benzyl pentafluoropropionate | 76008-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl pentafluoropropionate
• 英文别名: benzyl perfluoropropionate；benzyl 2,2,3,3,3-pentafluoropropanoate
• CAS: 76008-52-1
• 化学式: C₁₀H₇F₅O₂
• 分子量: 254.156
• InChiKey: DBXZPAFJFMNYKG-UHFFFAOYSA-N

物化性质

• 沸点：
  80-81 °C(Press: 21 Torr)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丙烷-1-硫醇 、 benzyl pentafluoropropionate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到benzyl propyl sulfide
  参考文献：
  名称：

  Formation of C–S Bond by the Elimination of Perfluorocarboxylic Acid

  摘要：

  Thiirane可以通过与三乙胺的分子内消除反应，方便地从2-巯基乙基三氟乙酸酯或五氟丙酸酯生成。烷基苄基硫化物也可以通过与苄基三氟乙酸酯或五氟丙酸酯和烷基硫醇的分子间消除反应合成。

  DOI：

  10.1246/bcsj.53.2097
• 作为产物：
  描述：

  五氟丙硫酸乙酯 、 苯甲醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以85%的产率得到benzyl pentafluoropropionate
  参考文献：
  名称：

  Ethyl pentafluoropropanethioate: A useful pentafluoropropionylating agent for amines and alcohols

  摘要：

  DOI：

  10.1016/s0022-1139(00)82321-0

文献信息

• Reactions of Perfluoro-2-methyl-2-pentene with Carboxylic Acids, Alcohols, and Some Cyclic Amides. A New Fluorinating Reagent
  作者：Shozo Yanagida、Yukihiro Noji、Mitsuo Okahara

  DOI：10.1246/bcsj.54.1151

  日期：1981.4

  l-3-acyloxy-2-pentene (4), the yields changing with base, solvent, phase-transfer catalyst, and their combination. In the presence of triethylamine, fluorination occurs exclusively, producing acid fluorides in good yields. Alcohols and 2-pyridone are converted into alkyl fluorides and 2-fluoropyridine, respectively, with use of triethylamine as a base with an aprotic solvent. The reactions of PMP with

  全氟-2-甲基-2-戊烯 (PMP) 与羧酸、醇和 2-吡啶酮反应，生成 Michaeltype 加成产物，1,1,1,3,4,4,5,5,5-nonafluoro-2 -trifluoromethyl-3-acyloxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-alkoxypentane, 1,1,1,3,4,4,5,5 ,5-nonafluoro-2-trifluoromethyl-3 (2-pyridyloxy)pentane，分别以良好的收率。在碱存在下，羧酸生成酰氟、1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-pentanone 和 1,1,1,4,4,5 ,5,5-octafluoro-2-trifluoromethyl-3-acyloxy-2-pentene
• Perfluoroalcohols
  作者：Yuri Cheburkov、Gerald J. Lillquist

  DOI：10.1016/s0022-1139(02)00204-x

  日期：2002.12

  Perfluorinated primary alcohol adducts with triethylamine were prepared from lower perfluorinated acid fluorides and triethylamine monohydrofluoride. They are stable compounds and may be used as a source of RFO groups in organic syntheses.

  由低级全氟化酰基氟和三乙胺一氢氟化物制备与三乙胺的全氟化伯醇加合物。它们是稳定的化合物，可以用作有机合成中R F O基团的来源。
• Inhibition of Sphingosine-1-Phosphate Lyase for the Treatment of Autoimmune Disorders
  作者：Jeffrey T. Bagdanoff、Michael S. Donoviel、Amr Nouraldeen、James Tarver、Qinghong Fu、Marianne Carlsen、Theodore C. Jessop、Haiming Zhang、Jill Hazelwood、Huy Nguyen、Simon D. P. Baugh、Michael Gardyan、Kristen M. Terranova、Joseph Barbosa、Jack Yan、Mark Bednarz、Suman Layek、Lawrence F. Courtney、Jerry Taylor、Ann Marie Digeorge-Foushee、Suma Gopinathan、Debra Bruce、Traci Smith、Liam Moran、Emily O’Neill、Jeff Kramer、Zhong Lai、S. David Kimball、Qingyun Liu、Weimei Sun、Sean Yu、Jonathan Swaffield、Alan Wilson、Alan Main、Kenneth G. Carson、Tamas Oravecz、David J. Augeri

  DOI：10.1021/jm900278w

  日期：2009.7.9

  During nearly a decade of research dedicated to the study of sphingosine signaling pathways, we identified sphingosine-1-phosphate lyase (S1PL) as a drug target for the treatment of autoimmune disorders. S1PL catalyzes the irreversible decomposition of sphingosine-1-phosphate (S1P) by a retro-aldol fragmentation that yields hexadecanaldehyde and phosphoethanolamine. Genetic models demonstrated that mice expressing reduced S1PL activity had decreased numbers of circulating lymphocytes due to altered lymphocyte trafficking, which prevented disease development in multiple models of autoimmune disease. Mechanistic studies of lymphoid tissue following oral administration of 2-acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxybutyl)-imidazole (THI) 3 showed a clear relationship between reduced lyase activity, elevated S I P levels, and lower levels of circulating lymphocytes. Our internal medicinal chemistry efforts discovered potent analogues of 3 bearing heterocycles as chemical equivalents of the pendant carbonyl present in the parent structure. Reduction of S1PL activity by oral administration of these analogues recapitulated the phenotype of mice with genetically reduced S1PL expression.
• KAWA HAJIMU; ISHIKAWA NOBUO, BULL. CHEM. SOC. JAP., 1980, 53, NO 7, 2097-2098
  作者：KAWA HAJIMU、 ISHIKAWA NOBUO

  DOI：——

  日期：——
• KAWA HAJIMU; ISHIKAWA NOBUO, J. FLUOR. CHEM., 1980, 16, NO 4, 365-372
  作者：KAWA HAJIMU、 ISHIKAWA NOBUO

  DOI：——

  日期：——