methyl 16-(hydroxymethyl)lambertianate | 176692-86-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 16-(hydroxymethyl)lambertianate
• 英文别名: methyl 16-hydroxymethyllambertianate；methyl (1S,4aR,5S,8aR)-5-[2-[2-(hydroxymethyl)furan-3-yl]ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 176692-86-7
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: USJUZEYYTPWSSZ-GWWHBBDRSA-N

物化性质

• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 16-(hydroxymethyl)lambertianate 以 丙酮 为溶剂， 以0.27 g的产率得到(1R,2R,6S,7R,10S,12R,16S)-6-carboxymethyl-12-hydroxymethyl-2,6-dimethyl-13-oxapentacyclo<8.8.0.0^2,7.0^10,16.0^12,16>octadec-14-ene
  参考文献：
  名称：

  Vilsmeier?Haack reaction of methyl lambertianate and non-sensitized photocyclization of the resulting product

  摘要：

  Vilsmeier-Haack formylation of methyl lambertianate results in its 16-formyl derivative as the predominant product, which readily enters the intramolecular reaction of photochemical [2+2]-cycloaddition in the absence of a sensitizer.

  DOI：

  10.1007/bf00713615
• 作为产物：
  描述：

  lambertianic acid methyl ester 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 48.33h， 生成 methyl 16-(hydroxymethyl)lambertianate
  参考文献：
  名称：

  Vilsmeier?Haack reaction of methyl lambertianate and non-sensitized photocyclization of the resulting product

  摘要：

  Vilsmeier-Haack formylation of methyl lambertianate results in its 16-formyl derivative as the predominant product, which readily enters the intramolecular reaction of photochemical [2+2]-cycloaddition in the absence of a sensitizer.

  DOI：

  10.1007/bf00713615

文献信息

• Synthetic transformation of higher terpenoids 31. Synthesis of 1,2,3-triazolyl-containing furan labdanoids and studies of their cytotoxic activity
  作者：Yu. V. Kharitonov、E. E. Shul’ts、M. M. Shakirov、M. A. Pokrovskii、A. G. Pokrovskii、G. A. Tolstikov

  DOI：10.1007/s11172-013-0297-5

  日期：2013.9

  Abstract16-(1-R-1,2,3-Triazol-4-ylethyl)-, 16-(1-R-1,2,3-triazol-4-ylmethoxymethyl)-, and 16-2-(1-R-1,2,3-triazol-4-yl)-1-[(1-R-1,2,3-triazol-4-ylmethoxy)ethyl]}-substituted derivatives of methyl lambertianate were synthesized by 1,3-cycloaddition of labdanoid alkynes with azides. The compounds obtained possess considerable cytotoxicity toward the human tumor cell lines CEM-13, MT-4, and U-937. The

  摘要 16-(1-R-1,2,3-Triazol-4-ylethyl)-, 16-(1-R-1,2,3-triazol-4-ylmethoxymethyl)-, 和 16-2-(1 -R-1,2,3-三唑-4-基)-1-[(1-R-1,2,3-三唑-4-基甲氧基)乙基]}-取代的朗伯坦酸甲酯衍生物由1,劳丹醇炔烃与叠氮化物的 3-环加成反应。获得的化合物对人肿瘤细胞系 CEM-13、MT-4 和 U-937 具有相当大的细胞毒性。发现最活跃的化合物 16-(2-2-[(1-benzyl-1H-1,2,3-triazol-4-yl)acetyl]furan-3-yl}ethyl)lambertianate 可抑制在 7–12 μmol L−1 的浓度下，肿瘤细胞的活力增加了 50% (CCID50)。
• Chernov; Shul'ts; Shakirov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1455 - 1464
  作者：Chernov、Shul'ts、Shakirov、Tolstikov

  DOI：——

  日期：——
• Synthetic transformations of higher terpenoids: XXIX. Gold catalyzed cycloisomerization of propargylaminomethyl substituted and propargyloxymethyl substituted furanolabdanoids
  作者：Yu. V. Kharitonov、E. E. Shults、M. M. Shakirov、I. Yu. Bagryanskaya、G. A. Tolstikov

  DOI：10.1134/s1070428012080088

  日期：2012.8

  16-Propargylaminomethyl substituted and 16-propargyloxymethyl substituted furanolabdanoids were synthesized, which under the action of AuCl3 in acetonitrile underwent cycloisomerization forming 7-hydroxyisoindolines or 7-hydroxydihydroisobenzofurans substituted by a terpenoid fragment.