(1R,2S,4S)-4-isopropyl-1-methyl-2-(o-tolylmethoxy)-7-oxabicyclo[2.2.1]heptane

• 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: (1R,2S,4S)-4-isopropyl-1-methyl-2-(o-tolylmethoxy)-7-oxabicyclo[2.2.1]heptane
• 英文别名: (1R,2S,4S)-cinmethylin；2-exo-[(2-methylphenyl)methoxy]-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane；Rel-cinmethylin；(1R,2S,4S)-1-methyl-2-[(2-methylphenyl)methoxy]-4-propan-2-yl-7-oxabicyclo[2.2.1]heptane
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: QMTNOLKHSWIQBE-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane 、 2-甲基苄溴 在 cesium chloride 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 66.0h， 以53%的产率得到(1R,2S,4S)-4-isopropyl-1-methyl-2-(o-tolylmethoxy)-7-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  [EN] A METHOD FOR SEPARATING OPTICALLY ACTIVE HYDROXY CINEOLE DERIVATIVES
  [FR] PROCÉDÉ DE SÉPARATION DE DÉRIVÉS D'HYDROXY CINÉOLE OPTIQUEMENT ACTIFS

  摘要：

  本发明涉及一种通过浸提和结晶分离光学活性羟基桉叶素衍生物的方法，以及通过该方法制备的纯度大于99.5％的对映纯光学活性羟基桉叶素衍生物。本发明还涉及使用根据本发明制备的对映体旋光异构体超过99.5％ee的所需对映体，用于合成对映纯7-氧杂双环[2.2.1]庚烷衍生物。

  公开号：

  WO2018210663A1

文献信息

• [EN] A PROCESS FOR PREPARING AN OPTICALLY ACTIVE CINEOLE DERIVATIVE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN DÉRIVÉ DE CINÉOLE OPTIQUEMENT ACTIF
  申请人：BASF AGRO BV

  公开号：WO2018210662A1

  公开（公告）日：2018-11-22

  The present invention relates to a process for preparing optically active 1,4-cineole derivatives by enzymatic resolution and enantiomerically pure optically active 1,4-cineole derivatives of purity greater than 99.9 % that have been prepared by this process. The present invention further relates to a process for preparing 7-oxabicyclo[2.2.1]heptane derivatives from the enantiomerically pure optically active 1,4-cineole derivatives.

  本发明涉及一种通过酶解和手性纯度大于99.9%的光学活性1,4-桉叶醇衍生物的制备过程。本发明还涉及一种从手性纯度高的光学活性1,4-桉叶醇衍生物制备7-氧杂双环[2.2.1]庚烷衍生物的过程。
• [EN] PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 2-EXO-(2-MÉTHYLBENZYLOXY)-1-MÉTHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE
  申请人：BASF AGRO BV

  公开号：WO2018177907A1

  公开（公告）日：2018-10-04

  This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the step of reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) (II), any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) (III), wherein X is a leaving group, in the presence of at least one base, at least one catalyst selected from rubidium salts, cesium salts and any combination thereof and at least one inert organic solvent S1.

  该发明涉及一种制备(±)-2-外消旋-(2-甲基苄氧基)-1-甲基-4-异丙基-7-氧杂双环[2.2.1]庚烷的过程，其化学式为(I)，任何其个别对映体或其非外消旋混合物，包括以下步骤：将(±)-2-外消旋-羟基-1-甲基-4-异丙基-7-氧杂双环[2.2.1]庚烷的化学式为(II)，任何其个别对映体或其非外消旋混合物与化学式(III)的2-甲基苄基化合物反应，其中X是一个脱离基，在至少一种碱、至少一种选择自铷盐、铯盐和二者任意组合的催化剂和至少一种惰性有机溶剂S1的存在下。
• Preparation of 2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes
  申请人：Shell Oil Company

  公开号：US04487945A1

  公开（公告）日：1984-12-11

  2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes are prepared by treating the corresponding cis-epoxycyclohexanol with acid in an inert solvent or by treating a 3-cyclohexen-1-ol which will produce the corresponding cis-epoxy alcohol successively or concurrently with an oxidizing agent and an acid in an inert solvent.

  2-外消旋-羟基-7-氧杂双环[2.2.1]庚烷可通过在惰性溶剂中用酸处理相应的顺环氧基环己醇来制备，或者通过在惰性溶剂中用氧化剂和酸同时或连续处理3-环己烯-1-醇来制备相应的顺环氧醇。
• [EN] PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 2-EXO- (2-MÉTHYLBENZYLOXY)-1-MÉTHYL-4-ISOPROPYL-7-OXABICYCLO [2.2.1] HEPTANE
  申请人：BASF AGRO BV

  公开号：WO2018050518A1

  公开（公告）日：2018-03-22

  This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso- propyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptaneof the formula (II), any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group in the presence of at least one base capable of forming water or a C1 -C 4 alkyl alcohol under the reaction conditions, and at least one inert organic sol- vent, and (b) simultaneously removing water, the C1-C4 alkyl alcoholor any mixture thereof from the reaction mixture.

  这项发明涉及制备(±)-2-外消旋-(2-甲基苄氧基)-1-甲基-4-异丙基-7-氧代-2-环丙基[2.2.1]庚烷的方法，其化学式为(I)，包括以下步骤：(a)将(±)-2-外消旋-羟基-1-甲基-4-异丙基-7-氧代-2-环丙基[2.2.1]庚烷的化学式(II)，其任一手性体或非旋光混合物与化学式(III)中X为脱离基的2-甲基苄化合物在至少一种能够在反应条件下生成水或C1-C4烷基醇的碱存在下反应，并在至少一种惰性有机溶剂中进行；(b)同时从反应混合物中移除水、C1-C4烷基醇或二者的混合物。
• [EN] PROCESS FOR PREPARING TERPINENE-4-OL<br/>[FR] PROCÉDÉ DE PRÉPARATION DE TERPINÈNE-4-OL
  申请人：BASF AGRO BV

  公开号：WO2017144336A1

  公开（公告）日：2017-08-31

  The present invention relates to a process for preparing terpinene-4-ol from limonene-4-ol via a hydrogenation reaction in the presence of a nickel catalyst.

  本发明涉及一种通过在镍催化剂存在下进行氢化反应从柠檬烯-4-醇制备萜品-4-醇的方法。