2-fluoro-(3α-R)-(+)-sclareolide | 1402142-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2-fluoro-(3α-R)-(+)-sclareolide
• 英文别名: (3aR,5aS,9aS,9bR)-8-fluoro-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(3aH)-one；2α-fluorosclareolide；(3aR,5aS,8S,9aS,9bR)-8-fluoro-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one；(3aR,5aS,8S,9aS,9bR)-8-fluorodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one；(3aR,8S,9aS,9bR)-8-fluoro-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one；(2S)-2-fluorosclareolide；(3aR,5aS,8S,9aS,9bR)-8-fluoro-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one
• CAS: 1402142-82-8
• 化学式: C₁₆H₂₅FO₂
• 分子量: 268.372
• InChiKey: JBUMAEITAFJOJI-RWNPNPFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  香紫苏内酯 在 N-(tert-Butyl)-N-((1-phenylvinyl)oxy)-3,5-bis(trifluoromethyl)benzamide 、 N-氟代双苯磺酰胺 作用下， 以74%的产率得到2-fluoro-(3α-R)-(+)-sclareolide
  参考文献：
  名称：

  [EN] REAGENTS AND METHODS FOR ALIPHATIC CARBON—HYDROGEN BOND FUNCTIONALIZATION
  [FR] RÉACTIFS ET PROCÉDÉS DE FONCTIONNALISATION DE LIAISON CARBONE-HYDROGÈNE ALIPHATIQUE

  摘要：

  The subject matter contained herein relates generally to methods and compounds that facilitate aliphatic carbon-hydrogen bond functionalization by group transfer via a nitrogen-centered radical in the presence of a trap, and the functionalized compounds prepared therefrom. The subject matter described herein provides a platform and the ability to efficiently and selectively introduce a range of valuable functionality on diverse hydrocarbon substrates ranging from methane to polyolefins with >3500 carbon atoms. As described herein, the reagents employed can form reactive N-centered radicals, the kinetics of which do not compete with companion radical traps. This technology finds usefulness in enhancing capabilities in late-stage diversification, while the molecules and materials now made accessible can provide solutions to important challenges in medicinal chemistry and materials science.

  公开号：

  WO2022241129A1

文献信息

• Electrochemical C(sp3)–H Fluorination
  作者：Yusuke Takahira、Miao Chen、Yu Kawamata、Pavel Mykhailiuk、Hugh Nakamura、Byron K. Peters、Solomon H. Reisberg、Chao Li、Longrui Chen、Tamaki Hoshikawa、Tomoyuki Shibuguchi、Phil S. Baran

  DOI：10.1055/s-0037-1611737

  日期：2019.6

  A simple and robust method for electrochemical alkyl C–H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C–H bonds are converted into their C–F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.

  提出了一种简单而可靠的电化学烷基 C-H 氟化方法。使用简单的硝酸盐添加剂、广泛使用的氟源 (Selectfluor) 和碳基电极，各种活化和未活化的 C-H 键被转化为它们的 C-F 同系物。100 克氟缬氨酸制剂也证明了反应的可扩展性。
• Visible light-promoted metal-free sp³-C–H fluorination
  作者：Ji-Bao Xia、Chen Zhu、Chuo Chen

  DOI：10.1039/c4cc05650g

  日期：——

  Photoexcited acetophenone can catalyze the fluorination of unactivated C(sp(3))-H groups. While acetophenone, a colorless oil, only has a trace amount of absorption in the visible light region, its photoexcitation can be achieved by irradiation with light generated by a household compact fluorescent lamp (CFL). This operational simple method provides improved substrate scope for the direct incorporation

  光激发苯乙酮可以催化未活化的 C(sp(3))-H 基团的氟化。虽然苯乙酮是一种无色油，在可见光区域只有微量的吸收，但它的光激发可以通过用家用紧凑型荧光灯 (CFL) 产生的光照射来实现。这种操作简单的方法为将氟原子直接结合到简单的有机分子中提供了改进的底物范围。CFL 照射还可用于促进无色单芳基酮和烯酮/烯醛的某些经典的紫外线促进光反应。
• A Convenient Photocatalytic Fluorination of Unactivated CH Bonds
  作者：Shira D. Halperin、Hope Fan、Stanley Chang、Rainer E. Martin、Robert Britton

  DOI：10.1002/anie.201400420

  日期：2014.4.25

  providing a means to block site‐selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the

  氟化反应是现代药物化学必不可少的，因此提供了一种手段来阻止药物的定点代谢降解，并为正电子发射断层扫描成像提供放射性示踪剂的访问。尽管目前在氟化试剂和方法中已经很复杂，但是未活化的CH键的氟化仍然是一个巨大的挑战。本文报道的为未活化的C直接氟化的便利和经济的方法可以利用该夺氢一decatungstate光催化剂的能力结合温和的氟原子转移试剂H键Ñ-氟苯磺酰亚胺。这种操作简单的反应可直接进入各种氟化有机分子，包括结构复杂的天然产物，酰基氟和氟化氨基酸衍生物。
• Selective fluorination of alkyl C–H bonds <i>via</i> photocatalysis
  作者：Choon Wee Kee、Kek Foo Chin、Ming Wah Wong、Choon-Hong Tan

  DOI：10.1039/c4cc01848f

  日期：——

  We report the generation of cationic N-radicals from Selectfluor® via energy transfer with anthraquinone as a photocatalyst for the fluorination of unactivated C–H bonds.

  我们报道了使用蒽醌作为光催化剂，通过与Selectfluor®进行能量转移，生成阳离子N-自由基，用于氟化未活化的C-H键。
• Mechanochemical Direct Fluorination of Unactivated C( <i>sp</i> ³ )−H Bonds
  作者：Sehye Min、Beomsoon Park、Jantakan Nedsaengtip、Soon Hyeok Hong

  DOI：10.1002/adsc.202200206

  日期：2022.6.21

  The mechanochemical fluorination of unactivated C(sp3)−H bonds has been achieved using N-fluorobenzenesulfonimide as both a precursor of the hydrogen-atom-transfer reagent and a bench-stable fluorine source. The control experiments revealed that mechanical energy is essential for realizing this reaction.

  使用N-氟苯磺酰亚胺作为氢原子转移试剂的前体和稳定的氟源，实现了未活化的 C( sp 3 )-H 键的机械化学氟化。对照实验表明，机械能对于实现这一反应至关重要。