5'-methoxy-4-nitro-2,2',5-trifluorobenzophenone | 1015414-82-0

• 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: 5'-methoxy-4-nitro-2,2',5-trifluorobenzophenone
• 英文别名: (2,5-Difluoro-4-nitrophenyl)(2-fluoro-5-methoxyphenyl)methanone；(2,5-difluoro-4-nitrophenyl)-(2-fluoro-5-methoxyphenyl)methanone
• CAS: 1015414-82-0
• 化学式: C₁₄H₈F₃NO₄
• 分子量: 311.217
• InChiKey: NONWQODYOBEAGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-methoxy-4-nitro-2,2',5-trifluorobenzophenone 在 水 、 氢溴酸 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苯甲醛肟 、 copper dichloride 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 、 mineral oil 为溶剂， 反应 180.0h， 生成 6-(5-benzyloxy-2-fluorobenzoyl)-2,2-dimethyl-5-fluoro-8-methoxychromene
  参考文献：
  名称：

  Xanthone Natural Products via N-Heterocyclic Carbene Catalysis: Total Synthesis of Atroviridin

  摘要：

  The total synthesis of atroviridin has been accomplished by a linear route involving the N-heterocyclic carbene (NHC)-catalyzed aroylation of the fluorobenzene derivative, Claisen cyclization of the O-propargylated benzo-phenones, and intramolecular 1,4-addition of the quinone intermediates. The result provides a viable route to xanthone natural products.

  DOI：

  10.1021/jo200303c
• 作为产物：
  描述：

  2,4,5-三氟硝基苯 、 2-氟-5-甲氧基苯甲醛 在 sodium hydride 、 1,3-二甲基咪唑 碘 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.17h， 以76%的产率得到5'-methoxy-4-nitro-2,2',5-trifluorobenzophenone
  参考文献：
  名称：

  通过有机催化和区域选择性克莱森重排完全合成TermicalcicolanoneA。

  摘要：

  已经开发了利用多个亲核性芳族取代和周环反应的抗癌黄酮天然产物termicalcicolanone A的全合成。吡喃并[3,2 - b ]黄嘌呤-6-骨架是通过NHC催化的芳基化反应生成的二苯甲酮中间体，经克莱森环化形成吡喃环，并通过分子内的1,4-加成反应构建an吨酮骨架。通过区域选择性克莱森重排在合成的最后阶段引入异戊二烯基。合成已通过19个步骤完成。

  DOI：

  10.1021/acs.orglett.9b00731

文献信息

• Total Synthesis of Termicalcicolanone A via Organocatalysis and Regioselective Claisen Rearrangement
  作者：Saki Ito、Taiki Kitamura、Sundaram Arulmozhiraja、Kei Manabe、Hiroaki Tokiwa、Yumiko Suzuki

  DOI：10.1021/acs.orglett.9b00731

  日期：2019.4.19

  A total synthesis of an anticancer xanthone natural product termicalcicolanone A utilizing multiple nucleophilic aromatic substitutions and pericyclic reactions has been developed. The pyrano[3,2-b]xanthen-6-one scaffold was constructed via NHC-catalyzed aroylation to produce the benzophenone intermediate, Claisen cyclization to form the pyran ring, and intramolecular 1,4-addition to construct the

  已经开发了利用多个亲核性芳族取代和周环反应的抗癌黄酮天然产物termicalcicolanone A的全合成。吡喃并[3,2 - b ]黄嘌呤-6-骨架是通过NHC催化的芳基化反应生成的二苯甲酮中间体，经克莱森环化形成吡喃环，并通过分子内的1,4-加成反应构建an吨酮骨架。通过区域选择性克莱森重排在合成的最后阶段引入异戊二烯基。合成已通过19个步骤完成。
• N-Heterocyclic Carbene-Catalyzed Nucleophilic Aroylation of Fluorobenzenes
  作者：Yumiko Suzuki、Shinya Ota、Yoshinori Fukuta、Yuki Ueda、Masayuki Sato

  DOI：10.1021/jo7023569

  日期：2008.3.1

  In N-heterocyclic carbene (NHCs) catalyzed nucleophilic substitution of fluorobenzenes, fluoro groups are replaced by aroyl groups, which are derived from aromatic aldehydes. 1,3,4,5-Tetramethylimidazol-2-ylidene is found to be an efficient catalyst. The catalyst loading can be reduced to I mol % without a significant decrease in the product yields. Polysubstituted benzophenones are synthesized from fluorobenzenes and benzaldehydes by the NHC-catalyzed aroylation.
• Recyclable polyetheretherketone fiber-supported N-heterocyclic carbene catalysts for nucleophilic acylation of fluorobenzenes
  作者：Xian-Lei Shi、Benyu Sun、Qianqian Hu、Kun Liu、Pengyu Li、Juanjuan Wang

  DOI：10.1039/d0cc04394j

  日期：——

  We report for the first time a novel support of polyetheretherketone fiber for the synthesis of recyclable N-heterocyclic carbene (NHC) catalysts. The fiber catalysts were verified in nucleophilic acylation of fluorobenzenes with superior catalytic activities, and successfully recycled by a tiny pair of tweezers over 21 cycles with minimal loss of performance.

  我们首次报告了聚醚醚酮纤维对可循环使用的N-杂环卡宾（NHC）催化剂合成的新型支持。纤维催化剂在氟苯的亲核酰化反应中得到了验证，具有优异的催化活性，并通过一对镊子在21个循环内成功回收了该催化剂，而性能损失最小。
• Xanthone Natural Products via <i>N</i>-Heterocyclic Carbene Catalysis: Total Synthesis of Atroviridin
  作者：Yumiko Suzuki、Yoshinori Fukuta、Shinya Ota、Masayo Kamiya、Masayuki Sato

  DOI：10.1021/jo200303c

  日期：2011.5.20

  The total synthesis of atroviridin has been accomplished by a linear route involving the N-heterocyclic carbene (NHC)-catalyzed aroylation of the fluorobenzene derivative, Claisen cyclization of the O-propargylated benzo-phenones, and intramolecular 1,4-addition of the quinone intermediates. The result provides a viable route to xanthone natural products.