α-(nitromethyl)chalcone | 143008-58-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: α-(nitromethyl)chalcone
• 英文别名: (E)-2-nitromethyl-1,3-diphenyl-2-en-1-one；(E)-2-(nitromethyl)-1,3-diphenylprop-2-en-1-one
• CAS: 143008-58-6
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: VGNRASPJYVVDDL-RVDMUPIBSA-N

物化性质

• 沸点：
  449.8±45.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  α-(nitromethyl)chalcone 在 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 2.17h， 生成 (R)-2-Methylene-1,3-diphenyl-heptan-1-one
  参考文献：
  名称：

  Asymmetric synthesis of 3-substituted 2-exo-methylenealkanones by addition-elimination reaction using a chiral leaving group and organometallic nucleophiles

  摘要：

  A novel diastereodifferentiating addition-elimination reaction of (S)-2-[[2-(methoxymethyl)-1-pyrrolidinyl]methyl]-2-alken-1-ones with organometallic reagents such as organocuprates and organozincates afforded optically active 3-substituted 2-methylenealkanones with high enantiomeric purity. The enantiomeric excess (ee) of the products in this asymmetric induction reaction involving 1,5-transfer of stereogenicity was highly dependent on the structure of the enone substrates and the type of organometallic reagents, chiral auxiliaries, and added Lewis acids: (i) the use of lithium diorganocuprates (R2CuLi) led to the highest ee's, (ii) in the reaction with R2CuLi the ee decreased in the following order by varying their structure of the main framework of the enones, cycloheptenones (96-97% ee) > cyclohexenones (95% ee) > cyclopentenones (82-85% ee) > acyclic enones (55-70% ee), (iii) the addition of LiBr as the external Lewis acid in the reaction with R2CuLi did not affect the ee, whereas that of ZnBr2 or MgBr2 decreased the ee by 5% or considerably more, respectively, and (iv) the existence of the methoxy oxygen atom in the chiral auxiliary was essential to achieve high ee's. The origin of the observed high and low ee's was rationalized by considering plausible transition state models.

  DOI：

  10.1021/jo00044a026
• 作为产物：
  描述：

  (E)-2-(bromomethyl)-1,3-diphenylprop-2-en-1-one 在 silver(I) nitrite 作用下， 以 乙醚 为溶剂， 以53%的产率得到α-(nitromethyl)chalcone
  参考文献：
  名称：

  一种有机亚硝酸根供体及其制备方法与医药用途

  摘要：

  本发明涉及药物化学领域，具体涉及含有1‑硝甲基‑2‑苯基乙烯骨架的有机亚硝酸根供体化合物(通式I和通式II所示的结构)，其制备方法，以及这些化合物的药用组合物在预防或治疗脑缺血、心肌缺血和肺动脉高压中的医药用途。

  公开号：

  CN112209834B

文献信息

• Design, Synthesis, and Biological Evaluation of Organic Nitrite (NO₂^–) Donors as Potential Anticerebral Ischemia Agents
  作者：Jianbing Wu、Wei Yin、Zhangjian Huang、Yinqiu Zhang、Jian Jia、Huimin Cheng、Fenghua Kang、Kai Huang、Tao Sun、Jide Tian、Xiaojun Xu、Yihua Zhang

  DOI：10.1021/acs.jmedchem.1c00282

  日期：2021.8.12