(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate | 402757-16-8

• 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: (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate
• 英文别名: 2-(trifluoromethyl)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 402757-16-8
• 化学式: C₁₁H₁₅F₃O₄
• 分子量: 268.233
• InChiKey: NZDKTTUAJFSRRH-ZETCQYMHSA-N

物化性质

• 沸点：
  297.2±40.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate 在 10percent Pd/C 咪唑 、 盐酸 、 sodium sulfide 、 sodium tetrahydroborate 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 66.33h， 生成 (2R,4S)-tert-butyldimethyl-4-(trifluoromethyl-tetrahydro-thiophen-2-ylmethoxy)silane
  参考文献：
  名称：

  Synthesis of Novel l-2‘,3‘-Dideoxy-2‘-trifluoromethyl-4‘- thiocytidines from α-Trifluoromethyl-α,β-unsaturated Ester

  摘要：

  A short and efficient synthesis of L-2',3'-dideoxy-2 -trifluoromethyl-4'-thiocytidines is described. (2R,4S/2S,4S)5-(tert-Butyldimethylsiloxy)-2-trifluoromethylpentan-4- olide (3a and 3b) are prepared from alpha-trifluoromethyl-alpha,beta-unsaturated ester (1) in three steps and converted to compounds 6a and 6b. The corresponding 1-O-acetyl derivatives 8a and 8b were obtained via the usual Pummerer rearrangement from 6a and 6b in two steps, which were in turn used to synthesize L-4'-thiocytidines 10a and 10b.

  DOI：

  10.1021/jo0159690
• 作为产物：
  描述：

  氟磺酰基二氟乙酸甲酯 、 ethyl (S,E)-2-bromo-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-enoate 在 六甲基磷酰三胺 、 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate
  参考文献：
  名称：

  A one-pot synthesis of (E)-α-bromo-α,β-unsaturated esters and their trifluoromethylation: a general and stereoselective route to (E)-α-trifluoromethyl-α,β-unsaturated esters

  摘要：

  Bromination of a phosphonate anion derived in situ from ethyl bis (2,2 2 -trifluoroethyl)phosphonoacetate 3 followed by the addition of aldehydes produced (E)-alpha -bromo-alpha,beta -unsaturated esters 5 stereo selectively. The treatment of 5 with FSO2CF2CO2Me and CuI in DMF/HMPA provided (E)-alpha -trifluoromethyl-alpha,beta -unsaturated esters 6. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01153-4

文献信息

• A new route to α-trifluoromethyl-α,β-unsaturated esters
  作者：Xingang Zhang、Feng-Ling Qing、Yonggang Yang、Jiang Yu、Xiang-Kai Fu

  DOI：10.1016/s0040-4039(00)00279-3

  日期：2000.4

  The treatment of α-bromo-α,β-unsaturated esters with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters.

  在DMF / HMPA中用FSO 2 CF 2 CO 2 Me和CuI处理α-溴-α，β-不饱和酯构成了制备α-三氟甲基-α，β-不饱和酯的新合成方案。
• Synthesis of 2‘,3‘-Dideoxy-2‘-trifluoromethylnucleosides from α-Trifluoromethyl-α,β-unsaturated Ester
  作者：Xingang Zhang、Feng-Ling Qing、Yihua Yu

  DOI：10.1021/jo005520r

  日期：2000.10.1

  beta-unsaturated esters 3. The trifluoromethylation of (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (2e), which is derived from 1-(R)-glyceraldehyde acetonide, yields the key intermediate alpha-trifluoromethyl-alpha,beta-unsaturated esters 3e. This is transformed into anomeric acetates 8a and 8b and is used for the synthesis of a number of 2', 3'-dideoxy-2'-trifluoromethylnucleosides

  在DMF / HMPA中用FSO（2）CF（2）CO（2）Me和CuI处理α-溴-α，β-不饱和酯2构成了制备α-三氟甲基-α，β的新合成方案-不饱和酯3.（Z）/（E）-乙基3-[（（S）-2,2-二甲基-1,3-二氧戊环-4-基] -2-溴-2-丙酸酯（2e）的三氟甲基化衍生自1-（R）-甘油醛丙酮化物的）生成关键中间体α-三氟甲基-α，β-不饱和酯3e。将其转化为异头乙酸酯8a和8b，并用于合成许多2'，3'-二脱氧-2'-三氟甲基核苷。
• Synthesis and Antiviral Evaluation of Novel 4′-Trifluoromethylated 5′-Deoxyapiosyl Nucleoside Phosphonic Acids
  作者：Seyeon Kim、Eunae Kim、Wonjae Lee、Joon Hee Hong

  DOI：10.1080/15257770.2014.938753

  日期：2014.12.2

  On the basis of the discovery that the threosyl nucleoside phosphonate PMDTA is a potent anti-HIV compound, we synthesized several 4 '-trifluoromethyl-5 '-deoxyapiosyl nucleoside phosphonic acids and evaluated their anti-HIV activity. An efficient synthetic route was optimized, starting from an alpha-trifluoromethyl-alpha,beta-unsaturated ester. Glycosylation of the purine nucleosidic bases with a glycosyl donor yielded modified nucleoside intermediates, which were then phosphonated and hydrolyzed to provide the targeted nucleoside analogs. Once synthesized, the anti-HIV and cytotoxic activities of each analog were evaluated. None of the analogs showed significant anti-HIV activity at concentrations up to 100 mu M.