N-fluoro-3-chloro-5-(trifluoromethyl)pyridinium-2-sulfonate | 147541-09-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-fluoro-3-chloro-5-(trifluoromethyl)pyridinium-2-sulfonate
• 英文别名: 3-chloro-1-fluoro-5-(trifluoromethyl)pyridin-1-ium-2-sulfonate
• CAS: 147541-09-1
• 化学式: C₆H₂ClF₄NO₃S
• 分子量: 279.599
• InChiKey: DWZKLELWJVZAFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氧代环戊羧酸乙酯 、 N-fluoro-3-chloro-5-(trifluoromethyl)pyridinium-2-sulfonate 以 二氯甲烷 、 乙腈 为溶剂， 以75%的产率得到1-氟-2-氧代环戊烷-1-羧酸乙酯
  参考文献：
  名称：

  Certain substituted N-fluoropyridiniumsulfonates

  摘要：

  一种代替的N-氟吡啶磺酸盐的化学式为：##STR1## 其中R.sup.1是氢原子、卤素原子或C.sub.1 -C.sub.4烷基或卤代烷基基团，R.sup.2是C.sub.1 -C.sub.4烷基或卤代烷基基团，是一种有效的氟化剂。

  公开号：

  US05374732A1
• 作为产物：
  描述：

  2,3-二氯-5-三氟甲基吡啶 在 盐酸 、 fluorine 、 sodium sulfite 作用下， 以 乙腈 为溶剂， 反应 10.5h， 生成 N-fluoro-3-chloro-5-(trifluoromethyl)pyridinium-2-sulfonate
  参考文献：
  名称：

  Highly Selective Fluorinating Agents: a Counteranion-Bound N-Fluoropyridinium Salt System

  摘要：

  A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium-2-sulfonates 2a-h, differing in fluorinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent. N-Fluoropyridinium-3- and -4-sulfonates 3 and 4 were also synthesized. Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides. Thus, phenol, naphthol, phenylurethane, and the trimethylsilyl ether of phenol were exclusively or highly selectively fluorinated at the o-position with 2f-h. Conjugated enol trialkylsilyl ethers of a steroid were regioselectively fluorinated at the 6-position with moderately powerful 2b-e. This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive B-fluorination was achieved. Preferential beta-stereoselective fluorination at the 6-position was observed. N-Fluoropyridinium-2-sulfonates were activated with an acid. This acid-catalyzed fluorination led to the preferential p-fluorination of anisole. The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.

  DOI：

  10.1021/jo00125a049

文献信息

• 2-FLUORO-1,3-BENZODITHIOL 1,1,3,3-TETRAOXIDE DERIVATIVE, PRODUCTION METHOD THEREOF, AND PRODUCTION METHOD OF MONOFLUOROMETHYL GROUP-CONTAINING COMPOUND USING THE SAME
  申请人：Shibata Norio

  公开号：US20110319637A1

  公开（公告）日：2011-12-29

  A 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative as a monofluoromethyl group introduction agent that is effective as an intermediate in pharmaceutical and agrochemical synthesis, a production method thereof, and a production method of a monofluoromethyl group-containing compound using this 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative are provided. The 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative represented by the following general formula (1) (wherein R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a straight-chain or branched alkyl group having 1 to 4 carbon atoms, a straight-chain or branched alkyloxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group), the production method thereof, and various monofluoromethyl group-containing compounds are manufactured using this 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative as a monofluoromethylating agent.

  一种2-氟-1,3-苯二硫醚-1,1,3,3-四氧化物衍生物作为单氟甲基基团引入剂，可作为制药和农药合成中间体，提供其生产方法，以及使用该2-氟-1,3-苯二硫醚-1,1,3,3-四氧化物衍生物制备含单氟甲基基团的化合物的生产方法。所述2-氟-1,3-苯二硫醚-1,1,3,3-四氧化物衍生物由下述通用式（1）表示（其中R1、R2、R3和R4各自独立地表示氢原子、具有1至4个碳原子的直链或支链烷基基团、具有1至4个碳原子的直链或支链烷氧基基团、卤素原子、硝基团或氰基团），提供其生产方法，并使用该2-氟-1,3-苯二硫醚-1,1,3,3-四氧化物衍生物作为单氟甲基化剂制造各种含单氟甲基基团的化合物。
• Novel substituted N-Fluoropyridiniumsulfonate, intermediates therefor and preparation processes thereof
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：EP0526849A1

  公开（公告）日：1993-02-10

  A substituted N-fluoropyridiniumsulfonate of the formula: in which R1 is a hydrogen atom, a halogen atom or a C1-C4 alkyl or haloalkyl group, and R2 is a C1-C4 alkyl or haloalkyl group, which is an effective fluorinating agent.

  一种取代的 N-氟吡啶鎓磺酸盐，其式如下 其中 R1 是氢原子、卤素原子或 C1-C4 烷基或卤代烷基，R2 是 C1-C4 烷基或卤代烷基，它是一种有效的氟化剂。
• Substituted N-Fluoropyridiniumsulfonate, intermediates therefor and preparation processes thereof
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：EP0526849B1

  公开（公告）日：1999-12-01
• US5374732A
  申请人：——

  公开号：US5374732A

  公开（公告）日：1994-12-20
• US6855850B2
  申请人：——

  公开号：US6855850B2

  公开（公告）日：2005-02-15