methyl 2-fluoro-1-tetralone-2-carboxylate | 163978-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-fluoro-1-tetralone-2-carboxylate
• 英文别名: methyl 2-fluoro-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate；Methyl 2-fluoro-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• CAS: 163978-58-3
• 化学式: C₁₂H₁₁FO₃
• 分子量: 222.216
• InChiKey: PPSMQFKPEHAPBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-fluoro-1-tetralone-2-carboxylate 在 盐酸 、 R(+)-alpha-甲基苄胺 、 四氯化钛 作用下， 生成 methyl 2R-fluoro-1-tetralone-2-carboxylate 、 methyl 2S-fluoro-1-tetralone-2-carboxylate
  参考文献：
  名称：

  Epoxidation with dioxiranes derived from 2-fluoro-2-substituted-1-tetralones and -1-indanones

  摘要：

  Homochiral 2-fluoro-2-substituted-1-tetralones (10a, 10b, 13) and ethyl 2-fluoro-1-indanone-2-carboxylate (16) have been isolated. The dioxirane derivatives of these ketones have been prepared in situ, and have been shown to epoxidise alkenes but not enantioselectively. The dioxirane derivative of methyl 2,5,7-trifluoro-1-indanone-2-carboxylate (18) has been shown to be comparatively efficient in epoxidation.

  DOI：

  10.1016/0040-4020(95)00075-j
• 作为产物：
  描述：

  1,2,3,4-四氢-1-氧代-2-萘羧酸甲酯 在 N-fluorobis(methanesulfonyl)imide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以91%的产率得到methyl 2-fluoro-1-tetralone-2-carboxylate
  参考文献：
  名称：

  Methyl NFSI: atom-economical alternative to NFSI shows higher fluorination reactivity under Lewis acid-catalysis and non-catalysis

  摘要：

  Me-NFSI对于活性甲基的氟化在Lewis酸催化和非催化条件下比NFSI更有效。

  DOI：

  10.1039/c5gc02612a

文献信息

• Methyl NFSI: atom-economical alternative to NFSI shows higher fluorination reactivity under Lewis acid-catalysis and non-catalysis
  作者：Kazunobu Fukushi、Satoru Suzuki、Tomohiro Kamo、Etsuko Tokunaga、Yuji Sumii、Takumi Kagawa、Kosuke Kawada、Norio Shibata

  DOI：10.1039/c5gc02612a

  日期：——

  Me-NFSI is more effective for the fluorination of active methines under Lewis acid-catalysis and non-catalysis than NFSI.

  Me-NFSI对于活性甲基的氟化在Lewis酸催化和非催化条件下比NFSI更有效。
• Chiral<i>N</i>-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination
  作者：Chuan-Le Zhu、Mayaka Maeno、Fa-Guang Zhang、Taiki Shigehiro、Takumi Kagawa、Kosuke Kawada、Norio Shibata、Jun-An Ma、Dominique Cahard

  DOI：10.1002/ejoc.201300956

  日期：2013.10

  design, synthesis, and application of de novo chiral fluorinating agents as analogues of popular N-fluorodibenzenesulfonimide (NFSI). The fluorination step by means of elemental fluorine is presented. Enantioselective fluorination is demonstrated in cyclic β-keto esters and in the synthesis of BMS-204352 (up to 86 % ee). Oxidative aminofluorination is also examined.

  这项工作描述了作为流行的 N-氟二苯磺酰亚胺 (NFSI) 类似物的从头手性氟化剂的设计、合成和应用。介绍了通过元素氟的氟化步骤。在环状 β-酮酯和 BMS-204352（高达 86% ee）的合成中证明了对映选择性氟化。还检查了氧化氨基氟化。
• N-Fluoro-3-ethyl-3-methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[e]1,2-thiazin-4-one, a new and efficient agent for electrophilic fluorination of carbanions
  作者：Yoshio Takeuchi、Zhaopeng Liu、Emiko Suzuki、Norio Shibata、Kenneth L Kirk

  DOI：10.1016/s0022-1139(99)00028-7

  日期：1999.7

  N-Fluoro-3-ethyl-3-methyl-1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-benzo[e]1,2-thiazin-4-one (1) was prepared in good yield by fluorination of the corresponding sultam (3) with FClO3. The sultam (3) was prepared from saccharin (2) in 3 steps. The N-fluorosultam (1), a very stable crystalline solid, was found to fluorinate carbanions readily in good to excellent yields. (C) 1999 Elsevier Science S.A. All rights reserved.
• Epoxidation with dioxiranes derived from 2-fluoro-2-substituted-1-tetralones and -1-indanones
  作者：David S. Brown、Brian A. Marples、Paul Smith、Lesley Walton

  DOI：10.1016/0040-4020(95)00075-j

  日期：1995.3

  Homochiral 2-fluoro-2-substituted-1-tetralones (10a, 10b, 13) and ethyl 2-fluoro-1-indanone-2-carboxylate (16) have been isolated. The dioxirane derivatives of these ketones have been prepared in situ, and have been shown to epoxidise alkenes but not enantioselectively. The dioxirane derivative of methyl 2,5,7-trifluoro-1-indanone-2-carboxylate (18) has been shown to be comparatively efficient in epoxidation.
• Self‐Sustaining Fluorination of Active Methylene Compounds and High‐Yielding Fluorination of Highly Basic Aryl and Alkenyl Lithium Species with a Sterically Hindered <i>N</i> ‐Fluorosulfonamide Reagent
  作者：Yuhao Yang、Gerald B. Hammond、Teruo Umemoto

  DOI：10.1002/anie.202211688

  日期：2022.10.24

  By developing a sterically hindered fluorinating agent, N-fluoro-N-(tert-butyl)-tert-butanesulfonamide (NFBB), we discovered a conceptually novel base-catalyzed, self-sustaining fluorination of active methylene compounds and achieved an unprecedented high-yield fluorination of highly basic (hetero)aryl and alkenyl lithium species.

  通过开发空间位阻氟化剂N-氟-N- (叔丁基)-叔丁磺酰胺(NFBB)，我们发现了一种概念性新颖的碱催化、活性亚甲基化合物自持氟化反应，并实现了前所未有的高产率。产生高碱性（杂）芳基和烯基锂物种的氟化。