isopiperitenol

• 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: isopiperitenol
• 英文别名: (+)-p-menthadiene-3-ol；(6S)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-ol
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: OLAKPNFIICOONC-RGURZIINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isopiperitenol 在 chromium(VI) oxide 作用下， 生成 D-胡椒酮
  参考文献：
  名称：

  3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

  摘要：

  Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022
• 作为产物：
  描述：

  3-甲基-6-(1-甲基乙烯基)-2-环己烯-1-酮 在 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以92%的产率得到isopiperitenol
  参考文献：
  名称：

  四氢大麻素家族结构多样的天然产物的无保护基的对映体特异性总合成物。

  摘要：

  已经开发出一种简单的，高度非对映选择性的路易斯酸催化的环状烯丙基醇与间苯二酚衍生物的Friedel-Crafts偶联。该方法适用于结构多样的天然产物，如马卡儿酚-D，Delta（8）-THC，Delta（9）-THC，epi-perrottetinene及其类似物的对映体特异性全合成。天然产物及其对映异构体的合成均以高原子经济性，无保护基的方式，最长的线性序列少于6个步骤，从R-（+）和S-开始的非常好的总收率完成（-）-柠檬烯。

  DOI：

  10.1039/c4cc08562k

文献信息

• Enantiospecific Total Syntheses and Assignment of Absolute Configuration of Cannabinol-Skeletal Carbazole Alkaloids Murrayamines-O and -P
  作者：Dattatraya H. Dethe、Saikat Das、Balu D. Dherange、Samarpita Mahapatra

  DOI：10.1002/chem.201406434

  日期：2015.6.1

  First enantiospecific total syntheses of the cannabinol‐skeletal carbazole alkaloids murrayamines‐O and ‐P isolated from root barks of Murraya euchrestifoli, have been accomplished by highly diastereoselective, Lewis acid catalyzed coupling reactions of commercially available monoterpenes with carbazole derivative, which in addition to confirming the structure also established the absolute configuration

  从Murraya euchrestifoli的根皮中分离出的大麻酚-骨架咔唑生物碱murrayamines-O和-P的首个对映体总合成是通过高度非对映选择性的路易斯酸催化的市售单萜与咔唑衍生物的偶联反应完成的，此外还证实了该结构还建立了天然产品的绝对配置。天然产物及其对映异构体的合成均以高原子经济性，无保护基团的方式完成，并以六步最长的线性顺序由市售苯胺衍生物和马鞭草醇合成。
• Enantiospecific Total Syntheses of (+)-Hapalindole H and (−)-12-<i>epi</i> -Hapalindole U
  作者：Dattatraya H. Dethe、Saikat Das、Vijay B. Kumar、Nisar A. Mir

  DOI：10.1002/chem.201800970

  日期：2018.6.26

  Enantiospecific total syntheses of (+)‐hapalindole H and (−)‐12‐epi‐hapalindole U as well as the formal syntheses of (+)‐hapalindole Q and (+)‐12‐epi‐fischerindole U isothiocyanate have been described. Key steps of our approach feature expedient, highly regio‐ and diastereoselective Lewis acid catalyzed Friedel–Crafts reaction of indole with cyclic allylic alcohols and intramolecular reductive Heck

  已经描述了（+）-萘吲哚H和（-）-12- Epi- hapalindole U的对映体特异性合成，以及（+）-萘吲哚Q和（+）-12- epi- fischerindole U异硫氰酸酯的形式合成。我们方法的关键步骤具有便捷的区域选择性和非对映选择性的路易斯酸催化吲哚与环状烯丙基醇的Friedel-Crafts反应和分子内还原性Heck反应。合成途径的效率还依赖于从位阻位点驱动的炔基铝酸盐络合物驱动的区域选择性亲核性环氧化合物的开放。
• [EN] CONTINUOS FLOW SYNTHESIS OF CANNABIDIOL<br/>[FR] SYNTHÈSE DE FLUX CONTINU DE CANNABIDIOL
  申请人：INDENA SPA

  公开号：WO2020099283A1

  公开（公告）日：2020-05-22

  A process for the synthesis of Cannabidiol of formula (1): (1) is herein disclosed. The process comprises contacting a solution [solution (S1)] of (+)-p-mentha-diene-3-ol of formula (4) (4) or an ester thereof and olivetol of formula (3): (3) with a solution [solution (S2)] of a non-supported Lewis acid in a continuous flow reactor and treatment of the resulting mixture with a basic solution. The process offers the advantage that it can be conveniently carried out on an industrialscale while avoiding the formation of abnormal CBD and THC (Δ9-tetrahydrocannabinol).

  本文公开了一种合成式（1）的大麻二酚的方法。该过程包括将式（4）（4）或其酯的(+)-对薄荷二烯-3-醇的溶液[S1溶液]和式（3）的橄榄酚的溶液[S2溶液]与非支持式路易斯酸在连续流反应器中接触，并用碱性溶液处理所得混合物。该过程的优点是可以方便地在工业规模上进行，同时避免了异常CBD和THC（Δ9-四氢大麻酚）的形成。
• [EN] METHOD FOR PREPARING CANNABIDIOL COMPOUND<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ DE CANNABIDIOL<br/>[ZH] 大麻二酚类化合物的制备方法
  申请人：TOPHARMAN SHANGHAI CO LTD

  公开号：WO2020233502A1

  公开（公告）日：2020-11-26

  本发明公开了大麻二酚及其类似物的制备方法，该方法通过使间二苯酚衍生物与薄荷基-2,8-二烯-1-醇或其衍生物反应来实现。本发明方法具有化学反应选择性高、操作简便等优点。
• METHOD FOR PREPARING CANNABIDIOL COMPOUND
  申请人：TOPHARMAN SHANGHAI CO., LTD.

  公开号：US20220204431A1

  公开（公告）日：2022-06-30

  Disclosed is a method for preparing cannabidiol and analogues thereof; the method is implemented by means of reacting a resorcinol derivative with menthyl-2,8-dien-1-ol or a derivative thereof. The method of the present invention has advantages of such as high chemical reaction selectivity and simple operation.

  揭示了一种制备大麻二酚及其类似物的方法；该方法是通过将间苯二酚衍生物与薄荷醇-2,8-二烯-1-醇或其衍生物反应实现的。本发明的方法具有高化学反应选择性和简单操作等优点。