5-[1,3]Dioxolan-2-yl-3-(4-methoxy-3-methyl-phenyl)-3-methyl-pentanoic acid methyl ester | 309751-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[1,3]Dioxolan-2-yl-3-(4-methoxy-3-methyl-phenyl)-3-methyl-pentanoic acid methyl ester
• 英文别名: Methyl 5-(1,3-dioxolan-2-yl)-3-(4-methoxy-3-methylphenyl)-3-methylpentanoate
• CAS: 309751-07-3
• 化学式: C₁₈H₂₆O₅
• 分子量: 322.401
• InChiKey: JGEDKOIVAVIXRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[1,3]Dioxolan-2-yl-3-(4-methoxy-3-methyl-phenyl)-3-methyl-pentanoic acid methyl ester 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 6-Hydroxy-3-(4-methoxy-3-methyl-phenyl)-3-methyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective total syntheses of (±)-1,14-herbertenediol and (±)-tochuinyl acetate and facile total syntheses of (±)-α-herbertenol, (±)-β-herbertenol and (±)-1,4-cuparenediol

  摘要：

  Stereoselective total syntheses of (+/-)-1,14-herbertenediol (7) and (+/-)-tochuinyl acetate (10) and facile total syntheses of (+/-)-a=alpha-herbertenol (2), (+/-)-beta-herbertenol (3) and (+/-)-1,4-cuparenediol (8) have been successfully accomplished involving intramolecular cyclisation of 3-aryl-3-methyl-6-bromohexanoates and in situ methylation of the resulting cyclopentanecarboxylates as the key reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02674-6
• 作为产物：
  描述：

  (2-(1,3-dioxolan-2-yl)ethyl)magnesium bromide 在 氢氧化钾 、 copper(I) bromide dimethylsulfide complex 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙二醇 为溶剂， 生成 5-[1,3]Dioxolan-2-yl-3-(4-methoxy-3-methyl-phenyl)-3-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective total syntheses of (±)-1,14-herbertenediol and (±)-tochuinyl acetate and facile total syntheses of (±)-α-herbertenol, (±)-β-herbertenol and (±)-1,4-cuparenediol

  摘要：

  Stereoselective total syntheses of (+/-)-1,14-herbertenediol (7) and (+/-)-tochuinyl acetate (10) and facile total syntheses of (+/-)-a=alpha-herbertenol (2), (+/-)-beta-herbertenol (3) and (+/-)-1,4-cuparenediol (8) have been successfully accomplished involving intramolecular cyclisation of 3-aryl-3-methyl-6-bromohexanoates and in situ methylation of the resulting cyclopentanecarboxylates as the key reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02674-6

文献信息

• New total synthesis of (±)-herbertene, (±)-β-herbertenol and (±)-herbertenediol
  作者：Pranab Dutta Gupta、Ashutosh Pal、Arnab Roy、Debabrata Mukherjee

  DOI：10.1016/s0040-4039(00)01298-3

  日期：2000.9

  The total syntheses of the herbertane sesquiterpenes (±)-herbertene (1), (±)-β-herbertenol (2) and (±)-herbertenediol (5) have been successfully accomplished involving copper-catalysed conjugate addition of Grignard reagents to unsaturated compounds and α,α-dimethylation of primary esters as key reactions.

  赫伯坦倍半萜烯（±）-香波烯（1），（±）-β-香波烯醇（2）和（±）-香波烯二醇（5）的总合成已成功完成，其中涉及将铜催化剂与格氏试剂共轭加成到不饱和化合物和伯酯的α，α-二甲基化反应为关键反应。