3-fluoro-3,7-dimethylocta-1,6-diene | 125081-51-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-fluoro-3,7-dimethylocta-1,6-diene
• 英文别名: linaloyl fluoride
• CAS: 125081-51-8
• 化学式: C₁₀H₁₇F
• 分子量: 156.243
• InChiKey: FCVNMMHXAZKIHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-fluoro-3,7-dimethylocta-1,6-diene 以 氘代氯仿 为溶剂， 反应 445.0h， 以60%的产率得到4-(1-fluoro-1-methylethyl)-1-methylcyclohexene
  参考文献：
  名称：

  关于纯净烯丙基氟的分离

  摘要：

  整齐肉桂氟化物，香叶基氟化物，5-甲酯基-3- fluorocyclohexene和父3- fluorocyclohexene经历与硼硅酸盐玻璃或适度强酸，其由在与消除HF的缩聚被F的电抽象引发催化量接触自发分解- 。这些烯丙基氟的酸敏感性与各个烯丙基阳离子的稳定性相关，超过母体苄基氟的敏感性，但是可以通过使用允许它们在纯净状态下分离和处理的Teflon和PFA容器来减轻。

  DOI：

  10.1016/j.jfluchem.2009.02.012
• 作为产物：
  描述：

  芳樟醇 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到3-fluoro-3,7-dimethylocta-1,6-diene
  参考文献：
  名称：

  在连续流动微反应器中使用二乙氨基三氟化硫 (DAST) 进行氟化

  摘要：

  描述了在连续流动微反应器中方便和安全地使用二乙氨基三氟化硫作为氟化剂，使用在线纯化方法获得清洁的反应产物。

  DOI：

  10.1055/s-2008-1078026

文献信息

• Development of fluorination methods using continuous-flow microreactors
  作者：Marcus Baumann、Ian R. Baxendale、Laetitia J. Martin、Steven V. Ley

  DOI：10.1016/j.tet.2009.05.083

  日期：2009.8

  The safe and reliable use of various fluorination methods including nucleophilic fluorination (DAST), trifluoromethylation (Ruppert's reagent) and electrophilic fluorination (Selectfluor®) in a continuous-flow microreactor is reported. Special attention was given to the use of in-line scavenging procedures in order to obtain clean products without the need for further purification.

  安全可靠的使用各种氟化方法，包括核氟化（DAST），三氟甲基化（鲁珀特试剂）和电氟化（的Selectfluor ®报道在连续流微反应器）。为了获得清洁的产品而无需进一步纯化，特别注意了使用在线清除程序。
• Synthesis of alkyl halides under neutral conditions
  作者：François Munyemana、Anne-Marie Frisque-Hesbain、Alain Devos、Léon Ghosez

  DOI：10.1016/s0040-4039(00)99407-3

  日期：1989.1

  Primary and secondary alcohols are efficiently converted to the corresponding alkyl halides under neutral conditions.

  伯醇和仲醇在中性条件下可有效地转化为相应的烷基卤。
• Iridium-Catalyzed Allylic Fluorination of Trichloroacetimidates
  作者：Joseph J. Topczewski、Timothy J. Tewson、Hien M. Nguyen

  DOI：10.1021/ja2087213

  日期：2011.12.7

  allylic fluorination method utilizing trichloroacetimidates in conjunction with an iridium catalyst has been developed. The reaction is conducted at room temperature under ambient air and relies on Et(3)N·3HF reagent to provide branched allylic fluorides with complete regioselectivity. This high-yielding reaction can be conducted on a multigram scale and shows considerable functional group tolerance

  已经开发了一种利用三氯乙酰亚胺酯与铱催化剂结合的快速烯丙基氟化方法。该反应在室温和环境空气中进行，依靠 Et(3)N·3HF 试剂提供具有完全区域选择性的支链烯丙基氟化物。这种高产率反应可以在数克规模上进行，并显示出相当大的官能团耐受性。[(18)F]KF·Kryptofix 的使用允许在 10 分钟内加入 (18)F(-)。
• Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling^,
  作者：Alexandre L’Heureux、Francis Beaulieu、Christopher Bennett、David R. Bill、Simon Clayton、François LaFlamme、Mahmoud Mirmehrabi、Sam Tadayon、David Tovell、Michel Couturier

  DOI：10.1021/jo100504x

  日期：2010.5.21

  Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-H F and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et3N center dot 3HF, Et3N center dot 2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.
• Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols
  作者：Justyna Walkowiak、Magdalena Tomas-Szwaczyk、Günter Haufe、Henryk Koroniak

  DOI：10.1016/j.jfluchem.2012.07.011

  日期：2012.11

  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.