8,14-seco-oleana-8(26),13-dien-3β-ol | 663615-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,14-seco-oleana-8(26),13-dien-3β-ol
• 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-ol
• CAS: 663615-98-3
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: LWFMCFZBFIZKKX-NBANTFJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8,14-seco-oleana-8(26),13-dien-3β-ol 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 8,14-seco-oleana-8(26),13-dien-3-one
  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：

  8,14-seco-oleana-8(26),13-dien-3β-ol acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.12h， 以89%的产率得到8,14-seco-oleana-8(26),13-dien-3β-ol
  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

• Total Synthesis of (+)-<i>seco</i>-C-Oleanane via Stepwise Controlled Radical Cascade Cyclization
  作者：Victoriano Domingo、Jesús F. Arteaga、José Luis López Pérez、Rafael Peláez、José F. Quı́lez del Moral、Alejandro F. Barrero

  DOI：10.1021/jo201968t

  日期：2012.1.6

  of the (+)-seco-C-oleanane 1 was accomplished. The successful route to this natural product involves as the key step a stepwise regio- and stereocontrolled catalytic radical polyene cascade cyclization from preoleanatetraene oxide (16), a process mediated by Cp2TiCl. The use of this single-electron-transfer complex permits mild cyclization conditions without using unnecessary prefunctionalizations and

  完成了（+）-癸基-C-油烷1的不对称简明全合成。通往这种天然产物的成功途径包括关键步骤，即由C12 Pc 2 TiCl介导的由预油萘四烯氧化物（16）进行的区域和立体控制的催化自由基多烯级联环化反应。这种单电子转移配合物的使用允许温和的环化条件，而无需使用不必要的预官能化，并在双环水平上停止了该过程。理论数据表明，第三环闭合具有很高的活化能，这将说明环化作用的控制。此过程还导致天然（-）-山茱ach醇B，山茶酚A和（+）-山梨醇-β-amyrin为次要化合物。
• 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.