ethyl 3-(4-chlorophenyl)-2-cyano-2-phenylpropanoate | 1244978-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 3-(4-chlorophenyl)-2-cyano-2-phenylpropanoate
• CAS: 1244978-26-4
• 化学式: C₁₈H₁₆ClNO₂
• 分子量: 313.784
• InChiKey: QEFVVOCQPNNPEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-chlorophenyl)-2-cyano-2-phenylpropanoate 在 氨 、 氢气 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant

  摘要：

  The design, synthesis, and binding activity of ring constrained analogs of the acyclic cannabinoid-1 receptor (CB1R) inverse agonist taranabant 1 are described. The initial inspiration for these taranabant derivatives was its conformation 1a, determined by (1)H NMR, X-ray, and molecular modeling. The constrained analogs were all much less potent than their acyclic parent structure. The results obtained are discussed in the context of a predicted binding of 1 to a homology model of CB1R. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.127
• 作为产物：
  描述：

  4-氯苄溴 、 苯基氰基乙酸乙酯 在 1,3-二甲基-2-咪唑啉酮 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 3-(4-chlorophenyl)-2-cyano-2-phenylpropanoate
  参考文献：
  名称：

  Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant

  摘要：

  The design, synthesis, and binding activity of ring constrained analogs of the acyclic cannabinoid-1 receptor (CB1R) inverse agonist taranabant 1 are described. The initial inspiration for these taranabant derivatives was its conformation 1a, determined by (1)H NMR, X-ray, and molecular modeling. The constrained analogs were all much less potent than their acyclic parent structure. The results obtained are discussed in the context of a predicted binding of 1 to a homology model of CB1R. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.127

文献信息

• Parallel Kinetic Resolution through Palladium-Catalyzed Enantioselective Cycloimidoylation: En Route to Divergent <i>N</i>-Heterocycles Bearing a Quaternary Stereogenic Center
  作者：Xilong Wang、Yu Luo、Jing Li、Chaoqin Wang、Qianwen Liu、Yimiao He、Shuang Luo、Qiang Zhu

  DOI：10.1021/acscatal.2c04941

  日期：2022.12.16

  An example of a parallel kinetic resolution catalyzed by palladium to produce enantioenriched five- and six-membered N-heterocycles in one pot was developed. Dihydroisoquinolines and 1H-isoindoles containing a quaternary stereogenic center were obtained from racemic isocyanides in high yields with good enantioselectivities under mild conditions. A 6,6′-dipropyl substituted SPINOL-derived phosphoramidite

  开发了一个由钯催化的平行动力学拆分示例，以在一锅中生产对映体富集的五元和六元N-杂环。在温和条件下，从外消旋异氰化物中以高产率和良好的对映选择性获得了含有季立体异构中心的二氢异喹啉和 1 H-异吲哚。6,6'-二丙基取代的 SPINOL 衍生的亚磷酰胺被用作钯催化剂的手性配体，导致区域发散和立体特异性环亚胺酰化。密度泛函理论 (DFT) 计算揭示了 C(SP 2 )–H 亚氨基化环化过程中区域选择性和对映选择性的来源。