trans-2-carbomethoxycyclohexan-1-ol | 936-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-carbomethoxycyclohexan-1-ol
• 英文别名: (+/-)-trans-2-Hydroxy-cyclohexancarbonsaeure-methylester；(+/-)-trans-2-Hydroxy-cyclohexan-carbonsaeure-(1)-methylester；trans-2-Methoxycarbonyl-cyclohexanol；(+/-)-trans-2-hydroxy-cyclohexanecarboxylic acid methyl ester；methyl (1S,2S)-2-hydroxycyclohexane-1-carboxylate
• CAS: 936-03-8；936-04-9；2236-11-5；13375-11-6；13375-12-7；22436-30-2；22436-31-3；145678-74-6；145678-79-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: IAJQZEQYGUQTQS-BQBZGAKWSA-N

物化性质

• 沸点：
  103-113 °C(Press: 5-8.5 Torr)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  trans-2-carbomethoxycyclohexan-1-ol 在 lithium aluminium tetrahydride 、 potassium acetate 作用下， 生成 3-<(acetyloxy)methyl>cyclohexene
  参考文献：
  名称：

  The Mechanism of the Prins Reaction. II. The Solvolysis of trans-2-Hydroxymethylcyclohexyl Brosylate and trans-2-Acetoxymethylcyclohexyl

  摘要：

  DOI：

  10.1021/ja00884a009
• 作为产物：
  描述：

  (E)-7-氧代庚-2-烯酸甲酯 在 Raney Ni (W-4) 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.5h， 生成 trans-2-carbomethoxycyclohexan-1-ol
  参考文献：
  名称：

  Efficient cyclization of ω-oxo-α,β-unsaturated esters using lithium thiolate-initiated Michael-aldol tandem reaction

  摘要：

  The reaction of omega-oxo-alpha,beta-unsaturated esters with lithium thiolates afforded the Michael-aldol tandem cyclization products in good to perfect stereoselectivity depending on the nature of thiolates. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01439-2

文献信息

• Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions
  作者：Tomohiro Maegawa、Akira Akashi、Kiichiro Yaguchi、Yohei Iwasaki、Masahiro Shigetsura、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/chem.200900361

  日期：2009.7.13

  An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H2 pressures (<10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are

  已经开发了基于使用异质铂族催化剂的有效和实用的芳烃加氢方法。Rh / C是最有效的芳环加氢催化剂，可以在中性条件下，在常压至中等H 2压力（<10 atm）下在i PrOH中进行。将各种芳烃（如烷基苯，苯甲酸，吡啶，呋喃）以良好或极好的收率氢化成相应的环己基和杂环化合物。Ru / C的使用比Rh / C便宜，它为氢化包括苯酚在内的芳烃提供了一种有效而实用的方法。在简单过滤后，两种催化剂都可以重复使用数次，而催化活性没有任何重大损失。
• [EN] DISACCHARIDES FOR DRUG DISCOVERY<br/>[FR] DISACCHARIDES POUR LA DECOUVERTE DE MEDICAMENTS
  申请人：ALCHEMIA PTY LTD

  公开号：WO2003093286A1

  公开（公告）日：2003-11-13

  Methods are described for the preparation of combinatorial libraries of potentially biologically active disaccharide compounds. These compounds are variously functionalized, with a view to varying lipid solubility size, function and other properties, with the particular aim of discovering novel drug or drug-like compounds, or compounds with useful properties. The invention provides intermediates, processes and synthetic strategies for the solution or solid phase synthesis of disaccharides, variously functionalised about the sugar ring, including the addition of aromaticity and charge, and the placement of pharmaceutically useful groups and isosteres.

  描述了制备可能具有生物活性的二糖化合物组合库的方法。这些化合物通过各种方式进行了官能化，以改变脂溶性、大小、功能和其他性质，特别是为了发现新型的药物或类似药物化合物，或者具有有用性质的化合物。该发明提供了中间体、过程和合成策略，用于二糖的溶液或固相合成，包括在糖环周围进行不同的官能化，引入芳香性和电荷，以及放置药物上有用的基团和等电子体。
• Enantioselective ketoester reductions in water: a comparison between microorganism- and ruthenium-catalyzed reactions
  作者：Saoussen Zeror、Jacqueline Collin、Jean-Claude Fiaud、Louisa Aribi Zouioueche

  DOI：10.1016/j.tetasy.2010.05.014

  日期：2010.5

  search for green chemistry methods for the enantioselective reduction of ketoesters Saccharomyces cerevisiae- and ruthenium-catalyzed reactions in water have been investigated. The highest enantiomeric excesses for the reduction of α- and β-ketoesters have been obtained by S. cerevisiae. Chiral ruthenium catalysts are active for the reduction of all ketoesters with low to moderate enantioselectivities

  在寻找绿色化学方法以对映体还原酮酸酯的过程中，已经研究了酿酒酵母和钌催化的水中反应。酿酒酵母获得了用于还原α-和β-酮酸酯的最高对映体过量。手性钌催化剂对于还原所有酮酯具有低到中等对映选择性的活性，这取决于底物和配体的性质。有趣的是，对于几种底物，已经根据催化方法或配体的结构获得了羟基酯的两种对映体。
• Hexafluoroisopropanol: A Powerful Solvent for the Hydrogenation of ­Functionalized Aromatic Compounds
  作者：Fabienne Fache、Olivier Piva

  DOI：10.1055/s-2004-825603

  日期：——

  Various substituted aromatic compounds have been reduced under H 2 using RuCl 3 . The fluorous solvent hexafluoroisopropanol turned out to be particularly efficient in the case of compounds difficult to reduce in organic solvents.

  已使用 RuCl 3 在 H 2 下还原了各​​种取代的芳族化合物。在有机溶剂中难以还原的化合物的情况下，氟溶剂六氟异丙醇被证明是特别有效的。
• Therapy for Australian cats with lymphosarcoma
  作者：R MALIK、LJ GABOR、SF FOSTER、BE McCORKELL、PJ CANFIELD

  DOI：10.1111/j.1751-0813.2001.tb10923.x

  日期：2001.12

  ObjectiveTo determine the response of Australian cats with lymphosarcoma to chemotherapy and/or surgery in relation to patient and tumour characteristics, haematological and serum biochemical values and retroviral status.DesignProspective study of 61 client‐owned cats with naturally‐occurring lymphosarcoma subjected to multi‐agent chemotherapy and/or surgery.ProcedureAn accepted chemotherapy protocol utilising l‐asparaginase, vincristine, cyclophosphamide, doxorubicin, methotrexate and prednisolone was modified and used to treat 60 cats with lymphosarcoma. Clinical findings were recorded before and during therapy. As far as practical, cases were followed to death, euthanasia or apparent cure. Owner satisfaction with the results of chemotherapy was determined using a questionnaire sent after the completion of chemotherapy.ResultsOne cat, with lymphosarcoma limited to a single mandibular lymph node, was treated using surgery alone and was cured. The other 60 cats were treated using multi‐agent chemotherapy, although seven cats with localised intestinal, ocular and subcutaneous lesions had these lesions partially (2 intestinal lesions) or completely (2 eyes, 2 intestinal lesions and a cluster of regional lymph nodes) resected prior to starting chemotherapy. The median survival time for these 60 cats was 116 days. Of the 60 cats, 48 rapidly went into complete remission following the administration of l‐asparaginase, vincristine and prednisolone (complete remission rate 80%) and these cats had a median survival of 187 days.Three cats were censored from further analysis as their long‐term survival data were uninterpretable because they died of causes unrelated to lymphosarcoma or were prematurely lost to follow‐up. Twenty cats were classed as ‘long‐term survivors’ based on survival time in excess of one year and at least 14 were ‘cured’ based on the absence of physical evidence of lymphosarcoma 2‐years after initiating treatment. In other words, of the 48 cats that reached complete remission, in excess of 29% were ‘cured’.Despite detailed analysis, few meaningful prognostic indicators based on patient or tumour characteristics were identified, although long‐term survivors were more likely to be less than 4‐years (P = 0.04) and to have tumours of the T‐cell phenotype (P = 0.06). Excluding the one FeLV ELISA‐positive cat with mediastinal LSA, 7 of 9 cats less than 4 years‐of‐age were long‐term survivors (median survival time >1271 days). There was a strong association between achieving complete remission and long‐term survival (P = 0.003).On the basis of 27 replies to a questionnaire, owners were generally very satisfied with the response to chemotherapy, irrespective of the survival time of the individual patient. Eighty five percent of owners expressed complete satisfaction with their decision to pursue chemotherapy and 70% believed their cat's health status improved during the first 2‐weeks of treatment. Importantly, 78% of owners considered that chemotherapy required a very substantial time commitment on their part.ConclusionsIt was possible to cure approximately one quarter of cats with lymphosarcoma using sequential multi‐agent chemotherapy and/or surgery. FeLV‐negative cats younger than 4 years (typically with mediastinal lymphosarcoma) had a particularly favourable prognosis. The decision to embark on chemotherapy should be based on the results of induction chemotherapy with l‐asparaginase, vincristine and prednisolone, as the response to this was a good predictor of long‐term survival. Cats surviving the first 16 weeks of chemotherapy generally enjoyed robust remissions (in excess of 1 year) or were cured of their malignancy.

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