(4S,5R)-4-hydroxy-5-vinyl-2-cyclohexen-1-one | 189942-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-4-hydroxy-5-vinyl-2-cyclohexen-1-one
• 英文别名: (4R,5S)-5-ethenyl-4-hydroxycyclohex-2-en-1-one
• CAS: 189942-88-9
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: ADMWCXTVMLKIGR-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-hydroxy-5-vinyl-2-cyclohexen-1-one 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 苄基三甲基氢氧化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 异辛烷 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 (1S,2S,4S,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4-ethenyl-7-oxabicyclo[4.1.0]heptan-2-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Eutypoxide B

  摘要：

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.

  DOI：

  10.1021/jo9617326
• 作为产物：
  描述：

  (3aR,7S,7aS)-7-ethenyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-5-one 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R)-4-hydroxy-5-vinyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Eutypoxide B

  摘要：

  The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa Lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from D-(-)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.

  DOI：

  10.1021/jo9617326

文献信息

• POLYCYCLIC CARBOGENIC MOLECULES AND USES THEREOF AS ANTI-CANCER AGENTS
  申请人：Northwestern University

  公开号：US20190127306A1

  公开（公告）日：2019-05-02

  Disclosed are new polycyclic carbogenic molecules and their methods of synthesis. The new polycyclic carbogenic molecules may be utilized in anti-cancer therapies. In particular, the polycyclic carbogenic molecules may be formulated as pharmaceutical compositions that comprise the small molecules, which compositions may be administered in methods of treating and/or preventing cell proliferative diseases and disorders such as cancer. The new polycyclic carbogenic molecules may be prepared from vinyl- or allyl-substituted cyclohexenone precursors via preparation of a silyl bis-enol ether intermediate.

  揭示了新的多环碳基分子及其合成方法。这些新的多环碳基分子可以用于抗癌疗法。特别是，这些多环碳基分子可以制成包含小分子的药物组合物，这些组合物可以在治疗和/或预防细胞增殖性疾病和癌症等疾病的方法中使用。这些新的多环碳基分子可以通过从乙烯或烯丙基取代的环己酮前体制备硅烷双烯醚中间体来制备。
• A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules
  作者：Emily E. Robinson、Regan J. Thomson

  DOI：10.1021/jacs.7b13234

  日期：2018.2.7

  The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic

  环酮通过甲硅烷基双烯醇醚的立体选择性氧化偶联，然后是闭环复分解，是从简单的前体制备多种多环支架的通用且强大的反应序列。模块化策略成功地构建了在众多生物活性天然产物家族中普遍存在的子结构，这些子结构的取代基和碳环组成各不相同。几种制备的化合物显示出对一组肿瘤细胞系具有有效的细胞毒活性。复杂的抗疟海洋二萜 (+)-7,20-二异氰基二萜的简洁且高度收敛的 17 步正式合成进一步证明了该策略的实用性。