2,2,2-trifluoroethyl decanoate | 52626-69-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,2,2-trifluoroethyl decanoate
• CAS: 52626-69-4
• 化学式: C₁₂H₂₁F₃O₂
• 分子量: 254.293
• InChiKey: JCZKMNDMYRZOTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  180 °C(Press: 10 Torr)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl decanoate 在 吡啶 、 Pseudomonas cepacia lipase 作用下， 反应 4.0h， 生成 Decanoic acid (2R,3R,4S,5R,6R)-6-((S)-2-decanoyloxy-1-hydroxymethyl-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Bioactive glycoglycerolipid analogues: an expeditious enzymatic approach to mono- and diesters of 2-O-β-d-galactosylglycerol

  摘要：

  2-O-beta-D-Galactosylglycerol 1 was submitted to acylation using Pseudomonas cepacia or Candida antarctica lipases as catalysts and 2,2,2-trifluoroethyl esters of butanoic, hexanoic, octanoic or decanoic acid as acyl carriers. Taking advantage of the high diastereoselectivity and regioselectivity of the two enzymes, the 1-O-, 3-O-, 6'-O-acyl and the 1,6'-di-O-acylderivatives of 1 were obtained pure or in an appreciably enriched form. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00207-9
• 作为产物：
  描述：

  2-重氮基-1,1,1-三氟乙烷 、 正癸酸 在 tetrafluoroboric acid 作用下， 以 氘代氯仿 为溶剂， 以95%的产率得到2,2,2-trifluoroethyl decanoate
  参考文献：
  名称：

  Acid-catalyzed reactions of 2,2,2-trifluorodiazoethane for analysis of functional groups by fluorine-19 nuclear magnetic resonance spectrometry

  摘要：

  DOI：

  10.1021/ac00240a040

文献信息

• Lipase-Catalyzed 1,6-Acylation of D-Mannitol
  作者：Peter J. Duggan、David G. Humphrey、Victoria McCarl

  DOI：10.1071/ch04040

  日期：——

  The selective synthesis of 1,6-diacyl d-mannitols from 2,2,2-trifluoroethyl esters using transesterification, catalyzed by lipases, has been investigated, and the results have been compared with those obtained from a typical acid chloride procedure and a phenylboronic acid-assisted approach. Three commercially available lipases and five 2,2,2-trifluoroethyl esters were examined. In most cases, the yields obtained from the lipase reactions were superior to those produced from either of the other two methods.

  研究人员利用脂肪酶催化的酯交换反应从 2,2,2-三氟乙酯中选择性地合成了 1,6-二乙酰基 d-甘露醇，并将结果与典型的氯化酸程序和苯硼酸辅助方法所获得的结果进行了比较。研究考察了三种市售脂肪酶和五种 2,2,2-三氟乙基酯。在大多数情况下，脂肪酶反应的产率都优于其他两种方法。
• Synthesis of <i>N</i>-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
  作者：Marco Zuccolo、Giulia Orsini、Martina Quaglia、Luca Mirra、Cristina Corno、Nives Carenini、Paola Perego、Diego Colombo

  DOI：10.1039/d3ob00891f

  日期：——

  N-Oxyamides of bioactive anionic glycoglycerolipids based on 2-O-β-D-glucosylglycerol were efficiently prepared. However, the oxidation step of the primary hydroxyl group of the glucose moiety in the presence of the N-oxyamide function appeared to be a difficult task that was nevertheless conveniently achieved for the first time by employing a chemoenzymatic laccase/TEMPO procedure. The obtained N-oxyamides

  有效制备了基于2- O -β- D-葡萄糖基甘油的生物活性阴离子甘油脂的N-草酰胺。然而，在N-草酰胺官能团存在下，葡萄糖部分的伯羟基的氧化步骤似乎是一项艰巨的任务，但首次通过采用化学酶漆酶/TEMPO程序方便地实现了这一任务。与相应的生物活性酯类似，所获得的N-羟基酰胺在无血清培养基中比在完全培养基中表现出更高的对卵巢癌IGROV-1细胞增殖的抑制作用。稳定性和血清结合研究表明，在完全培养基中观察到的化合物活性降低可能主要是由于血清蛋白的结合作用，而不是糖甘油脂酰基链的水解降解。此外，无血清条件下的细胞研究结果表明，N-羟基酰胺基团可以增加甘油糖脂的抗增殖活性，而与阴离子羧基的存在无关。除 IGROV-1 之外的其他细胞系的细胞研究也支持该系列化合物对 Akt 过度激活的肿瘤细胞具有一定程度的选择性。
• Carrea, Giacomo; Riva, Sergio; Secundo, Francesco, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1057 - 1061
  作者：Carrea, Giacomo、Riva, Sergio、Secundo, Francesco、Danieli, Bruno

  DOI：——

  日期：——
• A facile lipase catalyzed access to fatty acid monoesters of
  作者：Diego Colombo、Fiamma Ronchetti、Antonio Scala、Ida M. Taino、Lucio Toma

  DOI：10.1016/0957-4166(96)00073-0

  日期：1996.3

  2-O-beta-D-glucopyranosylglycerol was submitted to acylation using Pseudomonas cepacia lipase as catalyst and 2,2,2-trifluoroethyl esters of various long chain carboxylic acids as acyl carriers. Monoacylation was easily accomplished with preferred formation of the (2S)-1-O-acyl derivatives in reactions showing high regio- and diastereoselectivity. (C) 1996 Elsevier Science Ltd
• Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol
  作者：Diego Colombo、Federica Compostella、Fiamma Ronchetti、Antonio Scala、Lucio Toma、Harukuni Tokuda、Hoyoku Nishino

  DOI：10.1016/s0968-0896(99)00137-6

  日期：1999.9

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.