(2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(4-chlorophenyl)-octahydro-2H-chromen-4-ol | 1231954-59-8

• 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)-4,7-dimethyl-2-(4-chlorophenyl)-octahydro-2H-chromen-4-ol
• 英文别名: (2R,4R,4aR,7R,8aR)-2-(4-chlorophenyl)-4,7-dimethyl-2,3,4a,5,6,7,8,8a-octahydrochromen-4-ol
• CAS: 1231954-59-8
• 化学式: C₁₇H₂₃ClO₂
• 分子量: 294.821
• InChiKey: RIXKEQRKIXWLEA-JSPVNYKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 异胡薄荷醇 在 HCl treated montmorrilonite K₁₀ 作用下， 以 neat (no solvent) 为溶剂， 反应 0.05h， 以66.667%的产率得到
  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

• 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。
• 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.
• 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.
• 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。