Acetic acid (R)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester | 603095-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Acetic acid (R)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester
• 英文别名: [(3R)-3-(3-bromo-4-hydroxy-5-methylphenyl)-5,6-dihydroxy-6-methylheptyl] acetate
• CAS: 603095-24-5
• 化学式: C₁₇H₂₅BrO₅
• 分子量: 389.286
• InChiKey: NRIHCHSTXAOPAQ-KEKZHRQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (R)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester 在 四丁基高氯酸铵 作用下， 以68%的产率得到Acetic acid 2-[(R)-7-bromo-2-(1-hydroxy-1-methyl-ethyl)-9-methyl-8-oxo-1-oxa-spiro[4.5]deca-6,9-dien-4-yl]-ethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

  摘要：

  Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms. by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01094-3
• 作为产物：
  描述：

  (S)-3-(4-Benzyloxy-3-methyl-phenyl)-4-((R)-1-phenyl-ethylcarbamoyl)-butyric acid methyl ester 在 palladium on activated charcoal 吡啶 、 AD-mix-α 、 锂硼氢 、 正丁基锂 、 camphor-10-sulfonic acid 、 氢气 、 二异丁基氢化铝 、 pyridinium hydrobromide perbromide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 苯 为溶剂， 反应 5.0h， 生成 Acetic acid (R)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester
  参考文献：
  名称：

  Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

  摘要：

  Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms. by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01094-3

文献信息

• Enantioselective synthesis of heliannuol E; structural consideration of natural molecule
  作者：Fuminao Doi、Takahisa Ogamino、Takeshi Sugai、Shigeru Nishiyama

  DOI：10.1016/s0040-4039(03)01094-3

  日期：2003.6

  Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms. by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position. (C) 2003 Elsevier Science Ltd. All rights reserved.