8,14-seco-oleana-8(26),13-dien-3β-ol acetate | 663616-00-0

• 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: 8,14-seco-oleana-8(26),13-dien-3β-ol acetate
• 英文别名: [(2S,4aR,5S,8aR)-5-[2-[(4aR,8aR)-2,4a,7,7-tetramethyl-3,4,5,6,8,8a-hexahydronaphthalen-1-yl]ethyl]-1,1,4a-trimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-2-yl] acetate
• CAS: 663616-00-0
• 化学式: C₃₂H₅₂O₂
• 分子量: 468.764
• InChiKey: MEAUGBBALJFYPA-SGBLTFEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8,14-seco-oleana-8(26),13-dien-3β-ol acetate 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.29h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2S,4aR,5S,8aR)-1,1,4a-trimethyl-6-methylene-5-[2-((4aR,8aR)-2,4a,7,7-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-decahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  First seco-C Oleananes from Nature

  摘要：

  [GRAPHICS]The triterpenes 8,14-seco-oleana-8(26),13-dien-3beta-ol (1) and its acetyl derivative 2 were isolated from Stevia viscida and Stevia eupatoria, respectively. Their structures were elucidated by 2D NMR, including carbon-carbon connectivity experiments, and confirmed by X-ray diffraction analysis of ketone 3. The absolute configuration was determined by NMR analysis of the Mosher esters of 1. The biogenetic implications of the new substances are discussed.

  DOI：

  10.1021/ol036107j
• 作为产物：
  描述：

  乙酸酐 、 8,14-seco-oleana-8(26),13-dien-3β-ol 在 吡啶 作用下， 反应 24.0h， 以91%的产率得到8,14-seco-oleana-8(26),13-dien-3β-ol acetate
  参考文献：
  名称：

  First seco-C Oleananes from Nature

  摘要：

  [GRAPHICS]The triterpenes 8,14-seco-oleana-8(26),13-dien-3beta-ol (1) and its acetyl derivative 2 were isolated from Stevia viscida and Stevia eupatoria, respectively. Their structures were elucidated by 2D NMR, including carbon-carbon connectivity experiments, and confirmed by X-ray diffraction analysis of ketone 3. The absolute configuration was determined by NMR analysis of the Mosher esters of 1. The biogenetic implications of the new substances are discussed.

  DOI：

  10.1021/ol036107j

文献信息

• First <i>seco</i>-C Oleananes from Nature
  作者：Luisa U. Román、Diana Guerra-Ramírez、Gerardo Morán、Iván Martínez、Juan D. Hernández、Carlos M. Cerda-García-Rojas、J. Martín Torres-Valencia、Pedro Joseph-Nathan

  DOI：10.1021/ol036107j

  日期：2004.1.1

  [GRAPHICS]The triterpenes 8,14-seco-oleana-8(26),13-dien-3beta-ol (1) and its acetyl derivative 2 were isolated from Stevia viscida and Stevia eupatoria, respectively. Their structures were elucidated by 2D NMR, including carbon-carbon connectivity experiments, and confirmed by X-ray diffraction analysis of ketone 3. The absolute configuration was determined by NMR analysis of the Mosher esters of 1. The biogenetic implications of the new substances are discussed.