1-fluorooct-2-ene | 947546-81-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-fluorooct-2-ene
• CAS: 947546-81-8
• 化学式: C₈H₁₅F
• 分子量: 130.206
• InChiKey: IHJITRFKEFESAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-辛烯-3-醇 、 以 二氯甲烷 为溶剂， 反应 14.0h， 以36%的产率得到3-fluorooct-1-ene
  参考文献：
  名称：

  Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols

  摘要：

  A new, mild method to prepare alpha-trifluoromethylated amides bearing an additional trans-configured double bond in gamma-position is described. Treatment at room temperature of fluorinated and non-fluorinated allylic alcohols 1 and 2 with the 1,1,3,3,3-pentafluoropropene-diethylamine adduct (PFPDEA) in the presence of triethylamine as base gave the products of [3,3]-sigmatropic Eschenmoser-Claisen-type rearrangements with good yields and excellent diastereoselectivity due to chair-like conformations of transition states. Starting with enantiomerically enriched allylic alcohols chirality transfer from carbon 3 of the allylic system to carbon 2 of the final alpha-trifluoromethyl carboxamides was observed. This methodology was applied to both simple and more complex, including terpenic, allylic alcohols and might be developed to an alternative strategy to the well-known electrophilic alpha-trifluoromethylation of carbonyl compounds. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.07.011

文献信息

• PREPARATION OF (THREO)-1-ARYL-2-ACYLAMIDO-3-FLUORO-1-PROPANOLS
  申请人：SCHERING CORPORATION

  公开号：EP0200739A1

  公开（公告）日：1986-11-12
• US4582918A
  申请人：——

  公开号：US4582918A

  公开（公告）日：1986-04-15
• US4677214A
  申请人：——

  公开号：US4677214A

  公开（公告）日：1987-06-30
• US4973750A
  申请人：——

  公开号：US4973750A

  公开（公告）日：1990-11-27
• [EN] PREPARATION OF (THREO)-1-ARYL-2-ACYLAMIDO-3-FLUORO-1-PROPANOLS
  申请人：SCHERING CORPORATION

  公开号：WO1986001799A1

  公开（公告）日：1986-03-27

  (EN) A novel sequence of highly selective chemical reactions for conversion of 3-Aryl-2-propyn-1-ols into $i(cis)-1-Aryl-3-fluoro-1-propene and into D,L-(threo)-1-Aryl-2-acylamido-3-fluoro-1-propanols. Preparation of D-(threo)-1-Aryl-2-acylamido-3-fluoro-1-propanol antibacterial agents including the D-(threo)-3-fluoro-3-deoxy derivatives of chloramphenicol and thiamphenicol.(FR) Nouvelle séquence de réactions chimiques hautement sélectives pour la conversion de 3-Aryl-2-propyn-1-ols en $i(cis)-1-Aryl-3-fluoro-1-propène et en D,L-(thréo)-1-Aryl-2-acylamido-3-fluoro-1-propanols. Préparation d'agents antibactériens à base de D-(thréo)-1-Aryl-2-acylamido-3-fluoro-1-propanol comprenant les dérivés D-(thréo)-3-fluoro-3-désoxy de chloramphénicol et thiamphénicol.