7α,8α-isopropylidenedioxy-11-acetoxydrim-2-ene | 186451-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7α,8α-isopropylidenedioxy-11-acetoxydrim-2-ene
• 英文别名: [(3aR,4aS,8aS,9S,9aS)-2,2,5,5,8a,9a-hexamethyl-4,4a,8,9-tetrahydro-3aH-naphtho[2,3-d][1,3]dioxol-9-yl]methyl acetate
• CAS: 186451-72-9
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: QDZZKIORSLOIOM-ZOTMLPGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7α,8α-isopropylidenedioxy-11-acetoxydrim-2-ene 在 platinum(IV) oxide 吡啶-N-氧化物 、 selenium(IV) oxide 、 氢气 、 乙酸酐 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 乙腈 为溶剂， 反应 86.5h， 生成 1α,11-diacetoxy-drim-7-ene
  参考文献：
  名称：

  Microbiologically-assisted hemisynthesis of 1α-hydroxydrimenol

  摘要：

  The hemisynthesis of 1 alpha -hydroxydrimenol has been selected to illustrate a synthetic route involving an initial microbial 3 beta -hydroxylation of a drimenol derivative followed by a functionalization transfer to position 1 alpha, thus generating a new potentially bioactive hydroxylated terpenic compound, Several methods have been investigated for the protection and the regeneration of the 7,8-double bond of drimenyl derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00353-6
• 作为产物：
  描述：

  3β-hydroxy-7α,8α-isopropylidenedioxy-11-acetoxydrimane 在 三苯基膦 、 偶氮二甲酸二乙酯 、 对甲苯磺酸钠 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以87%的产率得到7α,8α-isopropylidenedioxy-11-acetoxydrim-2-ene
  参考文献：
  名称：

  Microbiologically-assisted hemisynthesis of 1α-hydroxydrimenol

  摘要：

  The hemisynthesis of 1 alpha -hydroxydrimenol has been selected to illustrate a synthetic route involving an initial microbial 3 beta -hydroxylation of a drimenol derivative followed by a functionalization transfer to position 1 alpha, thus generating a new potentially bioactive hydroxylated terpenic compound, Several methods have been investigated for the protection and the regeneration of the 7,8-double bond of drimenyl derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00353-6

文献信息

• Practical and Efficient 1α-Hydroxylation of 4,4-Dimethyl-2-Ene Derivatives in Terpenic Series
  作者：Gérard Aranda、Mireille Bertranne-Delahaye、Robert Azerad、Michèle Maurs、Manuel Cortés、Hector Ramirez、Gonzalo Vernal、Thierry Prangé

  DOI：10.1080/00397919708004804

  日期：1997.1.1

  The third part of a triptycal synthesis providing 1 alpha-hydroxy compounds, through microbial hydroxylation in position-3 of terpenoid substrates, followed by dehydration to 4,4-dimethyl-2-ene compounds and subsequent allylic hydroxylation by SeO2/pyridine N-oxide, is described.