Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester | 603095-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester
• 英文别名: [(3R)-6-methyl-3-(3-methyl-4-phenylmethoxyphenyl)hept-5-enyl] acetate
• CAS: 603095-32-5
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: FZNZILLCDRSLPH-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester 在 palladium on activated charcoal AD-mix-β 、 氢气 、 pyridinium hydrobromide perbromide 作用下， 反应 5.0h， 生成 Acetic acid (S)-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
• 作为产物：
  描述：

  3-(4-Benzyloxy-3-methyl-phenyl)-pentanedioic acid dimethyl ester 在 吡啶 、 咪唑 、 甲醇 、 sodium tetrahydroborate 、 锂硼氢 、 正丁基锂 、 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 四丁基氟化铵 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二甲基亚砜 、 三乙胺 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 生成 Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl 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.