(4S)-4-N-benzylamino-5-phenyl-2-trans-pentenoic acid, ethyl ester | 244033-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-4-N-benzylamino-5-phenyl-2-trans-pentenoic acid, ethyl ester
• 英文别名: 4-benzylamino-5-phenyl-pent-2-enoic acid ethyl ester；ethyl (E,4S)-4-(benzylamino)-5-phenylpent-2-enoate
• CAS: 244033-83-8
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: XIZQJHBIPYFNHJ-JKIKYLSZSA-N

物化性质

• 沸点：
  450.2±45.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-N-benzylamino-5-phenyl-2-trans-pentenoic acid, ethyl ester 在 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 12.33h， 生成 ethyl (3S,3aR,4R,5R,7aS)-2,3-dibenzyl-5-methyl-1-oxo-3a,4,5,7a-tetrahydro-3H-isoindole-4-carboxylate
  参考文献：
  名称：

  Diels−Alder Reactions of Amino Acid-Derived Trienes

  摘要：

  Triene precursors (1a-e, 2a-k) were constructed for substrate-controlled asymmetric Diels-Alder reactions. Boc-L-phenylalanal and Boc-L-valinal were condensed with triethyl phosphonoacetate or 2-phosphonopropionate to generate the alpha,beta-unsaturated esters as dienophiles. Removal of the Boc group to give free amines 4a-d, which after, or without N-benzylation, were treated with 3,5-hexadienoyl chloride to give 1a-e, or with 2,4-hexadienoyl chloride to afford 2a-f. The trienes 2g-i were prepared via reductive alkylation of amines 4a-i with 2,4-hexadienal. The secondary amide triene la failed to yield any Diels-Alder product when heated at 170 degrees C. The tertiary amide trienes 1b-e produced in refluxing toluene the major cycloaddition products that were cia-fused and derived from the exo transition states. Trienes 2a-k underwent surprisingly facile Diels-Alder reactions to produce the major trans-fused isomers that Were derived from the endo transition states. For trienes 2b-h and 2j,k, Diels-Alder reactions proceeded at room temperature. For the primary amide 2a, the Diels-Alder reaction proceeded smoothly in refluxing toluene. The tertiary amide triene 22 was constructed to have two electron-withdrawing ester substituents at the termini of the triene. The Diels-Alder reaction of 22 took place spontaneously at room temperature upon benzoylation of the secondary amine 21 and produced a single isomer derived from the endo transition state. 1,3-Allylic strain is discussed as an important factor in control of the diastereoselectivity.

  DOI：

  10.1021/jo990459f
• 作为产物：
  描述：

  BOC-PHE-甲氧基甲胺 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4S)-4-N-benzylamino-5-phenyl-2-trans-pentenoic 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.
• Diels−Alder Reactions of Amino Acid-Derived Trienes
  作者：William V. Murray、Sengen Sun、Ignatius J. Turchi、Frank K. Brown、A. Diane Gauthier

  DOI：10.1021/jo990459f

  日期：1999.8.1

  Triene precursors (1a-e, 2a-k) were constructed for substrate-controlled asymmetric Diels-Alder reactions. Boc-L-phenylalanal and Boc-L-valinal were condensed with triethyl phosphonoacetate or 2-phosphonopropionate to generate the alpha,beta-unsaturated esters as dienophiles. Removal of the Boc group to give free amines 4a-d, which after, or without N-benzylation, were treated with 3,5-hexadienoyl chloride to give 1a-e, or with 2,4-hexadienoyl chloride to afford 2a-f. The trienes 2g-i were prepared via reductive alkylation of amines 4a-i with 2,4-hexadienal. The secondary amide triene la failed to yield any Diels-Alder product when heated at 170 degrees C. The tertiary amide trienes 1b-e produced in refluxing toluene the major cycloaddition products that were cia-fused and derived from the exo transition states. Trienes 2a-k underwent surprisingly facile Diels-Alder reactions to produce the major trans-fused isomers that Were derived from the endo transition states. For trienes 2b-h and 2j,k, Diels-Alder reactions proceeded at room temperature. For the primary amide 2a, the Diels-Alder reaction proceeded smoothly in refluxing toluene. The tertiary amide triene 22 was constructed to have two electron-withdrawing ester substituents at the termini of the triene. The Diels-Alder reaction of 22 took place spontaneously at room temperature upon benzoylation of the secondary amine 21 and produced a single isomer derived from the endo transition state. 1,3-Allylic strain is discussed as an important factor in control of the diastereoselectivity.