2-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one | 122795-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 2-Fluoro-2-methyl-1-tetralone；2-fluoro-2-methyl-3,4-dihydronaphthalen-1-one
• CAS: 122795-15-7
• 化学式: C₁₁H₁₁FO
• 分子量: 178.206
• InChiKey: KUHPHKLCWLRLRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 仲丁醇 为溶剂， 反应 2.75h， 生成 (S)-2-fluoro-2-methyl-1-tetralone
  参考文献：
  名称：

  Asymmetric Fluorination of Enolates with Nonracemic N-Fluoro-2,10-Camphorsultams

  摘要：

  The asymmetric "electrophilic" fluorination of tertiary enolates by nonracemic N-fluoro-2,10-camphorsultams 3 affords quaternary alpha-fluoro carbonyl compounds in modest yield and ee. The highest asymmetric induction was observed for the fluorination of the sodium enolate of 2-methyl-1-tetralone (8a) by (-)-N-fluoro-2,10-(3,3-dichlorocamphorsultam) (3b) to give (S)-(+)-2-fluoro-2-methyl-1-tetralone (9a) in 70% ee. The absolute configuration was established by X-ray crystallography of the corresponding diastereomeric beta-hydroxy sulfoximine prepared from (+/-)-9a and the Johnson reagent. The asymmetric induction exhibited by 3 is opposite to that of the closely related enolate hydroxylation reagents nonracemic (camphorylsulfonyl)oxaziridines 4. The N-fluoro sultams 3 were prepared by fluorination (10% F-2/N-2) of the corresponding sultams 5.

  DOI：

  10.1021/jo972045x
• 作为产物：
  描述：

  trimethyl(2-methyl-3,4-dihydronaphthalen-1-yloxy)silane 在 1-benzyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditriflate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以98%的产率得到2-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  [18F] Selectfluor bis（triflate）的放射合成与评估

  摘要：

  Selectfluor是反应性最强，最常用的亲电氟化N-F试剂之一，已经用18 F进行了放射性标记。所得的[ 18 F]标记的新型N-F试剂安全，无毒且易于处理。[ 18 F] Selectfluor bis（triflate）和AgOTf的组合使用可通过在室温下通过简单的“摇动和混合”方案制备富电子的18 F-芳族化合物（请参见方案； SA =比活度）。

  DOI：

  10.1002/anie.201002310

文献信息

• N-fluorosulfonimides and their application as fluorinating agents
  申请人：Allied-Signal Inc.

  公开号：US05254732A1

  公开（公告）日：1993-10-19

  The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.

  该发明描述了N-氟磺酰亚胺，它们作为氟化试剂很有用。这些N-氟磺酰亚胺稳定，易于合成，并且可以在温和条件下将氟引入有机化合物中。
• <i>p</i>-Toluenesulfonic acid catalysed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centres
  作者：Shi-Zhong Tang、Hong-Li Bian、Zong-Song Zhan、Meng-En Chen、Jian-Wei Lv、Shaolei Xie、Fu-Min Zhang

  DOI：10.1039/c8cc06643d

  日期：——

  A p-toluenesulfonic acid catalyzed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centers has been developed, featuring a broad substrate scope, environmentally benign reaction conditions, and operational simplicity.

  已开发出一种对甲苯磺酸催化的α-支链酮氟化物，用于构建氟化季碳中心，具有广泛的底物范围，对环境无害的反应条件和操作简便性。
• Catalyst-Free Decarboxylative Fluorination of Tertiary β-Keto Carboxylic Acids
  作者：Kazutaka Shibatomi、Misaki Katada、Kazumasa Kitahara、Seiji Iwasa

  DOI：10.1055/s-0037-1611019

  日期：2018.11

  Decarboxylative fluorination of tertiary β-keto carboxylic ­acids was performed using an electrophilic fluorinating reagent. The reaction proceeded in the absence of a catalyst or base to yield the corresponding α-fluoroketones with tertiary fluorocarbons in good to high yields. Considering that the α-fluorination of asymmetrical ketones ­often causes problems with the regioselectivity between the

  使用亲电子氟化试剂进行叔 β-酮羧酸的脱羧氟化。该反应在不存在催化剂或碱的情况下进行，以良好至高产率产生相应的α-氟代酮和叔碳氟化合物。考虑到不对称酮的 α-氟化通常会导致 α-和 α'-位之间的区域选择性问题，该方法可能是合成叔氟酮的简单酮的 α-氟化的良好替代方法。
• Synthesis and reactivity of [¹⁸F]-N-fluorobenzenesulfonimide
  作者：Harriet Teare、Edward G. Robins、Erik Årstad、Sajinder K. Luthra、Véronique Gouverneur

  DOI：10.1039/b701177f

  日期：——

  A novel [18F]NF reagent and two novel radiochemical transformations have been developed: [18F]NFSi has been prepared from sodium dibenzenesulfonimide and reacted in the presence of silyl enol ethers and allylsilanes to deliver labelled fluorinated ketones and allylic fluorides respectively; the radiosynthesis of the fluorinated A ring of vitamin D3 has also been completed with success.

  一种新型[18F]NF 试剂和两种新型放射化学转化方法已经研制成功：以二苯磺酰亚胺钠为原料制备了[18F]NFSi，并在硅基烯醚和烯丙基硅烷存在下发生反应，分别生成了标记的氟化酮和烯丙基氟化物；维生素 D3 的氟化 A 环的放射合成也已成功完成。
• New fluorinating reagents - I. The first enantioselective fluorination reaction
  作者：Edmond Differding、Robert W. Lang

  DOI：10.1016/s0040-4039(00)82271-6

  日期：——

  Crystalline, optically pure N-fluoro sultams (−)-3 and (+)-5 are the first examples of enantioselective fluorinating reagents. Thus unprecedented enantiomeric excesses up to 70% are observed when various prochiral metal enolates are fluorinated by using these new reagents.

  结晶，光学纯净的N-氟磺胺（-）-3和（+）-5是对映选择性氟化试剂的第一个实例。因此，当使用这些新试剂对各种手性金属烯醇化物进行氟化时，观察到前所未有的对映体过量，最高可达70％。