(±)-2-exo-hydroxy-1-methyl-4-isopropyl-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: (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane
• 英文别名: (1S,2R,4R)-1-methyl-4-propan-2-yl-7-oxabicyclo[2.2.1]heptan-2-ol
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: IFQZADDJTDGGCP-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane 生成 (1S,2R,4R)-1-methyl-2-phenylmethoxy-4-propan-2-yl-7-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  PAYNE, G. B.;SOLOWAY, S. B.;POWELL, J. E.;ROMAN, S. A.;KOLLMEYER, W. D.

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-桉叶素 以8%的产率得到
  参考文献：
  名称：

  ASAKAWA, YOSHINORI;MATSUDA, REIKO;TORI, MOTOO;HASHIMOTO, TOSHIHIRO, PHYTOCHEMISTRY, 27,(1988) N 12, C. 3861-3869

  摘要：

  DOI：

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。
• Preparation of biologically active substances and animal and microbial metabolites from menthols, cineoles and kauranes
  作者：Yoshinori Asakawa、Reiko Matsuda、Motoo Tori、Toshihiro Hashimoto

  DOI：10.1016/0031-9422(88)83033-4

  日期：1988.1

  and their structures elucidated by NMR spectroscopy. Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity. Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included. From ent-kauranes, a plant growth inhibitory diterpene alcohol, (−)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.

  摘要 间氯过苯甲酸或干臭氧氧化了六种单萜类化合物 l-薄荷醇、l-乙酸薄荷酯、异薄荷醇、新薄荷醇、1,4-桉树脑和 1,8-桉树脑和一种双萜烃 ent-kaurene。得到各种羟基化产物及其核磁共振谱阐明的结构。一些羟基化薄荷醇显示出植物生长抑制和强烈的驱蚊活性。在羟基化桉树脑中，包括桉树脑的微生物和动物代谢物。从 ent-kaurane 中获得了植物生长抑制性二萜醇 (-)-16α-羟基 kaurane 以及 16α-kauran-13α-ol。
• Herbicidal Activity of Cineole Derivatives
  作者：Allan F. M. Barton、Bernard Dell、Allan R. Knight

  DOI：10.1021/jf101827v

  日期：2010.9.22

  dose-dependent herbicidal activity against annual ryegrass and radish with many of the derivatives showing improved herbicidal activity relative to 1,8-cineole and high-cineole eucalyptus oil. Increased activity of cineole ester derivatives compared to their associated hydroxy-cineole and carboxylic acid was not observed. No relationship between lipophilicity of the carboxylic acid portion of cineole ester derivatives

  精油及其成分具有作为生态可接受的农药的潜力，也可能具有新颖的作用方式。在这项工作中，制备了大多数桉树油中主要成分天然单萜1,8-cineole 3和1,4-cineole 4的羟基和酯衍生物，并针对一年生黑麦草（黑麦草）进行了芽前除草活性。和萝卜（萝卜）变种 Long Scarlet（Long Scarlet）在基于实验室的生物测定法中进行了研究。1,8-桉树脑，桉树油和所有衍生物对一年生黑麦草和萝卜均表现出剂量依赖性的除草活性，其中许多衍生物相对于1,8-桉树脑和高桉树脑的桉树油具有更好的除草活性。与它们相关的羟基-桉树脑和羧酸相比，未观察到桉树脑酯衍生物的活性增加。没有观察到桉树脑酯衍生物的羧酸部分的亲脂性与除草活性之间的关系。结果表明这些桉树脑衍生物可能是环境可接受的除草剂。
• [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。
• [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。