(4S)-4-N-benzylamino-5-phenyl-2-methyl-2-trans-pentenoic acid, ethyl ester | 244033-84-9

• 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-methyl-2-trans-pentenoic acid, ethyl ester
• 英文别名: ethyl (E,4S)-4-(benzylamino)-2-methyl-5-phenylpent-2-enoate
• CAS: 244033-84-9
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: HYFJQDPBBZACIT-BBKFTCMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-methyl-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 20.33h， 生成 ethyl (3S,3aR,4R,5S,7aR)-2,3-dibenzyl-4,5-dimethyl-1-oxo-3,3a,5,7a-tetrahydroisoindole-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：

  三乙基2-膦酰基丙酯 在 potassium tert-butylate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (4S)-4-N-benzylamino-5-phenyl-2-methyl-2-trans-pentenoic acid, ethyl ester
  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

文献信息

• 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.