1,3,3,5,6-pentamethyl-bicyclo[2.2.2]octa-5-en-2-one | 90052-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,3,5,6-pentamethyl-bicyclo[2.2.2]octa-5-en-2-one
• 英文别名: 1,3,3,5,6-Pentamethylbicyclo[2.2.2]oct-5-en-2-one
• CAS: 90052-78-1
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: MGZLYKWFWJURBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5,6-Bis(hydroxymethyl)-1,3,3-trimethylbicyclo[2.2.2]-octa-5,7-dien-2-one diacetate 在 钯 氮 、 氢气 、 甲苯 作用下， 以 异丙醇 为溶剂， 22.0~85.0 ℃ 、107.27 MPa 条件下， 反应 1.87h， 以to yield 10.1 grams of 1,3,3,5,6-pentamethyl-bicyclo[2.2.2]octa-5-en-2-one的产率得到1,3,3,5,6-pentamethyl-bicyclo[2.2.2]octa-5-en-2-one
  参考文献：
  名称：

  Process for augmenting or enhancing aroma of consumable material by

  摘要：

  本文描述了1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇为异构体混合物及其异构体形式的结构：##STR1##以及它们在增强香水组合物、带香物品和古龙水的香气方面的用途。

  公开号：

  US04512902A1

文献信息

• Perfume or cologne containing
  申请人：International Flavors & Fragrances Inc.

  公开号：US04434085A1

  公开（公告）日：1984-02-28

  Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

  本文描述了1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇作为异构体混合物及其异构体形式的结构：##STR1## 以及其在增强香水组合物、香水制品和古龙香水的香气方面的用途。还描述了一种新的制备1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇的方法，首先将具有结构的化合物与具有结构的化合物反应，以产生根据结构定义的酮：##STR4## 然后氢化形成具有结构的化合物：##STR5## 进一步氢化形成具有结构的酮：##STR6## 这种酮与CH.sub.3 M反应，其中M代表Li或MgX，其中X为氯、溴或碘，以形成根据结构定义的有机金属中间体：##STR7## 然后用稀酸水解这些化合物，形成我们发明的有机感官有用的1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇异构体，其结构定义如下：##STR8##
• 1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]-oct-5-en-2-ol, process for
  申请人：International Flavors & Fragrances Inc.

  公开号：US04471135A1

  公开（公告）日：1984-09-11

  Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol.

  本文介绍了1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇的异构体混合物及其异构形式的结构：##STR1##以及它们在增强香水组合物，香水制品和古龙香水的香气方面的用途。还介绍了一种制备1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇的新工艺。
• 1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, and organoleptic
  申请人：International Flavors & Fragrances Inc.

  公开号：US04514324A1

  公开（公告）日：1985-04-30

  Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

  本文描述了1,2,3,3,5,6-六甲基双环[2.2.2]辛-5-烯-2-醇的异构体混合物及其异构体形式，具有以下结构：##STR1## 并且在香水组合物、香氛制品和古龙香水中增强或增强其香气的用途。还描述了一种新的制备1,2,3,3,5,6-六甲基双环[2.2.2]辛-5-烯-2-醇的方法，首先将具有以下结构的化合物：##STR2## 与具有以下结构的化合物反应：##STR3## 以产生根据以下结构定义的酮：##STR4## 然后加氢形成具有以下结构的化合物：##STR5## 进一步加氢形成具有以下结构的酮：##STR6## 然后将该酮与CH.sub.3 M反应，其中M表示Li或MgX，其中X为氯、溴或碘，以形成根据以下结构定义的有机金属中间体：##STR7## 然后用稀酸水解这些化合物，形成本发明的1,2,3,3,5,6-六甲基双环[2.2.2]辛-5-烯-2-醇的感官有用的异构体，其根据以下结构定义：##STR8##
• 1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for
  申请人：International Flavors & Fragrances Inc.

  公开号：US04549972A1

  公开（公告）日：1985-10-29

  Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

  本文描述了1,2,3,3,5,6-六甲基双环[2.2.2]辛-5-烯-2-醇作为异构体混合物和其异构体形式，具有以下结构：##STR1##以及它们在增强香水组合物、带香物品和古龙香水的香气方面的用途。本文还描述了一种新的制备1,2,3,3,5,6-六甲基双环[2.2.2]辛-5-烯-2-醇的过程，首先将具有以下结构的化合物：##STR2##与具有以下结构的化合物反应：##STR3##以产生根据以下结构定义的酮：##STR4##，然后将其氢化以形成具有以下结构的化合物：##STR5##并进一步氢化以形成具有以下结构的酮：##STR6##这种酮与CH.sub.3 M反应，其中M代表Li或MgX，其中X为氯、溴或碘，以形成根据以下结构定义的有机金属中间体：##STR7##然后用稀酸水解这些化合物以形成本发明的1,2,3,3,5,6-六甲基双环[2.2.2]辛-5-烯-2-醇的有机感官有用的异构体，其根据以下结构定义：##STR8##
• 1,2,3,3,5,6,-Hexamethyl-bicyclo(2.2.2)-oct-5-en-2-ol, process for producing same, intermediates useful in said process and organoleptic uses of same
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0148301A2

  公开（公告）日：1985-07-17

  Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: with the compound having the structure: in order to produce the ketone defined according to the structure: which is hydrogenated to form the compound having the structure: and further hydrogenated to form the ketone having the structure: This ketone is reacted with CH3M wherein M represents Li or MgX and wherein X is chloro. bromo or iodo to form the organometallic intermediate defined according to the structures: These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures:

  描述了 1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇异构体混合物及其具有以下结构的异构体形式： 及其在增加或提升香水组合物、香水制品和古龙水香气方面的用途。 此外，还介绍了一种制备 1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇的新工艺，该工艺首先使具有以下结构的化合物发生反应： 与具有以下结构的化合物反应 的化合物发生反应，生成按结构定义的酮： 再经氢化生成结构如下的化合物： 并进一步氢化形成具有以下结构的酮： 该酮与 CH3M 反应，其中 M 代表 Li 或 MgX，X 代表氯、溴或碘，形成根据 结构定义的有机金属中间体： 然后用稀酸水解这些化合物，形成本发明的具有有机oleptically useful的1,2,3,3,5,6-六甲基-双环[2.2.2]辛-5-烯-2-醇异构体：