[(1S)-1-cyanopropyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 126227-58-5

• 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: [(1S)-1-cyanopropyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 126227-58-5
• 化学式: C₁₄H₁₄F₃NO₃
• 分子量: 301.265
• InChiKey: RUMVGECIPZOMGI-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 氰化四丁基铵 作用下， 生成 [(1R)-1-cyanopropyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 、 [(1S)-1-cyanopropyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  A new asymmetric synthesis of cyanohydrins and oxygen-functionalized derivatives: stereoselective addition of cyanide to chiral rhenium aldehyde and ketone complexes of the formula [(.eta.5-C5H5)Re(NO)(PPh3)(O:CRR')]+BF4-

  摘要：

  Reactions of racemic and optically active pi aldehyde complexes [(eta-5-C5H5)Re(NO)(PPh3)(eta-2-O = CHR)]+ BF4- (1; R = a, CH3; b, CH2CH3; c, CH(CH3)2; d, CH2C6H5; e, C6H5) with (CH3CH2)4N+ CN- (CH2Cl2, -80-degrees-C) give cyanohydrin alkoxide complexes (eta-5-C5H5)Re(NO)(PPh3)(OCH(CN)R) (3a-e, 78-95%) in 89-53% de. Subsequent reactions of (+)-(RS)-3a-e with (-)-(R)-C6H5(CH3O)(F3C)CC(= O)Cl (MTPA-Cl) and DMAP in C6H6 give optically active esters MTPA-OCH(CN)R (96-85%; 90-56% de). Analogous reactions of racemic sigma-methyl ketone complexes [(eta-5-C5H5)Re(NO)(PPh3)(eta-1-O = C(CH3)R)]+ BF4- (2; R = a, CH3; b, CH2CH3; c, CH(CH3)2; d, C(CH3)3; e, C6H5) and (CH3CH2)4N+ CN- give alkoxide complexes (eta-5-C5H5)Re(NO)(PPh3)(OCCH3(CN)R) (5a-e, 60-88%) in 71-99% de. A similar reaction of 2e and (CH3)3SiC = CLi gives (eta-5-C5H5)Re(NO)(PPh3)(OCCH3(C = CSi(CH3)3)C6H5) (88%) in 94% de. Mechanisms of diastereoselection are briefly discussed.

  DOI：

  10.1021/jo00024a023

文献信息

• Stereoselective addition of cyanide ion to chiral rhenium π-aldehyde complexes of the formulae [(η5-C5H5)Re(NO)(PPh3)(η2-OCHR)]+ BF4−
  作者：Charles M. Garner、Jesus M. Fernández、J.A. Gladysz

  DOI：10.1016/s0040-4039(00)99287-6

  日期：——