(R)-methyl 5-chloro-2-fluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate | 1360817-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-methyl 5-chloro-2-fluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: methyl (R)-5-chloro-2-fluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate；methyl (2R)-6-chloro-2-fluoro-3-oxo-1H-indene-2-carboxylate
• CAS: 1360817-56-6
• 化学式: C₁₁H₈ClFO₃
• 分子量: 242.634
• InChiKey: DXTVCJNDOGHRPA-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯-1-氧代-2,3-二氢-1H-茚-2-羧酸甲酯 在 copper(II) bis(trifluoromethanesulfonate) 、 N-氟代双苯磺酰胺 、 bis-[2-((4S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-amine 作用下， 以 neat (no solvent) 为溶剂， 反应 0.07h， 以99%的产率得到(R)-methyl 5-chloro-2-fluoro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  在球磨机中由手性铜配合物催化的快速，无溶剂和高对映选择性氟化的小β-酮酯

  摘要：

  使用行星式球磨机已经开发了在无溶剂条件下由二苯胺连接的双（恶唑啉）-Cu（OTf）2络合物催化的快速和高度对映选择性氟化的小β-酮酸酯。

  DOI：

  10.1039/c6gc03306g

文献信息

• Enantioselective Fluorination of β-Ketoesters Catalyzed by Chiral Sodium Phosphate: Remarkable Enhancement of Reactivity by Simultaneous Utilization of Metal Enolate and Metal Phosphate
  作者：Keiji Mori、Ayaka Miyake、Takahiko Akiyama

  DOI：10.1246/cl.130934

  日期：2014.1.5

  A highly enantioselective fluorination of β-ketoesters catalyzed by chiral sodium phosphate is achieved. In this process, the simultaneous formation of sodium enolate and sodium phosphate under basic conditions is the key to achieving excellent selectivity. Indanone derivatives as well as benzofuranone derivatives could be employed in this reaction to afford the fluorinated adducts in good yields with good to excellent enantioselectivities.

  在手性磷酸钠催化下，实现了 β 酮酯的高对映选择性氟化。在此过程中，在碱性条件下同时形成烯醇钠和磷酸钠是获得优异选择性的关键。茚酮衍生物和苯并呋喃酮衍生物均可用于该反应，从而以良好的产率和出色的对映选择性获得氟化加合物。
• Cu(I)-catalyzed asymmetric chlorination of β-keto esters in the presence of chiral phosphine-schiff base type ligands
  作者：Jia-Jun Jiang、Jian Huang、De Wang、Zhi-Liang Yuan、Mei-Xin Zhao、Fei-Jun Wang、Min Shi

  DOI：10.1002/chir.20913

  日期：2011.3

  Chiral phosphine‐Schiff base type ligand L8 prepared from (R)‐(−)‐2‐(diphenylphosphino)‐1,1'‐binaphthyl‐2'‐amine was found to be a fairly effective ligand for Cu(I)‐promoted enantioselective chlorination of β‐keto esters to give the corresponding products in high yields and with moderate enantioselectivities. Chirality 2011. © 2010 Wiley‐Liss, Inc.

  由（R）-（-）-2-（二苯基膦基）-1,1'-联萘-2-'胺制备的手性膦Schiff碱型配体L8被发现是Cu（I）促进的相当有效的配体β-酮酯的对映选择性氯化，以高收率和中等对映选择性得到相应的产物。手性2011。©2010 Wiley-Liss，Inc.。
• Novel Tartrate-Based Guanidines for Enantioselective Fluorination of 1,3-Dicarbonyl and α-Cyano Carbonyl Compounds
  作者：Liwei Zou、Xiaoze Bao、Huanrui Zhang、Yuming Song、Jingping Qu、Baomin Wang

  DOI：10.1071/ch14179

  日期：——

  electronic properties. A guanidine molecule of this library with an incorporated 2,6-diisoaniline fragment was identified as a suitable promoter for the enantioselective fluorination of 1,3-dicarbonyl and α-cyano carbonyl compounds to furnish the fluorinated product with up to 84 % ee and 99 % yield using N-fluorobenzenesulfonimide (NFSI) as the fluorinating agent.

  具有酒石酸骨架的新型手性胍库具有可调节的空间和电子特性，可轻松访问。该文库中掺入2，6-二异苯胺片段的胍分子被鉴定为1,3-二羰基和α-氰基羰基化合物的对映选择性氟化的合适促进剂，可为氟化产物提供84％ee和99使用N-氟苯磺酰亚胺（NFSI）作为氟化剂的收率（％）。
• Cyclic Dinucleotide-Based Enantioselective Fluorination in Water
  作者：Xingchen Dong、Shuting Lv、Qianqian Qi、Youkun Gu、Peizhe Wu、Wenyue Zhang、Zhuolin Zhang、Libing Yang、Jiaqi Li、Yashao Chen、Changhao Wang

  DOI：10.1021/acs.joc.2c02116

  日期：2023.1.6

  structures of DNA serve as potent chiral scaffolds for DNA-based asymmetric catalysis, yet in most cases tens to hundreds of nucleotides in DNA hybrid catalysts hinder the deep insight into their structure–activity relationship. Owing to the structural simplicity and design flexibility of nucleotides, nucleotide-based catalysts have been emerging as a promising way to obtain fine structural information

  DNA 的不同结构可作为基于 DNA 的不对称催化的有效手性支架，但在大多数情况下，DNA 杂化催化剂中的数十至数百个核苷酸阻碍了对其结构-活性关系的深入了解。由于核苷酸的结构简单性和设计灵活性，基于核苷酸的催化剂已成为获得精细结构信息和理解催化机制的有前途的方法。在此，我们发现环状双 AMP (c-di-AMP) 和 1,10-菲咯啉硝酸铜 (II) (Cu(phen)(NO 3 ) 2 ) 的环状二核苷酸组装成 c-di- AMP 基催化剂 (c-di-AMP/Cu(phen)(NO 3 ) 2)，它可以在水中快速实现对映选择性氟化，产率为 90-99%，对映体过量 (ee) 高达 90%。c-di-AMP 和 Cu(phen)(NO 3 ) 2之间的主客体相互作用主要以超分子相互作用模式提出，紫外-可见、荧光、圆二色性和核磁共振的光谱技术证明了这一点。Cu(phen)(NO 3 )
• Enantioselective fluorination of β-ketoesters catalysed by complexes of new mono-oxazoline ligands
  作者：Teng Niu、Xiping Han、Danfeng Huang、Ke-Hu Wang、Yingpeng Su、Yulai Hu、Ying Fu

  DOI：10.1016/j.jfluchem.2015.02.017

  日期：2015.7

  A new kind of mono-oxazoline ligands which combined diaryl methyl units and chiral oxazoline units together using pyridine as linker was prepared. Their applications in enantioselective electrophilic fluorination of beta-ketoesters by NFSI were investigated, and the corresponding products were obtained in excellent yield (up to 90%) and good enantioselectivity (78%) in CH2Cl2 at -60 degrees C. (C) 2015 Elsevier B.V. All rights reserved.