4-hydroxy-3,3-dimethyl-5-(2,2,3-trimethaneylcyclopent-3-en-1-yl)pentan-2-one | 686776-48-7

• 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: 4-hydroxy-3,3-dimethyl-5-(2,2,3-trimethaneylcyclopent-3-en-1-yl)pentan-2-one
• 英文别名: 4-hydroxy-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-ene-1-yl)pentan-2-one；4-hydroxy-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-one；4-Hydroxy-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-on；3,3-dimethyl-4-hydroxy-5-(2,2,3-trimethyl-3-cyclopentenyl)-pentan-2-one
• CAS: 686776-48-7
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: ONECILGFBWGHTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3,3-dimethyl-5-(2,2,3-trimethaneylcyclopent-3-en-1-yl)pentan-2-one 在 吡啶 、 甲基磺酰氯 、 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到3,3-dimethyl-5-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-pent-4-en-2-one
  参考文献：
  名称：

  Synthesis of Polysantol® and related sandalwood-type odorants using magnesium α-bromoketone enolates

  摘要：

  The syntheses of the commercial sandalwood-type odorant Polysantol((R)) and several structurally related compounds are described. The methodology followed is based on a selective and efficient magnesium-mediated aldol reaction of the starting material, alpha-campholenic aldehyde and different alpha-bromoketones. Dehydration of the resulting secondary alcohol and reduction of the carbonyl group allowed the completion of the syntheses of the target molecules in 30-56% overall yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.142
• 作为产物：
  描述：

  3-甲基-2-丁酮 在 溴 、 magnesium 、 溶剂黄146 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 0.17h， 生成 4-hydroxy-3,3-dimethyl-5-(2,2,3-trimethaneylcyclopent-3-en-1-yl)pentan-2-one
  参考文献：
  名称：

  Synthesis of Polysantol® and related sandalwood-type odorants using magnesium α-bromoketone enolates

  摘要：

  The syntheses of the commercial sandalwood-type odorant Polysantol((R)) and several structurally related compounds are described. The methodology followed is based on a selective and efficient magnesium-mediated aldol reaction of the starting material, alpha-campholenic aldehyde and different alpha-bromoketones. Dehydration of the resulting secondary alcohol and reduction of the carbonyl group allowed the completion of the syntheses of the target molecules in 30-56% overall yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.142

文献信息

• [EN] PROCESS FOR THE PREPARATION OF POLYSANTOL-TYPE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DE TYPE POLYSANTOL
  申请人：FIRMENICH & CIE

  公开号：WO2017207707A1

  公开（公告）日：2017-12-07

  The present invention relates to the field of organic synthesis and more specifically it concerns a novel compound of formula (I) which could be used as a novel intermediate in the process for the preparation of compound of formula (III).

  本发明涉及有机合成领域，更具体地涉及一种新的化合物(I)，其可用作制备化合物(III)的新中间体。
• Process for the preparation of polysantol-type compounds
  申请人：Firmenich SA

  公开号：US10807941B2

  公开（公告）日：2020-10-20

  The present invention relates to the field of organic synthesis and more specifically it concerns a novel compound of formula (I). The invention additionally relates to a process for preparing a compound of formula (III) using the compound of formula (I) as an intermediate, wherein the process involves elimination of the R3(X)nC(═O)O functional group of the compound of formula (I).

  本发明涉及有机合成领域，更具体地说，它涉及一种新型的式 (I) 化合物。本发明还涉及一种以式（I）化合物为中间体制备式（III）化合物的工艺，其中该工艺涉及消除式（I）化合物的 R3(X)nC(═O)O 官能团。
• PROCESS FOR THE PREPARATION OF POLYSANTOL-TYPE COMPOUNDS
  申请人：Firmenich SA

  公开号：EP3464235A1

  公开（公告）日：2019-04-10