4-[benzyl-(4-oxo-pent-2-enoyl)-amino]-5-methylhex-2-enoic acid ethyl ester | 497830-80-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-[benzyl-(4-oxo-pent-2-enoyl)-amino]-5-methylhex-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4S)-4-[benzyl-[(E)-4-oxopent-2-enoyl]amino]-5-methylhex-2-enoate
• CAS: 497830-80-5
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: QUHKUQDHIPLZLA-JJFBIQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[benzyl-(4-oxo-pent-2-enoyl)-amino]-5-methylhex-2-enoic acid ethyl ester 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 96.0h， 生成 ethyl (3S,3aR,4R,7aR)-2-benzyl-6-methyl-5-oxido-1-oxo-3-propan-2-yl-3a,4,7,7a-tetrahydro-3H-pyrrolo[3,4-c]pyridin-5-ium-4-carboxylate
  参考文献：
  名称：

  α，β-不饱和肟在分子内[4 + 2]环加成反应中的有趣行为。

  摘要：

  [结构：见正文]探索了使用α，β-不饱和肟的分子内[4 + 2]环加成反应。反应在异常容易的条件下进行以提供硝酮。后者随后用DMAD反应，得到[3 + 2]环加成产物。

  DOI：

  10.1021/ol049640n
• 作为产物：
  描述：

  N-BOC-2(S)-2-AMINO-3-METHYL-BUTAL聽 在 N-羟基-7-氮杂苯并三氮唑 、 potassium tert-butylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-[benzyl-(4-oxo-pent-2-enoyl)-amino]-5-methylhex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

  摘要：

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01711-2

文献信息

• An intramolecular oxo Diels–Alder approach to 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters
  作者：William V Murray、Pranab K Mishra、Ignatius J Turchi、Dorota Sawicka、Amy Maden、Sengen Sun

  DOI：10.1016/j.tet.2003.04.007

  日期：2003.11

  The diastereoselective synthesis of a series of 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters via an oxo Diels-Alder reaction is described. Ab initio calculations predicted the products of the exo cycloaddition to be the thermodynamic products while the products resulting from the endo cycloaddition were predicted to be the kinetic products. The calculations were born out by experimental data. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction
  作者：William V. Murray、Pranab K. Mishra、Sengen Sun、Amy Maden

  DOI：10.1016/s0040-4039(02)01711-2

  日期：2002.10

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Interesting Behavior of α,β-Unsaturated Oximes in Intramolecular [4 + 2] Cycloaddition Reactions
  作者：David François、Amy Maden、William V. Murray

  DOI：10.1021/ol049640n

  日期：2004.6.1

  [structure: see text] Intramolecular [4 + 2] cycloaddition using alpha,beta-unsaturated oximes was explored. The reactions proceeded under unusually facile conditions to furnish the nitrones. The latter were subsequently reacted with DMAD to afford [3 + 2] cycloaddition products.

  [结构：见正文]探索了使用α，β-不饱和肟的分子内[4 + 2]环加成反应。反应在异常容易的条件下进行以提供硝酮。后者随后用DMAD反应，得到[3 + 2]环加成产物。