文拉法辛杂质4 | 29903-09-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 文拉法辛杂质4
• 英文名称: 1,3-bis(4-methoxyphenyl)acetone
• 英文别名: 1,3-bis(4-methoxyphenyl)propan-2-one；1,3-bis(4-methoxyphenyl)-2-propanone
• CAS: 29903-09-1
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: CDAXBXJOPWBMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  文拉法辛杂质4 在 氢溴酸 、 potassium carbonate 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 16.0h， 生成 1,3-bis<4-(benzyloxy)phenyl>propan-2-one
  参考文献：
  名称：

  具有收敛腔内功能的大型水溶性环芳烃

  摘要：

  新的三环间隔基很容易通过取代的二苄基酮的四倍Mannich反应获得，被引入到一系列十个H 2 O可溶性环烷中，它们具有宽敞的预组织空腔结合位点。这些间隔基提供了H 2 O溶解性，而胺或冠醚官能团的位置远离环烷酮腔，同时在腔内以精确的几何阵列定向官能团（例如酮基或OH基）。通过非极性和特定极性官能团相互作用的组合，环烷被设计为包括有机底物。三位点受体18的X射线晶体结构分析具有一个潜在的中性分子和两个阳离子结合位点的分子显示出一个大的矩形开放腔，尺寸约为9×14Å，两个会聚的CO基团的O原子之间的间距为9.7Å。尽管有结合位点的预组织，但结合了两个新间隔基的环烷在水溶液中未显示任何底物结合。这些系统不能作为受体起作用主要是由于对重要的环烷芳族环-客体相互作用的空间位阻。同样，腔内功能性的有利溶剂化可以防止复合物的形成。发现由新型间隔基和二苯甲烷单元构建的杂合受体可以结合平坦的芳香族底物以及庞大的[4

  DOI：

  10.1002/hlca.19940770320
• 作为产物：
  描述：

  1-甲氧基-4-(2-硝基乙基)苯 在 potassium fluoride 、 盐酸二甲胺 、 铁粉 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 文拉法辛杂质4
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

  摘要：

  Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containing a classic nitrostyrene structure are shown to have antiproliferative activities in vitro in a range of malignant cell lines, particularly against Burkitt's lymphoma derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.054

文献信息

• Synthesis of (E)- and (Z)-pulvinones
  作者：Alexander C. Campbell、Maurice S. Maidment、John H. Pick、Donald F. M. Stevenson

  DOI：10.1039/p19850001567

  日期：——

  one of which involves a novel Wittig reaction. For the first time, members of the E-series, including the parent (E)-pulvinone, are reported and the structural elucidation of the geometric isomers is described. A method for quantitatively converting (E)-pulvinones into (Z)-pulvinones is presented, together with a technique for differentiating between the isomers.

  已经开发出两种新的途径获得pulvinones，其中一种涉及新颖的Wittig反应。首次报道了E系列的成员，包括母体（E）-普尔维酮，并描述了几何异构体的结构。提出了一种将（E）-普尔维酮定量转化为（Z）-普尔维酮的方法，以及区分异构体的技术。
• Catalytic Asymmetric (3 + 3) Cycloaddition of Oxyallyl Zwitterions with α-Diazomethylphosphonates
  作者：Yan Liu、Xian Peng、Rui She、Xin Zhou、Yungui Peng

  DOI：10.1021/acs.orglett.1c02809

  日期：2021.9.17

  The unique structure of oxyallyls represents a significant challenge for their catalytic asymmetric applications. Herein, an unprecedented chiral imidodiphosphoric acid-catalytic enantioselective (3 + 3) cycloaddition between oxyallyl zwitterions generated in situ from α-haloketones and α-diazomethylphosphonates was developed. Pharmaceutically interesting chiral pyridazine-4(1H)-ones were obtained

  氧烯丙基的独特结构对其催化不对称应用提出了重大挑战。在此，开发了一种前所未有的手性亚氨基二磷酸催化的对映选择性（3 + 3）环加成反应，在由 α-卤代酮和 α-重氮甲基膦酸酯原位生成的氧烯丙基两性离子之间进行了环加成反应。药学上令人感兴趣的手性哒嗪-4( 1H )-酮以高达 98% 的收率获得，具有出色的立体选择性（高达 99% ee，> 99:1 dr）。
• Palladium-Catalyzed Enantioselective C–H Aminocarbonylation: Synthesis of Chiral Isoquinolinones
  作者：Hui Han、Tao Zhang、Shang-Dong Yang、Yu Lan、Ji-Bao Xia

  DOI：10.1021/acs.orglett.9b00315

  日期：2019.3.15

  A Pd-catalyzed enantioselective C–H carbonylation by desymmetrization was developed with commercially available L-pyroglutamic acid as chiral ligand. Isoquinolinones were successfully obtained with good yields and high enantioselectivities. Mechanistic studies and DFT calculations provided a reasonable reaction pathway.

  利用可商购的L-焦谷氨酸作为手性配体，开发了一种Pd催化的非对称化CH羰基化对映体。异喹啉酮以高收率和高对映选择性成功获得。机理研究和DFT计算提供了合理的反应途径。
• Efficient Synthesis of Substituted Polyarylphthalimides via Cycloaddition of Cyclopentadienones with 2-Bromomaleimide
  作者：Jacques Einhorn、Rémi Vanel、Florian Berthiol、Bernard Bessières、Cathy Einhorn

  DOI：10.1055/s-0030-1260556

  日期：2011.6

  Functionalized tetraarylphthalimides or diarylphthal­imides fused with an acenaphthene moiety have been prepared in one step from 2-bromomaleimide and tetraarylcyclopentadienones (tetracyclones) or 7,9-diaryl-8H-cyclopentacenaphthylene-8-ones (acecyclones). The reaction, involving a cycloaddition-decarbonylation-dehydrobromination sequence, gives high isolated yields and is compatible with the presence of various functional groups.

  已通过一步法合成了带有acenaphthene结构的功能化四芳基邻苯二甲酰亚胺或二芳基邻苯二甲酰亚胺。利用2-溴马来酰亚胺与四芳基环戊二烯酮（四环酮）或7,9-二芳基-8H-环戊并苊-8-酮（苊环酮）反应制得。该反应涉及环加成-脱羰基-脱溴化氢序列，具有高纯度产率，且能兼容多种官能团的存在。
• Organocatalyzed oxidative N-annulation for diverse and polyfunctionalized pyridines
  作者：Hari Datta Khanal、Yong Rok Lee

  DOI：10.1039/c5cc01807b

  日期：——

  A variety of polyfunctionalized pyridines were synthesized from readily available ketones with α,β-unsaturated aldehydes and ammonium acetate under a mild organocatalyst.

  通过使用易于获得的酮与α,β-不饱和醛和醋酸铵，在温和的有机催化剂下，合成了多种多官能团化的吡啶。