3,3-ethylenedioxy-4,7α,11βH-eudesm-5-en-6,13-olide | 202583-41-3

• 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: 3,3-ethylenedioxy-4,7α,11βH-eudesm-5-en-6,13-olide
• 英文别名: (3'S,3'aS,5'aS,9'R)-3',5'a,9'-trimethylspiro[1,3-dioxolane-2,8'-3a,4,5,6,7,9-hexahydro-3H-benzo[g][1]benzofuran]-2'-one
• CAS: 202583-41-3
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: BYNWXJFOMYHOAC-BUWBCJGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-4,7α,11βH-eudesm-5-en-6,13-olide 在 lithium aluminium tetrahydride 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (1'R,4'aS,8'S,8'aR)-7'-[2-Hydroxy-1-methyl-eth-(Z)-ylidene]-1',4'a-dimethyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-8',8'a-diol
  参考文献：
  名称：

  构建天然存在的二氢金呋喃呋喃倍半萜骨架的新方法

  摘要：

  通过桑顿宁的一系列转化，已经开发了一种普遍有效的合成广泛存在于Celastraceae植物家族中的二氢呋喃倍半萜的方法。密钥素材和通用步骤涉及战略酸催化双键移位得到6，的新碱促进环氧化物的重排7个生成两个关键功能（该C5OH和Δ 7,11双键）和立体选择性施工在不特别控制C7的立体化学的情况下制备四氢呋喃部分。特别地，该方法可在许多天然二氢agarofuran倍半萜烯的合成所需的位置引入任何数量的羟基。

  DOI：

  10.1016/s0040-4039(01)02203-1
• 作为产物：
  描述：

  山道年 在 Renay Ni 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 生成 3,3-ethylenedioxy-4,7α,11βH-eudesm-5-en-6,13-olide
  参考文献：
  名称：

  A general synthetic route of dihydroagarofuran sesquiterpenoid from α-(−)-santonin

  摘要：

  A general and efficient approach for synthesis of dihydroagarofuran sesquiterpenoid, the core structure of the polyol esters extensively present in the Celastraceae plants, has been developed by a series of transformations, which mainly include three creative and synthetically valuable conversions: the strategic double-bond shifting of 3, the versatile rearrangement of epoxide 5 generating two key functions, the C5-OH and 7,11-Double-bond, and the stereoselective cyclization/reduction of 8 constructing the tetrahydrofuran ring of 11. Thus the sesquiterpenoid 3 alpha,6 alpha,12-trihydroxy-dihydoagarofuran 1 was synthesized. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01766-3

文献信息

• A novel rearrangement of eudesmanolide enol ester epoxide: facile 1-step construction of the salvialane sesquiterpene skeleton
  作者：Wu Jiong Xia、De Run Li、Lei Shi、Yong Qiang Tu

  DOI：10.1016/s0957-4166(01)00255-5

  日期：2001.6

  A novel carbon–carbon rearrangement for the eudesmanolide sesquiterpene enol ester epoxide in the presence of a catalytic amount of Lewis acids (3–10 mol%) or an excess of NaOMe is disclosed. This reaction was developed to give a facile, one-step procedure for the construction of naturally occurring and bioactive salvialane sesquiterpenes. The reaction conditions were investigated extensively and a

  公开了在催化量的路易斯酸（3-10 mol％）或过量的NaOMe存在下，对马氏倍半萜烯倍半萜烯烯醇酯环氧化物的新型碳-碳重排。开发该反应可为构建天然存在且具有生物活性的丹参烷倍半萜烯提供简便，一步式的程序。对反应条件进行了广泛的研究，并讨论了可能的反应机理。
• Sun, Liangdong; Tu, Yongqiang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 9, p. 723 - 725
  作者：Sun, Liangdong、Tu, Yongqiang

  DOI：——

  日期：——
• A general synthetic route of dihydroagarofuran sesquiterpenoid from α-(−)-santonin
  作者：Yong Qiang Tu、Liang Dong Sun

  DOI：10.1016/s0040-4039(98)01766-3

  日期：1998.10

  A general and efficient approach for synthesis of dihydroagarofuran sesquiterpenoid, the core structure of the polyol esters extensively present in the Celastraceae plants, has been developed by a series of transformations, which mainly include three creative and synthetically valuable conversions: the strategic double-bond shifting of 3, the versatile rearrangement of epoxide 5 generating two key functions, the C5-OH and 7,11-Double-bond, and the stereoselective cyclization/reduction of 8 constructing the tetrahydrofuran ring of 11. Thus the sesquiterpenoid 3 alpha,6 alpha,12-trihydroxy-dihydoagarofuran 1 was synthesized. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A novel approach for construction of the naturally occurring dihydroagarofuran sesquiterpene skeleton
  作者：Wu Jiong Xia、De Run Li、Lei Shi、Yong Qiang Tu

  DOI：10.1016/s0040-4039(01)02203-1

  日期：2002.1

  dihydrofuran sesquiterpenes extensively present in the Celastraceae family of plants has been developed by a series of transformations from santonin. The key creative and versatile steps involve the strategic acid-catalyzed double-bond shifting affording 6, the novel base-promoted epoxide rearrangement of 7 generating two key functions (the C5OH and the Δ7,11 double bond) and the stereoselective construction

  通过桑顿宁的一系列转化，已经开发了一种普遍有效的合成广泛存在于Celastraceae植物家族中的二氢呋喃倍半萜的方法。密钥素材和通用步骤涉及战略酸催化双键移位得到6，的新碱促进环氧化物的重排7个生成两个关键功能（该C5OH和Δ 7,11双键）和立体选择性施工在不特别控制C7的立体化学的情况下制备四氢呋喃部分。特别地，该方法可在许多天然二氢agarofuran倍半萜烯的合成所需的位置引入任何数量的羟基。