2-benzyl-1-(4-chlorophenyl)prop-2-en-1-one | 1416358-60-5

• 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: 2-benzyl-1-(4-chlorophenyl)prop-2-en-1-one
• 英文别名: 2-Benzyl-1-(4-chlorophenyl)prop-2-en-1-one
• CAS: 1416358-60-5
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: OZNRMNDQEKNATH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-1-(4-chlorophenyl)prop-2-en-1-one 、 p-methoxybenzaldehyde 4-phenylsemicarbazone 在 polystyrene-supported TBD 、 Amberlyst A-15 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72 mg的产率得到3-(4-Chlorophenyl)-4,5-dihydro-N-phenyl-4-(phenylmethyl)-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands

  摘要：

  In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [S-35]-GTP gamma S binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure activity relationship. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.031
• 作为产物：
  描述：

  对氯苯甲酸 在 哌啶 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-benzyl-1-(4-chlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands

  摘要：

  In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [S-35]-GTP gamma S binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure activity relationship. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.031

文献信息

• Visible-light-enabled stereoselective synthesis of functionalized cyclohexylamine derivatives <i>via</i> [4 + 2] cycloadditions
  作者：Yi-Nan Lu、Chao Che、Guangjin Zhen、Xin Chang、Xiu-Qin Dong、Chun-Jiang Wang

  DOI：10.1039/d4sc00667d

  日期：2024.5.1

  An unprecedented intermolecular [4 + 2] cycloaddition of benzocyclobutylamines with α-substituted vinylketones, enabled by photoredox catalysis, has been developed. The current method enables facile access to highly functionalized cyclohexylamine derivatives that were otherwise inaccessible, in moderate to good yields with excellent diastereoselectivities. This protocol has some excellent features

  通过光氧化还原催化，苯并环丁基胺与 α-取代乙烯基酮发生前所未有的分子间 [4 + 2] 环加成反应。目前的方法能够以中等至良好的产率和优异的非对映选择性轻松获得原本无法获得的高度官能化的环己胺衍生物。该方案具有完整的原子经济性、良好的官能团兼容性、温和的反应条件以及整体氧化还原中性过程等优异的特点。此外，通过掺入手性磷酸（CPA）初步研究了这种环加成的不对称形式，并且可以有效地实现中等至良好的对映选择性和优异的非对映选择性。通过放大实验和精细加工来获得氨基醇和环丁烯衍生物，证明了合成应用。根据对照实验的结果，提出了合理的反应机理，阐明了反应途径。
• Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands
  作者：Vincent Gembus、Christophe Furman、Régis Millet、Roxane Mansouri、Philippe Chavatte、Vincent Levacher、Jean-François Brière

  DOI：10.1016/j.ejmech.2012.10.031

  日期：2012.12

  In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [S-35]-GTP gamma S binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure activity relationship. (C) 2012 Elsevier Masson SAS. All rights reserved.