(E)-(S)-4-Amino-6-methyl-hept-2-en-1-ol | 298208-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(S)-4-Amino-6-methyl-hept-2-en-1-ol
• 英文别名: (E,4S)-4-amino-6-methylhept-2-en-1-ol
• CAS: 298208-81-8
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: MSOQNVPAWMQGLX-MPJRPATESA-N

物化性质

• 沸点：
  240.7±28.0 °C(predicted)
• 密度：
  0.917±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-Amino-6-methyl-hept-2-en-1-ol 在 吡啶 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 38.0h， 生成 (4S-trans)-4,5-dihydro-4-isobutyl-2-phenyl-5-vinyl-oxazoline
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 盐酸 、 三氟化硼乙醚 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 5.25h， 生成 (E)-(S)-4-Amino-6-methyl-hept-2-en-1-ol
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r

文献信息

• Stereoselective γ-lactam synthesis via palladium-catalysed intramolecular allylation
  作者：Donald Craig、Christopher J. T. Hyland、Simon E. Ward

  DOI：10.1039/b504731e

  日期：——

  A novel route to the synthesis of 3-(tolylsulfonyl)-4,5-cis-disubstituted γ-lactams using a diastereoselective palladium-catalysed intramolecular allylation of amino acid-derived allylic carbonates has been developed.

  开发了一种新方法，通过二对映体选择性的钯催化环内烯丙基化反应，以合成3-(甲苯磺酰基)-4,5-顺式二取代的γ-内酯，该反应以氨基酸衍生的烯丙基碳酸酯为底物。
• Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)
  作者：Kee-Young Lee、Yong-Hyun Kim、Min-Sung Park、Chang-Young Oh、Won-Hun Ham

  DOI：10.1021/jo991065r

  日期：1999.12.1

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.