N-acetyltyramine 1-O-β-glucoside | 1233346-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyltyramine 1-O-β-glucoside
• 英文别名: N-[2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethyl]acetamide
• CAS: 1233346-09-2
• 化学式: C₁₆H₂₃NO₇
• 分子量: 341.361
• InChiKey: JVYCDFJBIOIPDL-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-acetyltyramine 1-O-β-glucoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  An Unusual Stress Metabolite Induced by CuCl₂ and Other Constituents from the Leaves of Chloranthus anhuiensis

  摘要：

  A 6-eremophilene derivative 2 with an unusual pendant was produced as phytoalexin in the fresh leaves of Chloranthus anhuiensis K. F. Wu in response to abiotic stress elicitation by CuCl2. The phytoalexin was characterized as a sesquiterpene with a (2,6-dimethoxy-4-hydroxy)benzyl moiety pendant. Two new sesquiterpenes, (3R,45,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid (1) and (3R,4S,5R,6R,8R,10S)-3,6,8-trihydroxy-7(11)-eremophilen-12,8-olide (3), one new sesquiterpene glycoside, anhuienoside A (4), one new caffeoyl phenylethanoid diglycoside with an unusual cyclic structure. anhuienoside B (5), and one new tyramine derivative, N-acetyltyramine 1-O-beta-D-glucoside (6). and three known compounds were also isolated. Their structures and relative configurations were established by spectroscopic means. The absolute configurations of 1-3 were defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra.

  DOI：

  10.1021/np100063q

文献信息

• An Unusual Stress Metabolite Induced by CuCl₂ and Other Constituents from the Leaves of <i>Chloranthus anhuiensis</i>
  作者：Bin Wu、Lishe Gan、Haibin Qu

  DOI：10.1021/np100063q

  日期：2010.6.25

  A 6-eremophilene derivative 2 with an unusual pendant was produced as phytoalexin in the fresh leaves of Chloranthus anhuiensis K. F. Wu in response to abiotic stress elicitation by CuCl2. The phytoalexin was characterized as a sesquiterpene with a (2,6-dimethoxy-4-hydroxy)benzyl moiety pendant. Two new sesquiterpenes, (3R,45,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid (1) and (3R,4S,5R,6R,8R,10S)-3,6,8-trihydroxy-7(11)-eremophilen-12,8-olide (3), one new sesquiterpene glycoside, anhuienoside A (4), one new caffeoyl phenylethanoid diglycoside with an unusual cyclic structure. anhuienoside B (5), and one new tyramine derivative, N-acetyltyramine 1-O-beta-D-glucoside (6). and three known compounds were also isolated. Their structures and relative configurations were established by spectroscopic means. The absolute configurations of 1-3 were defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra.