ethyl -5-cyclohexyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-pentenoate | 114371-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl -5-cyclohexyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-pentenoate
• 英文别名: ethyl (2E,4S)-4-<(tert-butoxycarbonyl)amino>-5-cyclohexyl-2-pentenoate；Ethyl 4(S)-t-Butyloxycarbonylamino-5-cyclohexylpent-2(E)-enoate；ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-cyclohexyl-2-pentenoate；ethyl (E,4S)-5-cyclohexyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pent-2-enoate
• CAS: 114371-49-2
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: KNTPEEKEUFGTGV-AYJWMTRPSA-N

物化性质

• 沸点：
  438.4±38.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl -5-cyclohexyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-pentenoate 在 吡啶 、 盐酸 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 40.75h， 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：

  S-(-)-2-N-BOC-3-环己基-1-丙醇 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.5h， 生成 ethyl -5-cyclohexyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-pentenoate
  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。
• Aminomethyl-peptide, Verfahren zur Herstellung und ihre Verwendung in Arzneimitteln
  申请人：BAYER AG

  公开号：EP0356796A2

  公开（公告）日：1990-03-07

  Die Erfindung betrifft neue renininhibitorische Aminomethyl-peptide der allgemeinen Formel (I) in welcher A, B, D, E, F, R1, R2, R3 und R4 die in der Beschreibung angegebene Bedeutung haben, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln, insbesondere in kreislaufbeeinflussenden Arzneimitteln.

  本发明涉及通式(I)的新型肾素抑制氨甲基肽。 中 A、B、D、E、F、R1、R2、R3 和 R4 的含义，以及它们的制备工艺和在药物中，特别是在影响循环的药物中的用途。
• 1,2,4-Triazolo[4,3-a]pyrazine derivatives with human renin inhibitory activity. 3. Synthesis and biological properties of aminodeoxystatine and difluorostatone derivatives
  作者：Robert H. Bradbury、Janet E. Rivett

  DOI：10.1021/jm00105a022

  日期：1991.1

  Two series of 1,2,4-triazolo[4,3-a]pyrazine derivatives with human renin inhibitory activity have been synthesized which incorporate the transition-state mimetics (3S,4S)- and (3R,4S)-5-cyclohexyl-3,4-diaminopentanoic acid ((S)- and (R)-CDAPA), and (4S)-4-amino-5-cyclohexyl-2,2-difluoro-3-oxopentanoic acid (ACDFOPA). Several compounds in these series, for example 13a, 19c, and 19f, were highly potent inhibitors of partially purified human renin (IC50 values of 3.9, 1.6, and 1.4 nM, respectively). The ACDFOPA-based compounds 19c and 19f contain no natural amino acid fragments and have molecular weights which compare well with those of previously reported inhibitors to nanomolar in vitro potency. When administered intravenously to anesthetized, sodium-depleted marmosets at doses of 3 mg/kg, compounds 13a and 19c caused a marked reduction in mean arterial pressure, but in the same animal model at 30 mg/kg, oral activity was not seen.
• 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
• HENNING, ROLF;BENZ, GUNTER;BENDER, WOLFGANG;STASCH, JOHANNES-PETER;KNORR,+
  作者：HENNING, ROLF、BENZ, GUNTER、BENDER, WOLFGANG、STASCH, JOHANNES-PETER、KNORR,+

  DOI：——

  日期：——