(-)-(5S,6R,8S,9S,10R,12R,14R)-6-acetoxy-12-hydroxycass-Δ¹³⁽¹⁵⁾-en-12,16-olide | 1132772-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (-)-(5S,6R,8S,9S,10R,12R,14R)-6-acetoxy-12-hydroxycass-Δ¹³⁽¹⁵⁾-en-12,16-olide
• 英文别名: 6β-acetoxy-12α-hydroxycassa-(13)15-en-16,12-olide；caesalpinolide-E；[(4aS,5R,6aS,7R,10aR,11aS,11bR)-10a-hydroxy-4,4,7,11b-tetramethyl-9-oxo-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-5-yl] acetate
• CAS: 1132772-46-3
• 化学式: C₂₂H₃₂O₅
• 分子量: 376.493
• InChiKey: SBMJOOYWCLPOPY-QQOBHIEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(5S,6R,8S,9S,10R,12R,14R)-6-acetoxy-12-hydroxycass-Δ¹³⁽¹⁵⁾-en-12,16-olide 、 乙酸酐 在 吡啶 作用下， 以1.0 mg的产率得到(-)-(5S,6R,8S,9S,10R,12R,14R)-6,12-diacetoxycass-Δ¹³⁽¹⁵⁾-en-12,16-olide
  参考文献：
  名称：

  Cassane Diterpenes from Caesalpinia bonduc

  摘要：

  Three cassane diterpene hemiketals, caesalpinolide-C, caesalpinolide-D, caesalpinolide-E and one cassane furanoditerpene were isolated from Caesalpinia bonduc. The molecular structures were elucidated using NMR spectroscopy in combination with IR, UV and mass spectral data and relative stereochemistries were determined through ROESY correlation. The isolated compounds were tested for their antiproliferative activity against MCF-7 (breast adenocarcinoma), DU145 (prostate carcinoma), C33A (Cervical carcinoma) and Vero (African green monkey kidney fibroblast) cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.12.008
• 作为产物：
  描述：

  (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane 在 间氯过氧苯甲酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以75%的产率得到(-)-(5S,6R,8S,9S,10R,12R,14R)-6-acetoxy-12-hydroxycass-Δ¹³⁽¹⁵⁾-en-12,16-olide
  参考文献：
  名称：

  Preparation and Cytotoxic Evaluation of Vouacapane Oxidation Products

  摘要：

  Treatment of (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane (1) with DDQ, mCPBA, or Cr(VI) reagents afforded diterpenoids with various degrees of oxidation at the furan and C rings. Oxidation of 1 using DDQ provided the known benzofuran 2, together with the new derivatives dimer 3, lactone 4, and aldehyde 5, while mCPBA oxidation gave 2, spirocassenolide 6, and cassenolides 7 and 8a. Oxidation of 1 with CrO3 gave 4, 6, 8a, and spirocassenolide 9, while the use of K2Cr2O7 yielded 4, 9, and spirocassenolide 10. The structures of the new compounds followed from HRMS, NMR measurements, and by single-crystal X-ray diffraction of 3, 4, 8b, and 10. Compounds 1, 2, and 6 were evaluated for their cytotoxic activity against the MCF-7 and HL-60 cancer cells, showing moderate cytotoxic activity.

  DOI：

  10.3987/com-19-14195