(2R,4S,4aR,7R,8aR)-2-(furan-2-yl)-4,7-dimethyloctahydro-2H-chromen-4-ol | 1447930-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,4S,4aR,7R,8aR)-2-(furan-2-yl)-4,7-dimethyloctahydro-2H-chromen-4-ol
• CAS: 1447930-46-2
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: UZWQAGVPBNQGMZ-BBIZWXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  42.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  糠醛 、 异胡薄荷醇 在 mononitrile K-10 作用下， 生成 (2R,4R,4aR,7R,8aR)-2-(furan-2-yl)-4,7-dimethyloctahydro-2H-chromen-4-ol 、 (2R,4S,4aR,7R,8aR)-2-(furan-2-yl)-4,7-dimethyloctahydro-2H-chromen-4-ol
  参考文献：
  名称：

  手性多氢醌对大麻素系统的影响

  摘要：

  通过单萜类（-）-异胡薄荷醇，（+）-新异胡薄荷醇和（1 R，2 R，6 S）-3-甲基-6-（prop-1-en- 2-基）环己-3-烯-1,2-二醇5与芳族和杂芳族醛。这些化合物的结构类似于植物大麻素，其中一些在体内具有镇痛作用。通过（-）-异胡薄荷醇与5-羟甲基糠醛的相互作用，然后用溴取代羟基并与胺进一步反应，获得了含氨基的多氢醌。首次研究了所有合成化合物影响内源性大麻素系统的能力。尽管多氢醌在10 µM的浓度下不显着结合CB 1和CB 2大麻受体，并且不抑制MAGL活性，但含3-溴噻吩取代基的异薄荷醇衍生物2i抑制FAAH活性，IC 50值为7.6 µM。因此，该化合物可增加内源性大麻素系统活性。

  DOI：

  10.1007/s00044-019-02294-9

文献信息

• Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF3·Et2O–H2O Catalytic System
  作者：Irina V. Il’ina、Oksana S. Patrusheva、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1007/s10593-020-02743-z

  日期：2020.7

  the monoterpenoid (–)-isopulegol and carbonyl compounds in the presence of the BF3·Et2O–H2O system, which acts as both an acid catalyst and a fluorine source. The use of the readily available and easy-to-use BF3·Et2O reagent makes this method of obtaining fluorine derivatives simple and practical.

  氟化八氢-2 H-色烯的合成是通过在BF 3 ·Et 2 O–H 2 O系统的存在下单萜类（–）-异胡薄荷醇与羰基化合物之间的Prins反应进行的。酸催化剂和氟源。使用易于获得且易于使用的BF 3 ·Et 2 O试剂，使得该获得氟衍生物的方法简单而实用。
• An Environmentally Benign Synthesis of Octahydro-2H-chromen-4-ols via Modified Montmorillonite K10 Catalyzed Prins Cyclization Reaction
  作者：Gakul Baishya、Barnali Sarmah、Nabajyoti Hazarika

  DOI：10.1055/s-0032-1316915

  日期：——

  (-)-Isopulegol undergoes Prins cyclization reaction in the presence of 20 wt% of acid-treated montmorillonite K10 to produce octahydro-2H-chromen-4-ols in good yields and with high cis selectivities under solvent-free conditions. The solid-acid catalyst can be reused without loss of its activity.

  (-)-异橙花叔醇在含有20%酸处理的蒙脱土K10催化下，能够在无溶剂条件下发生Prins环化反应，生成八氢-2H-色原-4-醇，具有良好的产率和高的顺式选择性。该固体酸催化剂在循环使用过程中不会失去活性。
• Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol
  作者：Ekaterina Nazimova、Alla Pavlova、Oksana Mikhalchenko、Irina Il’ina、Dina Korchagina、Tat’yana Tolstikova、Konstantin Volcho、Nariman Salakhutdinov

  DOI：10.1007/s00044-016-1573-3

  日期：2016.7

  A large set of chiral heterocyclic compounds with the octahydro-2H-chromene scaffold was first obtained by a reaction of (-)-isopulegol and (+)-neoisopulegol with furan-2-carbaldehyde, thiophene-2-carbaldehyde and their derivatives and isomers in the presence of montmorillonite K10 clay. Most of the (-)-isopulegol-derived compounds exhibited a significant analgesic activity in the acetic acid-induced writhing test. Compound 3b obtained by a reaction of (-)-isopulegol with thiophene-2-carbaldehyde demonstrated a significant analgesic effect in this test within 15 min after oral administration at the dose of 1 mg/kg and retains the effect for at least 24 h. Compound 3b exhibited analgesic activity in the hot plate test also. A change in the sulfur atom position in the aromatic ring was found to lead to the effect reversal in the hot plate test.