Z-(2-chloro-2-nitroethenyl)-2-fluorobenzene | 187585-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z-(2-chloro-2-nitroethenyl)-2-fluorobenzene
• 英文别名: 1-[(Z)-2-chloro-2-nitroethenyl]-2-fluorobenzene
• CAS: 187585-23-5
• 化学式: C₈H₅ClFNO₂
• 分子量: 201.585
• InChiKey: ANIRMVIVXDZCPC-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-(2-chloro-2-nitroethenyl)-2-fluorobenzene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 2-(2-Fluoro-phenyl)-3-nitro-chromen-4-one
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones

  摘要：

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.

  DOI：

  10.1016/s0223-5234(97)84363-2
• 作为产物：
  描述：

  溴代硝基甲烷 、 2-氟苯甲醛 在 potassium fluoride 、 盐酸二甲胺 作用下， 以 xylene 为溶剂， 反应 3.0h， 以74%的产率得到Z-(2-chloro-2-nitroethenyl)-2-fluorobenzene
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones

  摘要：

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.

  DOI：

  10.1016/s0223-5234(97)84363-2

文献信息

• Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes
  作者：Damien Bonne、Jean Rodriguez、Diana Becerra、Wilfried Raimondi、Daniel Dauzonne、Thierry Constantieux

  DOI：10.1055/s-0035-1562446

  日期：——

  leading to the title products as single diastereomers with enantiomeric excesses from 86% up to 97%. Alkyl 4,5-dihydrofuran-2-carboxylates can be efficiently obtained via an enantioselective organocatalyzed consecutive reaction between α-keto esters and (Z)-(2-chloro-2-nitroethenyl)benzenes. The overall sequence combines a (R,R)-TUC-catalyzed Michael addition with a DABCO-promoted intramolecular O-alkylation

  献给教授迪特尔·恩德斯在他70之际个生日 抽象的 通过α-酮酸酯和（Z）-（2-氯-2-硝基乙烯基）苯之间的对映选择性有机催化连续反应，可以有效地获得4，5-二氢呋喃-2-羧酸烷基酯。整个序列结合了（R，R）-TUC催化的迈克尔加成与DABCO促进的分子内O-烷基化，得到标题产物，为单一非对映异构体，对映体过量从86％到97％。 通过α-酮酸酯和（Z）-（2-氯-2-硝基乙烯基）苯之间的对映选择性有机催化连续反应，可以有效地获得4，5-二氢呋喃-2-羧酸烷基酯。整个序列结合了（R，R）-TUC催化的迈克尔加成与DABCO促进的分子内O-烷基化，得到标题产物，为单一非对映异构体，对映体过量从86％到97％。
• Synthesis and Biological Evaluation of 5-Arylfuro(2,3-d)pyrimidines as Novel Dihydrofolate Reductase Inhibitors.
  作者：Farid WAHID、Claude MONNERET、Daniel DAUZONNE

  DOI：10.1248/cpb.47.156

  日期：——

  A series of about fifty novel 5-arylfuro[2,3-d]pyrimidine derivatives were synthesized as potential inhibitors of dihydrofolate reductase (DHFR) arising from different species. Weak enzyme inhibition was observed for most of the compounds, with only a few reaching IC50 values less than 30 microM. With regards to antibacterial and anti-malarial potency, only seven compounds showed a modest in vitro

  合成了一系列约五十种新颖的5-芳基呋喃[2,3-d]嘧啶衍生物，作为潜在的抑制剂，其来自不同物种的二氢叶酸还原酶（DHFR）。对于大多数化合物，酶抑制作用较弱，只有少数达到的IC50值小于30 microM。关于抗菌和抗疟疾效力，只有七种化合物显示出对某些细菌菌株的适度体外活性，只有三种产物证明对恶性疟原虫具有显着活性。
• Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones
  作者：D Dauzonne、B Folléas、L Martinez、GG Chabot

  DOI：10.1016/s0223-5234(97)84363-2

  日期：1997.1

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.