djalonenoside tetraacetate | 14312-74-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: djalonenoside tetraacetate
• 英文别名: peracetyl rigenolide F；sweroside tetraacetate；tetraacetylsweroside；peracetyl rigenolide G；(4aS)-6c-(tetra-O-acetyl-β-D-glucopyranosyloxy)-5t-vinyl-(4ar)-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one；(4aS)-6c-(Tetra-O-acetyl-β-D-glucopyranosyloxy)-5t-vinyl-(4ar)-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-on；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 14312-74-4
• 化学式: C₂₄H₃₀O₁₃
• 分子量: 526.494
• InChiKey: AGMGHAAGDJHFPJ-NBNRBSLVSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  618.3±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 djalonenoside tetraacetate 生成 Acetic acid (S)-2-acetoxy-1-[(3S,4S,4aS)-8-oxo-3-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4,4a,5,6-tetrahydro-3H,8H-pyrano[3,4-c]pyran-4-yl]-ethyl ester
  参考文献：
  名称：

  Bock,K. et al., Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry, 1976, vol. 30, p. 743 - 748

  摘要：

  DOI：
• 作为产物：
  描述：

  獐牙菜苷 生成 djalonenoside tetraacetate
  参考文献：
  名称：

  LIN, CHUN-NAN;CHUNG, MEI-ING;GAN, KIM-HONG;CHIANG, JEN-RON, PHYTOCHEMISTRY, 26,(1987) N 8, 2381-2384

  摘要：

  DOI：

文献信息

• Studies on Monoterpene Glucosides and Related Natural Products Part 51. Absolute Structures of Hydrangenosides A, B, C, D, E, F, and G. Novel Type Secoiridoid Glucosides from TwoHydrangea Plants
  作者：Shinichi Uesato、Yoshio Takeda、Toshihiro Hashimoto、Kenichi Uobe、Hiroyuki Inouye、Heihachiro Taguchi、Toru Endo

  DOI：10.1002/hlca.19840670812

  日期：1984.12.19

  From Hydrangea macrophylla var. Macrophylla, four new secoiridoid glucosides, hydrangenosies A, B, C and D, were isolated, along with the known iridoid glucosides loganin, secologanin, secologanic acid and sweroside. Moreover, hydrangenosides E, F, and G, the glucosides of the same class, were isolated together with hydrangenosides C and D from Hydrangea Scandens. Based on spectroscopic and chemical

  来自绣球花。分离了大叶菊，四种新的类蛇皮苷糖苷，绣球菌A，B，C和D，以及已知的鸢尾苷葡糖苷loganin，secologanin，secologanic acid和seroeroside。此外，hydrangenosides E，F，和G，同一类的糖苷，被一起从hydrangenosides C和d分离绣球藤。基于光谱和化学方法，阐明了新的葡糖苷的新结构，该葡糖苷由secologanin和a草酸-丙二酸酯衍生的单元组成，它们通过CC键连接。但是，对其他七种绣球花植物进行了测试，发现它们不包含八仙花苷型糖苷。
• Rigenolides D–H, norsecoiridoid and secoiridoids from Gentiana rigescens Franch
  作者：Yoshihiro Suyama、Naonobu Tanaka、Kazuyoshi Kawazoe、Kotaro Murakami、Shun-Lin Li、Han-Dong Sun、Yoshiki Kashiwada

  DOI：10.1007/s11418-018-1181-2

  日期：2018.3

  Five new compounds, rigenolides D–H (1–5), were isolated from the aerial parts of Gentiana rigescens Franch. Their structures were assigned by detailed spectroscopic analyses and chemical conversions. Rigenolides D (1) and E (2) were elucidated to be a secoiridoid and a norsecoiridoid, respectively, possessing a dienone moiety in common. Rigenolides F–H (3–5) were assigned as acylated secoiridoid glucosides

  五个新的化合物，rigenolides d-H（1 - 5），从地上部分分离龙胆rigescens獐。通过详细的光谱分析和化学转化确定了它们的结构。绞股蓝内酯D（1）和E（2）被阐明为分别具有二烯酮部分的secrididoid和norsecoiridoid。蓖麻油苷F–H（3 – 5）被指定为酰化的类蛇药苷糖苷。
• Monoterpene diol, iridoid glucoside and dibenzo-α-pyrone from Anthocleista djalonensis
  作者：Patricia A. Onocha、Dominic A. Okorie、Joseph D. Connolly、David S. Roycroft

  DOI：10.1016/0031-9422(95)00121-m

  日期：1995.11

  Anthocleista djalonensis has provided a new monoterpene diol, djalonenol, as well as the known iridoid glucoside djalonenoside (also sweroside). Also isolated for the first time from a plant source is a dibenzo-alpha-pyrone-djalonensone, previously identified as a fungal metabolite. The structure of the new compound was elucidated on the basis of its chemical and spectral data as tetrahydro-3-hydroxy hydroxymethylene-4-(3-hydroxymethylene prop-1-ene)-2H-pyran-2-one.
• Hamilton, Raymond G.; McLean, Stewart, Canadian Journal of Chemistry, 1981, vol. 59, p. 215 - 216
  作者：Hamilton, Raymond G.、McLean, Stewart

  DOI：——

  日期：——
• Purdy, John Richard; Hamilton, Raymond G.; Akhter, Lalarukh, Canadian Journal of Chemistry, 1981, vol. 59, p. 210 - 214
  作者：Purdy, John Richard、Hamilton, Raymond G.、Akhter, Lalarukh、McLean, Stewart

  DOI：——

  日期：——