trans-1-methanesulfonyloxy-4-(tetrahydropyran-2-yloxy)-2-butene | 119343-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: trans-1-methanesulfonyloxy-4-(tetrahydropyran-2-yloxy)-2-butene
• 英文别名: [(E)-4-(oxan-2-yloxy)but-2-enyl] methanesulfonate
• CAS: 119343-28-1
• 化学式: C₁₀H₁₈O₅S
• 分子量: 250.316
• InChiKey: FBHBVJNFTPSVDP-SNAWJCMRSA-N

物化性质

• 沸点：
  418.0±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-1-methanesulfonyloxy-4-(tetrahydropyran-2-yloxy)-2-butene 在 copper (I) iodide lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2-((E)-8-Benzyloxy-oct-2-en-5-ynyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  通过立体选择性分子内溴醚化对映异构合成多取代呋喃

  摘要：

  描述了通过手性烯醇的对映选择性构造和立体选择性溴环化来立体选择性地控制2，5-二烷基，3-取代的呋喃的合成。

  DOI：

  10.1016/0040-4039(88)85109-8
• 作为产物：
  描述：

  4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 trans-1-methanesulfonyloxy-4-(tetrahydropyran-2-yloxy)-2-butene
  参考文献：
  名称：

  通过立体选择性分子内溴醚化对映异构合成多取代呋喃

  摘要：

  描述了通过手性烯醇的对映选择性构造和立体选择性溴环化来立体选择性地控制2，5-二烷基，3-取代的呋喃的合成。

  DOI：

  10.1016/0040-4039(88)85109-8

文献信息

• Carboxylic acid derivatives and drugs containing the same as the active ingredient
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06664281B1

  公开（公告）日：2003-12-16

  A peroxisome proliferator activated receptor regulator containing a carboxylic acid derivative of formula (I) (wherein all symbols are as defined in the specification), a non-toxic acid thereof or a hydrate thereof as active ingredient. Because of having an effect of regulating PPAR, a compound of formula (I) is useful as a hypoglycemic agent, a hypolipidemic agent, a preventive and/or a remedy for diseases associating metabolic disorders (diabetes, obesity, syndrome X, hypercholesterolemia, hyperlipoproteinemia, etc.), hyperlipemia, atherosclerosis, hypertension, circulatory diseases, overeating, coronary heart diseases, etc., an HDL cholesterol-elevating agent, an LDL cholesterol and/or VLDL cholesterol-lowering agent and a drug for relief from risk factors of diabetes or syndrome X.

  一种过氧化物酶体增殖激活受体调节剂，含有公式（I）的羧酸衍生物（其中所有符号如规范中定义），其无毒酸或水合物作为活性成分。由于具有调节PPAR的作用，公式（I）的化合物作为降糖剂、降脂剂、预防和/或治疗代谢紊乱疾病（糖尿病、肥胖、综合征X、高胆固醇血症、高脂蛋白血症等）、高脂血症、动脉粥样硬化、高血压、循环系统疾病、暴饮暴食、冠心病等，以及升高HDL胆固醇的药物、降低LDL胆固醇和/或VLDL胆固醇的药物，以及缓解糖尿病或综合征X的危险因素的药物。
• Carboxylic acid derivative and a pharmaceutical composition containing the derivative as active ingredient
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US20040087636A1

  公开（公告）日：2004-05-06

  A peroxisome proliferator activated receptor regulator containing a carboxylic acid derivative of formula (I) 1 (wherein all symbols are as defined in the specification), a non-toxic acid thereof or a hydrate thereof as active ingredient. Because of having an effect of regulating PPAR, a compound of formula (I) is useful as a hypoglycemic agent, a hypolipidemic agent, a preventive and/or a remedy for diseases associating metabolic disorders (diabetes, obesity, syndrome X, hypercholesterolemia, hyperlipoproteinemia, etc.), hyperlipemia, atherosclerosis, hypertension, circulatory diseases, overeating, coronary heart diseases, etc., an HDL cholesterol-elevating agent, an LDL cholesterol and/or VLDL cholesterol-lowering agent and a drug for relief from, risk factors of diabetes or syndrome X.

  一种过氧化物酶体增殖激活受体调节剂，包含公式（I）1的羧酸衍生物（其中所有符号如说明书中所定义），其非毒性酸或水合物作为活性成分。由于具有调节PPAR的作用，公式（I）的化合物可用作降糖剂、降脂剂、预防和/或治疗代谢紊乱相关疾病（糖尿病、肥胖症、X综合症、高胆固醇血症、高脂蛋白血症等）、高脂血症、动脉硬化、高血压、循环系统疾病、过度进食、冠心病等，是一种提高HDL胆固醇的药物、降低LDL胆固醇和/或VLDL胆固醇的药物，并可用于缓解糖尿病或X综合症的风险因素。
• CARBOXYLIC ACID DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1108713A1

  公开（公告）日：2001-06-20

  A peroxisome proliferator activated receptor regulator containing a carboxylic acid derivative of formula (I) (wherein all symbols are as defined in the specification), a non-toxic acid thereof or a hydrate thereof as active ingredient. Because of having an effect of regulating PPAR, a compound of formula (I) is useful as a hypoglycemic agent, a hypolipidemic agent, a preventive and/or a remedy for diseases associating metabolic disorders (diabetes, obesity, syndrome X, hypercholesterolemia, hyperlipoproteinemia, etc.), hyperlipemia, atherosclerosis, hypertension, circulatory diseases, overeating, coronary heart diseases, etc., an HDL cholesterol-elevating agent, an LDL cholesterol and/or VLDL cholesterol-lowering agent and a drug for relief from risk factors of diabetes or syndrome X.

  一种含有式 (I) 羧酸衍生物的过氧化物酶体增殖物激活受体调节剂 (其中所有符号如说明书中所定义）的羧酸衍生物、其无毒酸或其水合物作为活性成分。 由于具有调节 PPAR 的作用，式（I）化合物可用作降糖药、降脂药、预防和/或治疗与代谢紊乱（糖尿病、肥胖症、X 综合征、高胆固醇血症、高脂蛋白血症等）、高血脂症、动脉粥样硬化、高血压、循环系统疾病、暴饮暴食、冠心病等有关的疾病、提高高密度脂蛋白胆固醇的药物、降低低密度脂蛋白胆固醇和/或低密度脂蛋白胆固醇的药物以及缓解糖尿病或 X 综合征危险因素的药物。
• EP1108713
  申请人：——

  公开号：——

  公开（公告）日：——
• Stereocontrolled Synthesis of Cyclic Ethers by Intramolecular Hetero-Michael Addition. 5. Synthesis of All Diastereoisomers of 2,3,5,6-Tetrasubstituted Tetrahydropyrans
  作者：Juan M. Betancort、Víctor S. Martín、José M. Padrón、José M. Palazón、Miguel A. Ramírez、Marcos A. Soler

  DOI：10.1021/jo9619241

  日期：1997.7.1

  A systematic approach to the enantiomeric synthesis of all possible diastereoisomers of 2,6-dialkyl-3,5-dioxytetrahydropyrans is described. The key step in the described methodology is the intramolecular cyclization of enantiomerically enriched (greater than or equal to 95% ee) 7-hydroxy-4-(benzoyloxy)-2,3-unsaturated esters. Infused systems, six of the eight diastereoisomers for one enantiomeric series were synthesized using this procedure as a key step. Using those with the suitable stereochemistry, the two left were synthesized by simple chemical transformations: in one case by the basic isomerization of the carbon with the (methoxycarbonyl)methyl substituent or by a Mitsunobu inversion of a secondary alcohol available from the benzoyloxy group,in the remaining one by a consecutive sequence of oxidation and reduction reactions again over the free secondary alcohol. The stereochemistry of the intramolecular hetero-Michael addition leading to 2,3-disubstituted tetrahydropyrans is highly predictable when kinetic conditions (low temperature and sodium or potassium bases) are used and can be rationalized by invoking a model of a chair-like transition state in which the benzoyloxy group is located in the equatorial mode and the stereochemical course of the approach of the alpha,beta-unsaturated ester is controlled by the geometry of the double bond. As a rule of thumb, the cyclization using E double bonds yielded cis-2,3-disubstituted tetrahydropyrans, while (Z)-unsaturated esters yielded the trans compounds. This empirical rule is followed in highly substituted systems, leading to fused 2,3,5,6-tetrasubstituted tetrahydropyrans, with the same absolute configuration in the carbon where the nucleophilic oxygen is located and the one where the benzoyloxy group is located. Those systems having opposite configurations yield the same trans-2,3-disubstituted compound. The isomerization under thermodynamic conditions (room or higher temperature with excess of base) of the diastereoisomers with the (methoxycarbonyl)methyl substituent in the axial mode led quantitatively to those in which such a group was located equatorially. The scope and limitations of the method are described in both the synthesis of the unsaturated precursor and the stereochemistry reached in the cyclization step.