2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl] | 10586-06-8

• 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: 2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl]
• 英文别名: 3,3',4',5,7-pentakis-O-trimethylsilyl-(+)-catechin；(2R-trans)-penta-TMS-catechin ether；catechine (2R-E)-TMS；(2R)-2r-(3,4-bis-trimethylsilanyloxy-phenyl)-3t,5,7-tris-trimethylsilanyloxy-chroman；(2R)-2r-(3,4-Bis-trimethylsilyloxy-phenyl)-3t,5,7-tris-trimethylsilyloxy-chroman；1(2H)-Benzopyran, 3,4-dihydro-2-[3,4-bis[(trimethylsilyl)oxy]phenyl]-3,5,7-tris[(trimethylsilyl)oxy]-, (2R-trans)-；trimethyl-[2-trimethylsilyloxy-4-[(2R,3S)-3,5,7-tris(trimethylsilyloxy)-3,4-dihydro-2H-chromen-2-yl]phenoxy]silane
• CAS: 10586-06-8；64138-54-1；64173-12-2；89267-68-5
• 化学式: C₃₀H₅₄O₆Si₅
• 分子量: 651.183
• InChiKey: QKMSLFRFGOTVEJ-XZWHSSHBSA-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

• 作为反应物：
  描述：

  2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl] 生成 (2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
  参考文献：
  名称：

  BALLENEGGER, M. E.;RIMBAULT, C. G.;ALBERT, A. I.;WEITH, A. J.;COURBAT, P.+

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 儿茶提取物 在 N,O-双(三甲基硅烷基)三氟乙酰胺 作用下， 以 乙腈 为溶剂， 生成 2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl]
  参考文献：
  名称：

  Unusual amount of (−)-mesquitol from the heartwood of Prosopis juliflora

  摘要：

  A large amount of flavonoid has been extracted and isolated from the heartwood of Prosopis juliflora, an exogenous wood species of Kenya. Structural and physicochemical elucidation based on FTIR, 1H and 13C NMR, GC-MS and HPLC analysis clearly demonstrated the presence of (-)-mesquitol as the sole compound without any noticeable impurities. The product was able to slow down oxidation of methyl linoleate induced by AIBN. The important amount and high purity of (-)-mesquitol present in the acetonic extract of P. juliflora could therefore be of valuable interest as a potential source of antioxidants from a renewable origin.

  DOI：

  10.1080/14786410801940968

文献信息

• Synthesis of condensed tannins. Part 3. Chemical shifts for determining the 6- and 8-bonding positions of ‘terminal of’(+)-catechin units
  作者：Hans K. L. Hundt、David G. Roux

  DOI：10.1039/p19810001227

  日期：——

  Pairs of 8- and 6-functionalized (Br, OH, OAc, CO2Me, and CH2Me groups) 3′,4′,5,7-tetra-O-methyl-(+)-catechins available through selective bromination and debromination reactions and hence via lithio-analogues, provide diagnostic chemical shifts of their residual 6- and 8-protons. These fall within narrow ranges [δ(CDCl3) 6.07–6.24 and 6.30–6.47 respectively] devoid of overlap, which are useful for

  通过选择性溴化可获得成对的8和6-官能化（Br，OH，OAc，CO 2 Me和CH 2 Me基）3'，4'，5,7-四-O-甲基-（+）-儿茶素脱溴反应，并因此通过硫代类似物，提供了其残留的6和8质子的诊断化学位移。它们落在狭窄的范围内[δ（CDCl 3）分别为6.07-6.24和6.30-6.47]，没有重叠，这对于区分4，6-和4，8-连接的双黄酮类化合物是有用的。还提供补充的1个H位移参数。
• 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.
• Henglein; Kraemer, Chemische Berichte, 1959, vol. 92, p. 2585,2589, 2591
  作者：Henglein、Kraemer

  DOI：——

  日期：——
• Unusual amount of (−)-mesquitol from the heartwood of <i>Prosopis juliflora</i>
  作者：Peter Sirmah、Stéphane Dumarçay、Eric Masson、Philippe Gérardin

  DOI：10.1080/14786410801940968

  日期：2009.1.20

  A large amount of flavonoid has been extracted and isolated from the heartwood of Prosopis juliflora, an exogenous wood species of Kenya. Structural and physicochemical elucidation based on FTIR, 1H and 13C NMR, GC-MS and HPLC analysis clearly demonstrated the presence of (-)-mesquitol as the sole compound without any noticeable impurities. The product was able to slow down oxidation of methyl linoleate induced by AIBN. The important amount and high purity of (-)-mesquitol present in the acetonic extract of P. juliflora could therefore be of valuable interest as a potential source of antioxidants from a renewable origin.
• BALLENEGGER, M. E.;RIMBAULT, C. G.;ALBERT, A. I.;WEITH, A. J.;COURBAT, P.+
  作者：BALLENEGGER, M. E.、RIMBAULT, C. G.、ALBERT, A. I.、WEITH, A. J.、COURBAT, P.+

  DOI：——

  日期：——