methyl (4S-trans)-4,5-dihydro-4-cyclohexylmethyl-2-phenyloxazoline-5-acetate

• 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: methyl (4S-trans)-4,5-dihydro-4-cyclohexylmethyl-2-phenyloxazoline-5-acetate
• 英文别名: methyl 2-[(4S,5S)-4-(cyclohexylmethyl)-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]acetate
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: GAAZMQIKXKJIHC-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯 在 吡啶 、 盐酸 、 ruthenium trichloride 、 sodium periodate 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 碳酸氢钠 、 potassium carbonate 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 反应 73.92h， 生成 methyl (4S-trans)-4,5-dihydro-4-cyclohexylmethyl-2-phenyloxazoline-5-acetate
  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

• US6127546A
  申请人：——

  公开号：US6127546A

  公开（公告）日：2000-10-03
• 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.