(2R,4R,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-chromen-4-ol | 1157856-34-2

• 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,4R,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-chromen-4-ol
• 英文别名: (+)-(2R,4R,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-cromen-4-ol；(2r,4r,4Ar,7r,8ar)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2h-chromen-4-ol；(2R,4R,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyl-2,3,4a,5,6,7,8,8a-octahydrochromen-4-ol
• CAS: 1157856-34-2
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: ZZEIOCRRHXVKCH-WYGQYTNYSA-N

物化性质

• 熔点：
  101.8-102.4 °C
• 沸点：
  432.0±45.0 °C(predicted)
• 密度：
  1.063±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异胡薄荷醇 、 4-甲氧基苯甲醛 在 HCl treated montmorrilonite K₁₀ 作用下， 以 neat (no solvent) 为溶剂， 反应 0.05h， 以86%的产率得到(2R,4R,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-chromen-4-ol
  参考文献：
  名称：

  An Environmentally Benign Synthesis of Octahydro-2H-chromen-4-ols via Modified Montmorillonite K10 Catalyzed Prins Cyclization Reaction

  摘要：

  (-)-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。

  DOI：

  10.1055/s-0032-1316915

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。
• First example of a Prins–Ritter reaction on terpenoids: a diastereoselective route to novel 4-amido-octahydro-2H-chromenes
  作者：Barnali Sarmah、Gakul Baishya、Rajani K. Baruah

  DOI：10.1039/c4ra02124j

  日期：——

  (−)-Isopulegol was subjected to a triflic acid-promoted three-component Prins–Ritter reaction with a series of aldehydes to produce a library of novel 4-acetamido-octahydro-2H-chromene derivatives in good yields and high diastereoselectivities.

  （△）-异普尔戈尔与一系列醛类发生三氟乙酸催化的三组分普林斯-里特反应，生成一系列新型4-乙酰氨基-八氢-2H-苯并吡喃衍生物，产率较高，立体选择性较强。
• Prins-Arylthiolation Reaction on Terpenoids: Diastereoselective Synthesis of 4-Arylthiooctahydro-2<i>H</i>-chromenes
  作者：Barnali Sarmah、Gakul Baishya、Rajani K. Baruah

  DOI：10.1002/ejoc.201403080

  日期：2014.12

  (–)-Isopulegol undergoes Prins-arylthiolation with different aldehydes and cyclohexanone in the presence of HBF4·OEt2 to generate a library of 4-arylthiooctahydro-2H-chromene derivatives in good to excellent yields with moderate to high cis selectivity at ambient temperature in dichloromethane. Readily available HBF4·OEt2 as a catalyst outshines CF3CO2H, which is generally used in excess amounts in

  (-)-异胡薄荷醇在 HBF4·OEt2 存在下与不同的醛和环己酮进行 Prins-芳基硫醇化，生成 4-芳基硫代八氢-2H-色烯衍生物库，产率良好至极好，室温下在二氯甲烷中具有中等至高顺式选择性. 容易获得的 ·OEt2 作为催化剂优于 CF3CO2H，后者通常在 Prins 环化和多米诺 Prins-芳基硫醇化反应中过量使用。
• Acid-modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2<i>H</i> -Chromene Derivatives by the Reaction of Isopulegol with Aldehydes
  作者：Alexander Yu. Sidorenko、Anna V. Kravtsova、Atte Aho、Ivo Heinmaa、Konstantin P. Volcho、Nariman F. Salakhutdinov、Vladimir E. Agabekov、Dmitry Yu. Murzin

  DOI：10.1002/cctc.201800974

  日期：2018.9.20

  chromenol exhibiting high analgesic activity was achieved. An increase in stereoselectivity with a decrease in the halloysite drying temperature and catalyst acidity clearly indicates formation of 4R diastereomer on the weak Brønsted sites. This work is an example that control of the stereoselectivity of acid‐catalyzed organic reactions can be effectively carried out by varying water content on the aluminosilicate

  酸改性的高岭土纳米管被用于第一次作为用于施加烯丙醇的含氧杂环的合成立体选择性催化剂（ - ） -异胡薄荷醇缩合与醛的八氢-2 ħ -chromenol（4 - [R -和4小号-非对映体）为例。通过XRF，XRD，N 2吸附，带吡啶的FTIR和MAS NMR方法对催化剂进行了表征。在温和条件下，在环己烷中高比例的4 R / 4 S非对映异构体（7.6–14.5）大大超过了先前报道的结果。前所未有的选择性（79–83％）至4 R获得了具有高止痛活性的噻吩基取代的苯甲醇的异构体。立体选择性的增加，以及埃洛石干燥温度和催化剂酸度的降低，清楚地表明在弱的布朗斯台德位点上形成了4 R非对映异构体。这项工作就是一个例子，可以通过改变铝硅酸盐表面的水含量来有效地控制酸催化的有机反应的立体选择性。改性的埃洛石纳米管可以被认为是杂环化合物立体选择性合成的极有希望的催化剂。
• Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes
  作者：Irina V. Ilyina、Oksana S. Patrusheva、Vladimir V. Zarubaev、Maria A. Misiurina、Alexander V. Slita、Iana L. Esaulkova、Dina V. Korchagina、Yuri V. Gatilov、Sophia S. Borisevich、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmcl.2020.127677

  日期：2021.1

  We synthesized fluoro- and hydroxy-containing octahydro-2H-chromenes by the Prins reaction starting from a monoterpenoid (-)-isopulegol and a wide range of aromatic aldehydes in the presence of the BF₃∙Et₂O/H₂O system acting as both an acid catalyst and a fluorine source. Activity of the produced compounds against the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. The highest activity was demonstrated by fluoro- (11i) and hydroxy-containing (10i) derivatives of 2,4,6-trimethoxybenzaldehyde. The most pronounced virus-inhibiting effect of compounds 10i and 11i was observed at an early stage of infection. These compounds were supposed to be capable of binding to viral hemagglutinin, which is an agreement with data on the effect of compounds 10i and 11i on the viral fusogenic activity as well as by molecular docking studies.