(3S)-3-([(benzyloxy)carbonyl]amino)-4-pentenoic acid | 281208-45-5

• 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: (3S)-3-([(benzyloxy)carbonyl]amino)-4-pentenoic acid
• 英文别名: (3S)-3-(phenylmethoxycarbonylamino)pent-4-enoic acid
• CAS: 281208-45-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: TXTKPBMYCVEXLN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-([(benzyloxy)carbonyl]amino)-4-pentenoic acid 在 copper(l) iodide 、 碘 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 benzyl (2S,3S)-2-cyclohexylmethyl-5-oxotetrahydrofuran-3-ylcarbamate
  参考文献：
  名称：

  Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids

  摘要：

  The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-gamma-hydroxy-beta-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino1-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00033-1
• 作为产物：
  描述：

  tert-butyl-(3S)-3-{[(benzyloxy)carbonyl]amino}-4-pentenoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(3S)-3-([(benzyloxy)carbonyl]amino)-4-pentenoic acid
  参考文献：
  名称：

  Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids

  摘要：

  The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-gamma-hydroxy-beta-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino1-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00033-1

文献信息

• Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones
  作者：Brad E. Sleebs、Nghi H. Nguyen、Andrew B. Hughes

  DOI：10.1016/j.tet.2013.05.016

  日期：2013.7

  The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
• Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids
  作者：Giuliano Delle Monache、Domenico Misiti、Patrizia Salvatore、Giovanni Zappia

  DOI：10.1016/s0957-4166(00)00033-1

  日期：2000.3

  The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-gamma-hydroxy-beta-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino1-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.