4-hydroxy-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)pentan-2-one | 686776-52-3

• 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-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)pentan-2-one
• 英文别名: 4-Hydroxy-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-one
• CAS: 686776-52-3
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: XRPWZZIQDPCKAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)pentan-2-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到trans-5-(2,2,3-Trimethyl-3-cyclopenten-1-yl)-3-penten-2-on
  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：

  2,2,3-三甲基-3-环戊烯-1-乙醛 、 3-溴-2-丁酮 在 magnesium 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以75%的产率得到4-hydroxy-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-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

• Process for making intermediates for fragrance components from α-campholenic aldehyde
  申请人：Millennium Specialty Chemicals, Inc.

  公开号：US07262329B1

  公开（公告）日：2007-08-28

  A two-step aldol condensation process is disclosed. α-Campholenic aldehyde (ACA) and methyl ethyl ketone (MEK) react in the presence of a base under conditions effective to produce a mixture comprising a high yield of ketol condensation products. Dehydration of the ketols in the presence of an organic sulfonic acid provides unsaturated ketones that are valuable intermediates for fragrance components for synthetic sandalwood products. Compared with the usual one-step, base-catalyzed approach, the two-step process increases the yield of all condensation products and maximizes production of the most valuable ketone isomers.

  该文介绍了一种两步醛缩合成过程。在碱存在下，α-蒎烯醛（ACA）和甲乙酮（MEK）反应，条件有效地产生了一种高收率的酮缩合物混合物。在有机磺酸存在下，脱水酮缩合物可以提供有价值的不饱和酮，作为合成檀香木产品的香料成分的中间体。与通常的一步法碱催化方法相比，这种两步法提高了所有缩合产物的产率，并最大化了最有价值的酮异构体的产量。
• [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 MAKING INTERMEDIATES FOR FRAGRANCE COMPONENTS FROM -CAMPHOLENIC ALDEHYDE
  申请人：Millennium Specialty Chemicals, Inc.

  公开号：EP2094634A2

  公开（公告）日：2009-09-02
• 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