isopropyl 3-nitropent-2-enoate | 1431387-47-1

• 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: isopropyl 3-nitropent-2-enoate
• CAS: 1431387-47-1
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: AROYNVRGLVQVPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  isopropyl 3-nitropent-2-enoate 在 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、202.66 kPa 条件下， 反应 38.0h， 生成 isopropyl 3-ethyl-5-oxopiperazine-2-carboxylate
  参考文献：
  名称：

  β-Nitroacrylates as key building blocks for the synthesis of alkyl 3-substituted 5-oxopiperazine-2-carboxylates under fully heterogeneous conditions

  摘要：

  Substituted piperazines are important heterocycles possessing wide and important biological activities. Herein we report a new easy synthetic approach for preparation of alkyl 3-substituted 5-oxopiperazine-2-carboxylates using beta-nitroacrylates as key starting materials.

  DOI：

  10.1007/s00706-012-0895-1

文献信息

• A new fully heterogeneous synthesis of pyrrole-2-acetic acid derivatives
  作者：Serena Gabrielli、Ludovica Ciabattoni、Susanna Sampaolesi、Roberto Ballini、Alessandro Palmieri

  DOI：10.1039/c6ra05348c

  日期：——

  Herein, we present a new general and efficient protocol to synthesize pyrrole-2-acetic acid derivatives starting from pyrroles and β-nitroacrylates, under fully heterogeneous conditions.

  在本文中，我们提出了一种新的通用且有效的方案，可以在完全非均相的条件下从吡咯和β-硝基丙烯酸酯开始合成吡咯-2-乙酸衍生物。
• Stereoselective Synthesis of Functionalized Chiral 2-Nitrocyclohexanecarboxylic Esters<i>via</i>Catalytic Dienamine Addition to β-Substituted β-Nitroacrylates
  作者：Elisabetta Massolo、Maurizio Benaglia、Rita Annunziata、Alessandro Palmieri、Giuseppe Celentano、Alessandra Forni

  DOI：10.1002/adsc.201301074

  日期：2014.2.10

  AbstractA metal‐free stereoselective catalytic addition of in situ generated dienamine to β‐nitroacrylates has been developed. Starting from simple α,β‐unsaturated ketones, highly functionalized chiral β‐nitrocyclohexanecarboxylic esters were obtained in a single step, in good yields and up to 98% ee. By an unprecedented mechanistic pathway, starting from the synthetically readily available E‐nitroacrylate, the present methodology allowed us to obtain as major product the isomer bearing a cis relative disposition between the nitro and the ester groups, which is not accessible via a classical Diels–Alder reaction.magnified image