(+)-(2R,4S,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-cromen-4-ol | 1157856-35-3

• 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-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-cromen-4-ol
• 英文别名: (2R,4S,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyl-2,3,4a,5,6,7,8,8a-octahydrochromen-4-ol
• CAS: 1157856-35-3
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: ZZEIOCRRHXVKCH-YXWSMURKSA-N

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 acid-modified halloysite nanotubes 作用下， 以 环己烷 为溶剂， 反应 0.25h， 生成 (2R,4R,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-chromen-4-ol 、 (+)-(2R,4S,4aR,7R,8aR)-2-(4-methoxyphenyl)-4,7-dimethyloctahydro-2H-cromen-4-ol
  参考文献：
  名称：

  酸改性的埃洛石纳米管作为立体选择性催化剂，通过异戊二醇与醛的反应合成2H-H烯衍生物

  摘要：

  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。

  DOI：

  10.1002/cctc.201800974

文献信息

• 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。
• 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.
• An expeditious synthesis of hexahydrobenzo[f]isochromenes and of hexahydrobenzo[f]isoquinoline via iodine-catalyzed Prins and aza-Prins cyclization
  作者：Luiz F. Silva、Samir A. Quintiliano

  DOI：10.1016/j.tetlet.2009.02.202

  日期：2009.5

  Homoallylic alcohols (primary, secondary, or tertiary containing an endocyclic or an exocyclic double bond) react with equimolar amounts of aldehydes (aliphatic or aromatic) and ketones (aliphatic) in the presence of 5 mol % of iodine. This Prins cyclization was used in the preparation of hexahydrobenzo[f]isochromenes and of a 4-hydroxy-tetrahydropyran, in 54-81% yield. The procedure is also efficient for an aza-Prins cyclization of a homoallylic sulfonamide and benzaldehyde, producing a hexahydrobenzo[f]isoquinoline. (C) 2009 Elsevier Ltd. All rights reserved.
• Sc(OTf)3-catalyzed one-pot ene-Prins cyclization: a novel synthesis of octahydro-2H-chromen-4-ols
  作者：J.S. Yadav、B.V. Subba Reddy、A.V. Ganesh、G.G.K.S. Narayana Kumar

  DOI：10.1016/j.tetlet.2010.03.100

  日期：2010.6

  (R)-Citronellal undergoes initial ene reaction followed by Prins cyclization with aldehydes in the presence of 5 mol % of scandium triflate at ambient temperature to furnish octahydro-2H-chromen-4-ols in good yields and with high cis-selectivity. The use of scandium triflate makes this procedure simple, more convenient, and practical. (C) 2010 Elsevier Ltd. All rights reserved.