(1R,6R)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal | 1370053-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,6R)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal
• 英文别名: (r)-2-((r)-2,2-Dimethylcyclopent-3-enyl)-2-hydroxypropanal；(2R)-2-[(1R)-2,2-dimethylcyclopent-3-en-1-yl]-2-hydroxypropanal
• CAS: 1370053-16-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: QBPSJHLRQMSTJA-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,6R)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 (R)-1-adamantan-1-ylamino-2-((R)-2,2-dimethylcyclopent-3-en-1-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis of New Compounds Combining Adamantanamine and Monoterpene Fragments and their Antiviral Activity Against Influenza Virus A(H1N1)pdm09

  摘要：

  合成了一类具有金刚烷和单萜骨架的新型含氮化合物。 研究了这些胺类产物对流感病毒A/California/07/09（H1N1）pdm09的抗病毒活性。 引入单萜片段后，金刚烷胺衍生物对耐金刚烷胺病毒的抗病毒活性增强：大多数合成胺的选择性指数均高于利巴韦林和金刚烷胺。

  DOI：

  10.2174/1570180811310060002
• 作为产物：
  描述：

  (1R,2R,4S,5R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^4.2]octan-5-ol 在 montmorillonite clay K₁₀ 作用下， 生成 (1R,6R)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal
  参考文献：
  名称：

  Synthesis of New Compounds Combining Adamantanamine and Monoterpene Fragments and their Antiviral Activity Against Influenza Virus A(H1N1)pdm09

  摘要：

  合成了一类具有金刚烷和单萜骨架的新型含氮化合物。 研究了这些胺类产物对流感病毒A/California/07/09（H1N1）pdm09的抗病毒活性。 引入单萜片段后，金刚烷胺衍生物对耐金刚烷胺病毒的抗病毒活性增强：大多数合成胺的选择性指数均高于利巴韦林和金刚烷胺。

  DOI：

  10.2174/1570180811310060002

文献信息

• Synthesis and analgesic activity of monoterpenoid-derived 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ols
  作者：Svetlana Kurbakova、Irina Il’ina、Alla Pavlova、Dina Korchagina、Olga Yarovaya、Tat’yana Tolstikova、Konstantin Volcho、Nariman Salakhutdinov

  DOI：10.1007/s00044-013-0772-4

  日期：2014.4

  A new series of chiral heterocyclic compounds with frameworks of different types were synthesized by reactions of verbenol epoxide with aromatic aldehydes in the presence of montmorillonite clay. The analgesic activity of compounds with frameworks of 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol type was studied in vivo. The majority of these compounds showed a significant

  在蒙脱土的存在下，通过马来酸环氧化物与芳族醛的反应合成了一系列具有不同骨架的手性杂环化合物。研究了具有2-芳基-4,4,7-三甲基-4a，5,8,8a-四氢-4 H-苯并[ d ] [1,3]二恶英-8-ol型骨架的化合物的镇痛作用体内。这些化合物中的大多数在乙酸诱导的扭体试验中显示出显着的镇痛活性。两种化合物在热板试验中也显示出镇痛活性。在乙酸诱导的扭体试验中，对于芳基为4-氯苯基取代基的化合物，ED 50被确定为4.5 mg / kg。在两个试验中，具有4-硝基苯基取代基的化合物均显示出高镇痛活性。
• The First Synthesis of (4<i>S</i>,5<i>R</i>,6<i>R</i>)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid
  作者：Oleg V. Ardashov、Yuliya S. Demidova、Dina V. Korchagina、Konstantin P. Volcho、Irina L. Simakova、Nariman F. Salakhutdinov

  DOI：10.1002/hlca.201500125

  日期：2015.10

  A putative acid metabolite of a novel highly effective antiparkinsonian agent, (4S,5R,6R)‐5,6‐dihydroxy‐4‐(prop‐1‐en‐2‐yl)cyclohex‐1‐ene‐1‐carboxylic acid (5), was synthesized for the first time. Several synthetic approaches based on different transformations of O‐bearing monoterpenoids of the pinane and p‐menthane series were developed and tested in the course of the study. Acid 5 was synthesized

  新型高效抗帕金森病药物的推定酸代谢物（4 S，5 R，6 R）‐5,6 ‐二羟基‐ 4‐（丙‐ 1 ‐‐‐‐ 2‐yl）环己基‐1‐ ‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐首次合成的羧酸（5）。在研究过程中开发并测试了几种基于the烷和对-薄荷烷系列的含氧单萜类化合物的不同转化的合成方法。酸5是从市售的单萜类化合物（-）-马鞭草酮合成的，分8个步骤，总收率为4.4％。
• Compounds Combining Aminoadamantane and Monoterpene Moieties: Cytotoxicity and Mutagenic Effects
  作者：Evgeniy Suslov、Konstantin Ponomarev、Artem Rogachev、Michail Pokrovsky、Andrey Pokrovsky、Maria Pykhtina、Anatoly Beklemishev、Dina Korchagina、Konstantin Volcho、Nariman Salakhutdinov

  DOI：10.2174/1573406411666150518110053

  日期：2015.9.22

  A series of secondary amines combining monoterpenoid and aminoadamantane moieties have been synthesized. Their cytotoxic activity against human cancer cells CEM-13, MT-4, and U-937 has been studied for the first time. Most of the obtained compounds exhibited a significant cytotoxic activity with the median cytotoxic dose (CTD50) ranging from 6 to 84 µM. The most promising results were obtained for compound 2b which was synthesized from 1-aminoadamantane and (-)-myrtenal and revealed a high activity against all tumor lines used (CTD50 = 12÷21 µM) along with low toxicity with respect to MDCK cells (CTD50 = 1500 µM). The synthesized amines do not exert the genotoxic effect on cells of the biosensor strain based on recombinant E. coli cells bearing the pRAC-gfp plasmid.

  一系列结合单萜类和氨基阿曼坦基团的二级胺已被合成。它们对人癌细胞CEM-13、MT-4和U-937的细胞毒性活性首次进行了研究。大多数合成的化合物表现出显著的细胞毒性活性，中位细胞毒性剂量（CTD50）在6至84 µM之间。化合物2b的结果最为突出，它是由1-氨基阿曼坦和（-）-美尔亭醛合成的，并表现出对所有使用的肿瘤细胞系的高活性（CTD50 = 12÷21 µM），同时对MDCK细胞的毒性较低（CTD50 = 1500 µM）。合成的胺对基于重组大肠杆菌细胞（携带pRAC-gfp质粒）的生物传感器菌株细胞没有诱变毒性作用。
• Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure
  作者：Yu.S. Demidova、O.V. Ardashov、O.A. Simakova、I.L. Simakova、K.P. Volcho、N.F. Salakhutdinov、D.Yu. Murzin

  DOI：10.1016/j.molcata.2013.09.016

  日期：2014.7

  A novel method of (1S,2R,3R,5R)-6,6-dimethy1-4-methylenebicyclo[3.1.1]heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene alpha-hydroxy ketone. (C) 2013 Elsevier B.V. All rights reserved.
• Chiral schiff bases synthesized from terpenes of pinane series in asymmetric metall complex oxidation of sulfides
  作者：I. V. Il’ina、E. A. Koneva、D. V. Korchagina、G. E. Sal’nikov、A. M. Genaev、K. P. Volcho、N. F. Salakhutdinov

  DOI：10.1134/s1070428012020108

  日期：2012.2

  The absolute configuration of alpha-hydroxyaldehyde obtained from verbenol epoxide in the presence of clay was determined. Two new Schiff bases were synthesized from the aldehyde obtained. The compounds can be used as ligands in the asymmetric vanadium-catalyzed oxidation of sulfides to sulfoxides. The structure of initial sulfides significantly affects the value of the enantiomeric excess in the obtained sulfoxides: the highest enantiomeric excess is observed in the oxidation of thioanisole.