1,1-dimethylethyl -<1-(cyclohexylmethyl)-4-hydroxy-2-butenyl>carbamate | 114371-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1-dimethylethyl -<1-(cyclohexylmethyl)-4-hydroxy-2-butenyl>carbamate
• 英文别名: (4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-2-penten-1-ol；4(S)-t-Butyloxycarbonylamino-5-cyclohexylpent-2(E)-enol；1,1-dimethylethyl (S-(E))-[1-(cyclohexylmethyl)-4-hydroxy-2-butenyl]carbamate；tert-butyl N-[(E,2S)-1-cyclohexyl-5-hydroxypent-3-en-2-yl]carbamate
• CAS: 114371-50-5
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: WGCIIYXDZNRHRA-DNGMOHDESA-N

物化性质

• 沸点：
  421.9±38.0 °C(predicted)
• 密度：
  1.012±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl -<1-(cyclohexylmethyl)-4-hydroxy-2-butenyl>carbamate 在 吡啶 、 盐酸 、 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 38.5h， 生成 (4S-trans)-4,5-dihydro-4-cyclohexylmethyl-2-phenyl-5-vinyloxazoline
  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：

  2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.75h， 生成 1,1-dimethylethyl -<1-(cyclohexylmethyl)-4-hydroxy-2-butenyl>carbamate
  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

• Peptidyl-1-amino-2,4-diols
  申请人：Abbott Laboratories

  公开号：US04725584A1

  公开（公告）日：1988-02-16

  The invention relates to renin inhibiting compounds of the formula ##STR1## wherein A is an N-protecting group; R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are independently selected from loweralkyl or lipophilic or aromatic amino acid side chains; and R.sub.4 is hydrogen, loweralkyl, loweralkylmercapto or loweralkylsulfonyl.

  该发明涉及化学式##STR1##中的抑制肾素化合物，其中A是N-保护基团；R.sub.1、R.sub.2、R.sub.3和R.sub.5分别选自较低的烷基或亲脂性或芳香族氨基酸侧链；而R.sub.4是氢、较低的烷基、较低的烷基硫醇或较低的烷基磺酰基。
• A study of the 3,3-sigmatropic rearrangement of chiral trichloroacetamidic esters
  作者：A. M. Doherty、B. E. Kornberg、M. D. Reily

  DOI：10.1021/jo00055a047

  日期：1993.1
• LULY, JAY R.;PLATTNER, JACOB J.;SHAM, HING L.
  作者：LULY, JAY R.、PLATTNER, JACOB J.、SHAM, HING L.

  DOI：——

  日期：——
• US4725584A
  申请人：——

  公开号：US4725584A

  公开（公告）日：1988-02-16
• 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.