(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene | 166765-36-2

• 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: (2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene
• 英文别名: ethyl (3R,7aS)-5-oxo-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-6-carboxylate
• CAS: 166765-36-2
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: WLVOQWAJJPFVPX-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene 在 N,N-二甲基丙烯基脲 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3S,4R)-4-Benzyl-4-ethoxycarbonyl-2-methoxycarbonyl-3-methoxycarbonylmethyl-5-oxopyrrolidine
  参考文献：
  名称：

  Direct versatile route to conformationally constrained glutamate analogues

  摘要：

  从(S)-焦谷氨酸中很容易获得构象受限的新型谷氨酸类似物；利用双环内酰胺模板，可以对吡咯烷环进行非对映控制和顺序修饰，从而获得多种谷氨酸和类缬氨酸类似物；根据杂环上的远程取代基的性质，可以观察到 C(2)H-C(3)H 耦合常数的变化，这与环构象的改变是一致的。

  DOI：

  10.1039/a708429c
• 作为产物：
  描述：

  (3R,7aS)-5-Oxo-3-phenyl-6-phenylselanyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid ethyl ester 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以84%的产率得到(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene
  参考文献：
  名称：

  Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions

  摘要：

  The alpha,beta-unsaturated bicyclic lactams 3a,c, prepared from (S)-pyroglutamic acid, are useful substrates for cycloaddition reactions, giving excellent regio-and diastereocontrol; however, lactam 3c has very superior reactivity with several dienes and dipoles under mild reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00740-0

文献信息

• Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid
  作者：Emilie L. Bentz、Rajesh Goswami、Mark G. Moloney、Susan M. Westaway

  DOI：10.1039/b503994k

  日期：——

  Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala-Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In this strategy, the bicyclic lactam system not only controls, but also facilitates the determination of

  衍生自焦谷氨酸的双环内酰胺为合成赖氨酸，鸟氨酸和谷氨酰胺的构象受限的类似物以及Ala-Ala二肽类似物提供了有用的支架。氨基醇和羧酸衍生物可从常见的中间体获得。在这种策略中，双环内酰胺系统不仅控制，而且还有助于确定合成中间体的立体化学。
• Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines
  作者：Lawrence Harris、Martin Gilpin、Amber L. Thompson、Andrew R. Cowley、Mark G. Moloney

  DOI：10.1039/c5ob00648a

  日期：——

  cycloaddition of substituted diaryldiazo compounds onto bicyclic unsaturated lactams derived from pyroglutamic acid efficiently leads to highly functionalised azatricyclononanes. The products are readily elaborated to deprotected pyroglutamate derivatives, providing rapid access to conformationally constrained amino acids and their analogues. Preliminary assessment of antibacterial activity against

  取代的二芳基重氮化合物在衍生自焦谷氨酸的双环不饱和内酰胺上的未催化环加成有效地导致高度官能化的氮杂三环壬烷。该产品易于修饰成脱保护的焦谷氨酸衍生物，可快速获得构象受限的氨基酸及其类似物。对一种革兰氏阳性和一种革兰氏阴性生物的抗菌活性的初步评估表明，在某些情况下，其疗效很高。
• Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones
  作者：Philip W. H. Chan、Ian F. Cottrell、Mark G. Moloney

  DOI：10.1039/b106782f

  日期：2001.11.15

  The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to α,β-unsaturated bicyclic lactam 1a gave the corresponding β-amino products 9a–g in good yield and excellent diastereoselectivity. These products can be manipulated to afford enantiopure β-aminopyrrolidinones of potential application as conformationally-constrained, substituted glutamate templates of well-defined stereochemistry.

  活性氮亲核试剂（如羟胺和肼衍生物）与α,β-不饱和双环内酰胺1a 的共轭加成得到相应的β-氨基产物9a–g，产率良好，非对映选择性极佳。这些产品可以被操纵以提供对映体纯β-氨基吡咯烷酮的潜在应用作为构象限制，取代的谷氨酸模板的明确的立体化学。
• Functionalised pyrrolidinones by conjugate addition of stabilised enolates and Reformatsky reagents
  作者：James Dyer、Steve Keeling、Mark G Moloney

  DOI：10.1016/0040-4039(96)00849-0

  日期：1996.6

  The α,β-unsaturated lactam 1b has been found to readily undergo conjugate addition reactions with a range of stabilised carbon nucleophiles and Reformatsky reagents under mild conditions in good yield with high diastereoselectivity. This method provides a simple and versalile approach to highly functionalised pyrrolidinones.

  已经发现，α，β-不饱和内酰胺1b在温和的条件下容易地与一系列稳定的碳亲核试剂和Reformatsky试剂进行共轭加成反应，并具有高产率和非对映选择性。该方法为高度官能化的吡咯烷酮提供了一种简单且通用的方法。
• Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid
  作者：Rajesh Goswami、Mark G. Moloney

  DOI：10.1039/a906297a

  日期：——

  Conformationally constrained lysine and ornithine analogues, and an L-Ala-L-Ala dipeptide analogue, are available from pyroglutamic acid.

  从焦谷氨酸可以得到构象受限的赖氨酸和鸟氨酸类似物，以及L-丙氨酰-L-丙氨酰二肽类似物。