(4S,4aR,8aS)-4-((E)-2-(furan-3-yl)vinyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexa hydronaphthalen-(4H)-one | 919103-33-6

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S,4aR,8aS)-4-((E)-2-(furan-3-yl)vinyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexa hydronaphthalen-(4H)-one
• 英文别名: hedychenone；(4S,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
• CAS: 919103-33-6
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: MXTCKNHXBBXULO-ZJDHVTHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,4aR,8aS)-4-((E)-2-(furan-3-yl)vinyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexa hydronaphthalen-(4H)-one 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以94%的产率得到yunnacoronarin D
  参考文献：
  名称：

  Synthesis, cytotoxic activity and structure–activity relationships of hedychenone analogues

  摘要：

  Hedychenone, a plant-derived labdane diterpenoid, showed potent in vitro cytotoxic activity against cancerous cells. In the present study, a series of analogues have been synthesized by modi. cation of the furanoid ring, double bond and the vinylic methyl functionality of this natural product lead and evaluated for their cytotoxic activities against human cancer cell lines. The structures of the target compounds were established by IR, H-1 NMR and mass spectral analysis. Majority of the analogues displayed potent activity than the parent compound, hedychenone. Preliminary structure-activity relationship studies indicated that furanoid ring has a greater impact on cytotoxicity than that of the decalone nucleus. However, dimerization through C-8 significantly enhanced the cytotoxic activity of the hedychenone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.101
• 作为产物：
  描述：

  ((1S,4S,4aS,8aR)-5,5,8a-Trimethyl-2-methylene-4-triethylsilanyloxy-decahydro-naphthalen-1-yl)-acetaldehyde 在 2,6-二甲基吡啶 、 sodium methylate 、 溶剂黄146 、 甲基磺酰氯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 25.0h， 生成 (4S,4aR,8aS)-4-((E)-2-(furan-3-yl)vinyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexa hydronaphthalen-(4H)-one
  参考文献：
  名称：

  Synthesis of hedychenone, yunnancoronarins and aframodial derivatives

  摘要：

  Starting with larixol, syntheses of furan and 1,4-enedial labdane-type diterpenes are presented, which has enabled a preparation of hedychenone (20% yield). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.053

文献信息

• Total Synthesis of (±)-Hedychenone:  Trimethyldecalin Terpene Systems via Stepwise Allenoate Diene Cycloaddition
  作者：Michael E. Jung、Masayuki Murakami

  DOI：10.1021/ol062456c

  日期：2006.12.1

  The total synthesis of hedychenone 1 is described. The cycloaddition of the hindered diene 2 and the allenecarboxylate 3 has been shown conclusively to proceed via the [2+2] cycloadduct 5 to give a 2:1 mixture of the desired formal Diels-Alder adducts, the exo and endo isomers 4xn and is thus a stepwise [4+2] cycloaddition. The exo isomer 4x was converted in four steps (reduction, oxidation, olefination

  描述了十七烯酮1的全合成。已证明受阻二烯2和烯丙基羧酸酯3的环加成通过[2 + 2]环加合物5最终进行，得到所需的正式Diels-Alder加合物，外向异构体和内向异构体4xn的2：1混合物，且因此逐步[4 + 2]环加成。exo异构体4x通过四个步骤（还原，氧化，烯化和去甲硅烷基化）转化为海藻酮1。