyl)-β-lactams and their transformation to functionalized piperazines and 1,4-diazepanes
  作者：Stijn Dekeukeleire、Matthias D’hooghe、Matthieu Vanwalleghem、Willem Van Brabandt、Norbert De Kimpe

  DOI：10.1016/j.tet.2011.09.136

  日期：2012.12

  Chiral piperazine and 1,4-diazepane annulated beta-lactams, prepared from the corresponding (3R,4S)-4-imidoyl-1-(omega-haloalkyl)azetidin-2-ones through reduction with sodium borohydride in ethanol, were transformed into novel methyl (R)-alkoxy-[(S)-piperazin-2-yl]acetates and methyl (R)-alkoxy-[(S)-1,4-diazepan-2-yl]acetates upon treatment with hydrogen chloride in methanol. On the other hand, bromination of (3R,4R)-1-allyl-4-formyl-beta-lactams and (3R,4S)-1-allyl-4-imidoyl-beta-lactams in dichloromethane, followed by sodium borohydride reduction of the resulting dibrominated azetidin-2-ones in ethanol, did not afford the envisaged bicyclic beta-lactams but unexpectedly furnished (3R,4S)-1-(2-bromo-2-propenyl)azetidin-2-ones instead. (C) 2011 Elsevier Ltd. All rights reserved.
• Diastereoselective Route to Novel Fused or Bridged Tricyclic β-Lactams through Intramolecular Nitrone-Alkene Cycloaddition of 2-Azetidinone-Tethered Alkenylaldehydes - Synthetic Applications to Carbacephams and Cyclic β-Amino Acid Derivatives
  作者：Benito Alcaide、Elena Sáez

  DOI：10.1002/ejoc.200400792

  日期：2005.4

  tricyclic systems prepared, in order to demonstrate their potential as intermediates in the preparation of differently polyfunctionalized compounds, including carbacepham derivatives and related unconventional bicyclic systems containing medium-sized rings fused to the β-lactam nucleus, as well as several types of cyclic β-amino acid derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  通过使用容易获得的单环 2-氮杂环丁酮链烯醛的分子内硝酮-烯烃环加成 (INAC) 反应作为关键合成步骤，开发了一种方便的、区域和立体选择性的直接制备光学纯异常稠合或桥连三环 β-内酰胺的途径. 环加成的区域选择性可以通过将烯烃取代基从 N1 移动到 2-氮杂环丁酮环上的 C3 来调节。此外，在制备的不同类型三环系统的代表性实例上测试了一些简单、有趣的转化，以证明它们作为制备不同多官能化合物的中间体的潜力，包括碳酰苯甲胺衍生物和相关的含有中等大小的非常规双环系统。与β-内酰胺核融合的环，以及几种类型的环状β-氨基酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)