ethyl 3-[2-(2-hydroxy-1,1-dimethylethoxy)-5-methoxy-4-methylphenyl]-4-pentenoate | 898538-92-6

• 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: ethyl 3-[2-(2-hydroxy-1,1-dimethylethoxy)-5-methoxy-4-methylphenyl]-4-pentenoate
• 英文别名: Ethyl 3-[2-(1-hydroxy-2-methylpropan-2-yl)oxy-5-methoxy-4-methylphenyl]pent-4-enoate
• CAS: 898538-92-6
• 化学式: C₁₉H₂₈O₅
• 分子量: 336.428
• InChiKey: GDFKNDZECMWFNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-[2-(2-hydroxy-1,1-dimethylethoxy)-5-methoxy-4-methylphenyl]-4-pentenoate 在 chromium(VI) oxide 、 sodium tetrahydroborate 、 硫酸 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 6.5h， 生成 O-methylheliannuol C
  参考文献：
  名称：

  The synthesis of heliannuol C, an allelochemical from Helianthus annuus

  摘要：

  The synthesis of the allelochemical heliannuol C I is described by employing a Bargellini condensation and a Claisen rearrangement to install the gem-dimethyl and vinyl functionalities, respectively. A Dieckmann cyclisation of diester 11 enabled the generation of the benzoxepane ring system enshrined in 1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.011
• 作为产物：
  描述：

  6-hydroxy-7-methyl-2H-chromen-2-one 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium carbonate 、 丙酸 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 23.0h， 生成 ethyl 3-[2-(2-hydroxy-1,1-dimethylethoxy)-5-methoxy-4-methylphenyl]-4-pentenoate
  参考文献：
  名称：

  The synthesis of heliannuol C, an allelochemical from Helianthus annuus

  摘要：

  The synthesis of the allelochemical heliannuol C I is described by employing a Bargellini condensation and a Claisen rearrangement to install the gem-dimethyl and vinyl functionalities, respectively. A Dieckmann cyclisation of diester 11 enabled the generation of the benzoxepane ring system enshrined in 1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.011

文献信息

• Bargellini condensation of coumarins. Expeditious route to o-carboxyvinylphenoxyisobutyric acids and application to the synthesis of sesquiterpenes helianane, heliannuol A and heliannuol C
  作者：Bidyut Biswas、Prabir K. Sen、Ramanathapuram V. Venkateswaran

  DOI：10.1016/j.tet.2007.09.006

  日期：2007.11

  The direct Bargellini condensation of coumarins involving reaction with chloroform and acetone in the presence of aqueous sodium hydroxide furnished o-carboxyvinylphenoxyisobutyric acids in good yields. The utility of this new useful protocol was demonstrated by the transformation of the three diesters 9b, 9f and 9g to the sesquiterpenes helianane 4, heliannuol A 2 and heliannuol C 3, respectively

  香豆素的Bargellini直接缩合反应涉及在氢氧化钠水溶液存在下与氯仿和丙酮反应，从而以良好的收率提供了邻羧基羧乙烯基苯氧基异丁酸。通过将三个二酯9b，9f和9g分别转化为倍半萜烯helaneane 4，heliannuol A 2和heliannuol C 3，证明了该新有用方案的实用性。
• The synthesis of heliannuol C, an allelochemical from Helianthus annuus
  作者：Bidyut Biswas、Prabir K. Sen、Ramanathapuram V. Venkateswaran

  DOI：10.1016/j.tetlet.2006.04.011

  日期：2006.6

  The synthesis of the allelochemical heliannuol C I is described by employing a Bargellini condensation and a Claisen rearrangement to install the gem-dimethyl and vinyl functionalities, respectively. A Dieckmann cyclisation of diester 11 enabled the generation of the benzoxepane ring system enshrined in 1. (c) 2006 Elsevier Ltd. All rights reserved.