tert-butyl 2,6-difluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate | 1617519-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: tert-butyl 2,6-difluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: tert-butyl (2S)-2,5-difluoro-3-oxo-1H-indene-2-carboxylate
• CAS: 1617519-17-1
• 化学式: C₁₄H₁₄F₂O₃
• 分子量: 268.26
• InChiKey: ULRCVZJSDNQLRJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 6-fluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 在 C₃₀H₄₀Br₂ClFeN₂O₂ 、 silver perchlorate 、 N-氟代双苯磺酰胺 作用下， 以 乙腈 为溶剂， 以95%的产率得到tert-butyl 2,6-difluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  Iron(iii)–salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles

  摘要：

  手性铁(III)–salan复合物催化了β-酮酯和N-Boc氧杂环戊烯的高度对映选择性α-氟化和α-羟基化反应，在温和的反应条件下获得相应产物，产率高，对映体过量值良好至优异。

  DOI：

  10.1039/c4cc01631a

文献信息

• Catalytic Asymmetric Fluorination of Alkyl 1-indanone-2-carboxylates Ruled by Pybox-Eu(III) Combination
  作者：Albert Granados、Pau Sarró、Adelina Vallribera

  DOI：10.3390/molecules24061141

  日期：——

  A highly enantioselective catalytic method for the synthesis of quaternary α-fluoro derivatives of 3-oxo esters is described. The reaction uses europium (III) triflate and commercially available chiral pybox-type C2-symmetric ligand. Excellent results in terms of yields and enantioselectivities were assured using the electrophilic NFSI reagent under mild reaction conditions.

  描述了一种用于合成 3-氧代酯的季α-氟衍生物的高对映选择性催化方法。该反应使用三氟甲磺酸铕 (III) 和市售的手性 pybox 型 C2 对称配体。在温和的反应条件下使用亲电 NFSI 试剂确保了产率和对映选择性方面的优异结果。
• Development of Planar Chiral Iodoarenes Based on [2.2]Paracyclophane and Their Application in Catalytic Enantioselective Fluorination of β-Ketoesters
  作者：Yang Wang、Hang Yuan、Hongfei Lu、Wen-Hua Zheng

  DOI：10.1021/acs.orglett.8b00711

  日期：2018.5.4

  The design and synthesis of novel planar chiral iodoarenes based on [2.2]paracyclophane is reported. A process of highly enantioselective oxidative fluorination of a β-ketoester with 3HF–Et3N as a nucleophilic fluoride source mediated by these new hypervalent iodine catalysts has been developed. This represents the first highly enantioselective reaction catalyzed by planar chiral hypervalent iodine

  报道了基于[2.2]对环环烷的新型平面手性碘代芳烃的设计与合成。已经开发了由这些新的高价碘催化剂介导的以3HF-Et 3 N作为亲核氟化物源的β-酮酸酯的高对映选择性氧化氟化的方法。这代表了由平面手性高价碘催化的第一个高度对映选择性反应。
• A New Class of Squaramide-Containing Phase-Transfer Catalysts: Application to Asymmetric Fluorination of β-Keto Esters
  作者：Yingjie Lin、Haifeng Duan、Bin Wang、Yingdong He、Xuancheng Fu、Zhonglin Wei

  DOI：10.1055/s-0035-1560645

  日期：——

  The squaramide moiety has proven to be a powerful hydrogen-bonding donor in organocatalysis, but chiral phase-transfer catalysts bearing the squaramide motif have not been reported so far. Reported herein is this kind of catalyst and their catalytic performance in the asymmetric fluorination of beta-keto esters.