catechine (2R-cis)-TMS

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: catechine (2R-cis)-TMS
• 英文别名: Silane, [[2-[3,4-bis[(trimethylsilyl)oxy]phenyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triyl]tris(oxy)]tris[trimethyl-, (2R-cis)-；trimethyl-[2-trimethylsilyloxy-4-[(2S,3S)-3,5,7-tris(trimethylsilyloxy)-3,4-dihydro-2H-chromen-2-yl]phenoxy]silane
• 化学式: C₃₀H₅₄O₆Si₅
• 分子量: 651.183
• InChiKey: QKMSLFRFGOTVEJ-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.44
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 (+)-表儿茶素 以 乙腈 为溶剂， 反应 0.5h， 生成 catechine (2R-cis)-TMS
  参考文献：
  名称：

  Cyclic ions in the mass spectra of trimethylsilyl derivatives of substitutedo-dihydroxybenzenes

  摘要：

  AbstractThe mass spectra of trimethylsilyl (TMS) ethers/methyl esters of phenolic acids containing o‐dihydroxybenzene groups have base peaks at [M−119]+ instead of the usual [M−15]+ and [M−31]+ that are characteristic of TMS/methyl esters of monohydroxyphenolic acids. These ions, formed by the loss of 31+88 u from the parent ion, possess a cyclic moiety as proven by substitution of deuterium atoms for hydrogen atoms in the TMS groups of the methyl esters of 3,4,5‐trihydroxybenzoic (gallic), 3,4‐dihydroxybenzoic (protocatechuic) and β‐(3,4‐dihydroxyphenyl)propenoic (caffeic) acids. Although these cyclic ions are the base peaks in TMS‐derivatized o‐dihydroxyphenolic acid esters, similar ions represent intense peaks but not necessarily the base peak in other derivatized compounds such as 1,2‐dihydroxybenzene, 1,2‐dihydroxy‐3‐methyl‐ and 1,2‐dihydroxy‐4‐methyl‐benzenes and flavan‐3‐ols that possess o‐dihydroxybenzene groups. Compounds possession m‐ or p‐dihydroxybenzene groups do not form these cyclic ions; therefore, this procedure for derivatization and interpretation of mass spectra is valuable for the identification of compounds containing o‐dihydroxybenzene groups in complex mixtures of isomeric compounds.

  DOI：

  10.1002/oms.1210181002

文献信息

• Cyclic ions in the mass spectra of trimethylsilyl derivatives of substitutedo-dihydroxybenzenes
  作者：Robert J. Horvat、Samuel D. Senter

  DOI：10.1002/oms.1210181002

  日期：1983.10

  AbstractThe mass spectra of trimethylsilyl (TMS) ethers/methyl esters of phenolic acids containing o‐dihydroxybenzene groups have base peaks at [M−119]+ instead of the usual [M−15]+ and [M−31]+ that are characteristic of TMS/methyl esters of monohydroxyphenolic acids. These ions, formed by the loss of 31+88 u from the parent ion, possess a cyclic moiety as proven by substitution of deuterium atoms for hydrogen atoms in the TMS groups of the methyl esters of 3,4,5‐trihydroxybenzoic (gallic), 3,4‐dihydroxybenzoic (protocatechuic) and β‐(3,4‐dihydroxyphenyl)propenoic (caffeic) acids. Although these cyclic ions are the base peaks in TMS‐derivatized o‐dihydroxyphenolic acid esters, similar ions represent intense peaks but not necessarily the base peak in other derivatized compounds such as 1,2‐dihydroxybenzene, 1,2‐dihydroxy‐3‐methyl‐ and 1,2‐dihydroxy‐4‐methyl‐benzenes and flavan‐3‐ols that possess o‐dihydroxybenzene groups. Compounds possession m‐ or p‐dihydroxybenzene groups do not form these cyclic ions; therefore, this procedure for derivatization and interpretation of mass spectra is valuable for the identification of compounds containing o‐dihydroxybenzene groups in complex mixtures of isomeric compounds.