(2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(4-nitrophenyl)-octahydro-2H-chromen-4-ol | 1231954-62-3

• 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,4R,4aR,7R,8aR)-4,7-dimethyl-2-(4-nitrophenyl)-octahydro-2H-chromen-4-ol
• 英文别名: (2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(4-nitrophenyl)-2,3,4a,5,6,7,8,8a-octahydrochromen-4-ol
• CAS: 1231954-62-3
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: OPBWRIJLUQYAHJ-JSPVNYKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 异胡薄荷醇 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(4-nitrophenyl)-octahydro-2H-chromen-4-ol 、 (2R,4S,4aR,7R,8aR)-4,7-dimethyl-2-(4-nitrophenyl)-octahydro-2H-chromen-4-ol
  参考文献：
  名称：

  Sc(OTf)3-catalyzed one-pot ene-Prins cyclization: a novel synthesis of octahydro-2H-chromen-4-ols

  摘要：

  (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.

  DOI：

  10.1016/j.tetlet.2010.03.100

文献信息

• Effect of chiral polyhydrochromenes on cannabinoid system
  作者：Nikolai S. Li-Zhulanov、Irina V. Il’ina、Andrea Chicca、Patricia Schenker、Oksana S. Patrusheva、Ekaterina V. Nazimova、Dina V. Korchagina、Mikhail Krasavin、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1007/s00044-019-02294-9

  日期：2019.4

  reactions of monoterpenoids (−)-isopulegol, (+)-neoisopulegol and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 5 with aromatic and heteroaromatic aldehydes. These compounds resemble in structure phytocannabinoids, some of them demonstrated analgesic activity in vivo. Polyhydrochromenes containing amino groups were obtained through the interaction of (−)-isopulegol with 5-hydroxymethylfurfural

  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。
• 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。
• Brønsted acid catalyzed Prins-Ritter reaction for selective synthesis of terpenoid-derived 4-amidotetrahydropyran compounds
  作者：A.Yu. Sidorenko、Yu.M. Kurban、A.F. Peixoto、N.S. Li-Zhulanov、J.E. Sánchez-Velandia、A. Aho、J. Wärnå、Y. Gu、K.P. Volcho、N.F. Salakhutdinov、D.Yu. Murzin、V.E. Agabekov

  DOI：10.1016/j.apcata.2022.118967

  日期：2023.1

  nanotubes) has been studied as catalysts in the cascade Prins-Ritter reaction of (-)-isopulegol with benzaldehyde and acetonitrile for synthesis of octahydro-2H-chromene amides (as 4R- and 4S-isomers). A high selectivity to these products at 30 °C in the presence of H2O was observed on catalysts modified with chlorosulfonic acid (CSA) reaching 84% (4R/4S of 5.7) in the case of biochar, while a relatively

  许多 SO 3 H 功能化固体（生物炭、蒙脱石、碳和埃洛石纳米管）已被研究作为催化剂在 (-)-异胡薄荷醇与苯甲醛和乙腈的级联 Prins-Ritter 反应中用于合成八氢-2 H-色烯酰胺（作为 4 R - 和 4 S - 异构体）。在生物炭的情况下，在氯磺酸 (CSA) 改性的催化剂上观察到在 30 °C 下在 H 2 O 存在下对这些产物的高选择性达到 84%（4 R /4 S为 5.7），而相对较大的octahydro-2 H的量-色烯醇（高达 31%）是 Prins 缩合的产物，在 2-（4-氯磺酰基苯基）乙基三甲氧基硅烷 (CSP) 功能化的材料上形成。尽管 Prins 缩合在弱酸位点上有效进行，但 Prins-Ritter 反应需要具有强 (0.33 – 5.8 mmol/g) Brønsted 酸度的硫酸化材料。CSP 功能化的催化剂是稳定的，而对于氯磺酸改性的材料，观察到
• 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.