1-fluorododecan-2-ol | 132547-33-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 1-fluorododecan-2-ol
• CAS: 132547-33-2
• 化学式: C₁₂H₂₅FO
• 分子量: 204.328
• InChiKey: SIXHNKZQLHNSGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-fluorododecan-2-ol 在 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 作用下， 以 十二烷 为溶剂， 反应 0.17h， 以63%的产率得到1,2-difluorododecane
  参考文献：
  名称：

  Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine

  摘要：

  Deoxyfluorination of alcohols was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.089
• 作为产物：
  描述：

  1,2-环氧十二烷 在 KH₂F₃ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 32.0h， 生成 2-氟十二烷-1-醇 、 1-fluorododecan-2-ol
  参考文献：
  名称：

  三氟化二氢钾：用于环氧化物开环的新型氟化剂

  摘要：

  已经发现，三氟化二氢钾是一种有效且易于处理的固体试剂，用于环氧化物和立体选择性地产生氟代醇的环氧化物的开环反应。该反应通过将HF顺式加成到环氧化物上而进行。

  DOI：

  10.1016/0022-1139(94)03175-y

文献信息

• Potassium dihydrogen trifluoride: a novel fluorinating reagent for ring-opening of epoxides
  作者：Masanori Tamura、Motonari Shibakami、Takashi Arimura、Shigeru Kurosawa、Akira Sekiya

  DOI：10.1016/0022-1139(94)03175-y

  日期：1995.1

  It has been found that potassium dihydrogen trifluoride is an efficient and easy-to-handle solid reagent for the ring-opening reaction of epoxides giving fluorohydrins regio- and stereo-selectively. The reaction proceeds via cis-addition of HF to the epoxide.

  已经发现，三氟化二氢钾是一种有效且易于处理的固体试剂，用于环氧化物和立体选择性地产生氟代醇的环氧化物的开环反应。该反应通过将HF顺式加成到环氧化物上而进行。
• Tetrabutylammonium dihydrogentrifluoride: an efficient catalyst for regio and stereoselective conversion of epoxides to fluorohydrins under solid-liquid phase-transfer catalysis conditions.
  作者：Dario Landini、Michele Penso

  DOI：10.1016/s0040-4039(00)97281-2

  日期：1990.1

  Tetrabutylammonium dihydrogentrifluoride is an efficient and easy-to-handle hydrofluorinating agent in the ring-opening reaction of oxiranes to give good or excellent yields of fluorohydrins under solid-liquid PTC conditions.

  四丁基三氟化氢铵在环氧乙烷的开环反应中是一种高效且易于处理的氢氟化剂，在固液PTC条件下可获得良好或优异的氟代醇收率。
• The effect of triphenylphosphine on ring-opening of aliphatic epoxides with potassium fluoride-poly (hydrogen fluoride)
  作者：Masanori Tamura、Motonari Shibakami、Akira Sekiya

  DOI：10.1016/s0022-1139(97)00069-9

  日期：1997.10

  The ring-opening reaction of aliphatic epoxides with potassium fluoride-poly (hydrogen fluoride) is enhanced by a catalytic amount of triphenylphosphine. It is assumed that phosphonium fluoride species formed from triphenylphosphine work as fluorinating agents in this reaction.

  催化量的三苯膦可增强脂肪族环氧化物与氟化钾-聚（氟化氢）的开环反应。假定由三苯基膦形成的氟化phospho物质在该反应中起氟化剂的作用。
• <i>N</i>,<i>N’</i>‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions
  作者：Tsugio Kitamura、Daichi Kitamura、Juzo Oyamada、Masahiro Higashi、Yosuke Kishikawa

  DOI：10.1002/adsc.202300265

  日期：2023.8.15

  iodoarene-catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3-dicarbonyl compounds, giving 1,2-difluorinated alkanes, geminal difluorinated compounds, 2-fluorinated-1,3-dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues

  报道了一种新的 N−F 试剂，N , N '-二氟-2,2'-联吡啶鎓双（四氟硼酸盐），作为末端氧化剂用于碘芳烃催化的氟化反应。该反应可有效氟化简单烯烃、芳香烯烃和1,3-二羰基化合物，分别以良好至高产率生成1,2-二氟化烷烃、偕二氟化化合物、2-氟化-1,3-二羰基化合物。这是一种有用的氟化反应，不仅改善了使用传统 mCPBA 作为末端氧化剂的氟化反应的问题，而且构建了更简单的催化循环。本发明的NF试剂可以作为2,2'-联吡啶回收。
• Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine
  作者：Shingo Kobayashi、Atushi Yoneda、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1016/j.tet.2004.05.089

  日期：2004.8

  Deoxyfluorination of alcohols was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.