2-(R,S)-(hex-4-ynyloxy)tetrahydropyran | 85355-30-2

• 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: 2-(R,S)-(hex-4-ynyloxy)tetrahydropyran
• 英文别名: 2-Hex-4-ynoxyoxane
• CAS: 85355-30-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: XXFQQNSLEUNPJE-UHFFFAOYSA-N

物化性质

• 沸点：
  269.8±35.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(R,S)-(hex-4-ynyloxy)tetrahydropyran 在 盐酸 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 7.0h， 生成 6-碘-2-己炔
  参考文献：
  名称：

  [EN] STABILIZED POLYPEPTIDES AND USES THEREOF
  [FR] POLYPEPTIDES STABILISÉS ET UTILISATIONS DE CES DERNIERS

  摘要：

  公开号：

  WO2015051030A8
• 作为产物：
  描述：

  2-(3-溴丙氧基)四氢-2H-吡喃 在 正丁基锂 、 四甲基乙二胺 作用下， 反应 16.5h， 生成 2-(R,S)-(hex-4-ynyloxy)tetrahydropyran
  参考文献：
  名称：

  Synthesis of medium ring ethers. Part 3. Disproof of the proposed 2,8-disubstituted oxocane structure for gloeosporone. Synthesis of pseudo-gloeosporone

  摘要：

  Synthesis of the cis- and trans-2,8-disubstituted oxocane derivatives 2 and 3 (carrying the unusual gamma,delta-diketohexanecarboxylic acid side chain) by ozonolysis of the alkynes 14 and 18 (prepared respectively from the alcohols 11 and 15) demonstrated unequivocally that neither of these compounds nor their hydroxy-gamma-lactone ring (lactol) tautomers 1 corresponded to the naturally occurring fungal self germination inhibitor gloeosporone. A study of 4,5-dioxohexanoic itself 9 revealed a remarkably low tendency to exist as its hydroxy-gamma-lactone (lactol) tautomer 10.

  DOI：

  10.1039/p19920000095

文献信息

• Synthesis of naphthoquinone antibiotics by intramolecular alkyne cycloaddition to carbene-chromium complexes
  作者：M.F. Semmelhack、Joseph J. Bozell、Leonard Keller、Tadahisa Sato、E.J. Spiess、W. Wulff、A. Zask

  DOI：10.1016/s0040-4020(01)91420-6

  日期：1985.1

  The reaction of carbene-chromium complexes with alkynes provides a direct route to naphthoquinone derivatives and is the key step in a new approach to the isochromanone antibiotics exemplified by deoxyfrenolicin (1) and nanaomycin A (2). While the regioselectivity of intermolecular addition of the appropriate unsymmetrical disubstituted alkyne is unfavourable, two successful approaches have been developed

  卡宾-铬配合物与炔烃的反应提供了萘醌衍生物的直接途径，并且是异脱蒽酮抗生素（以脱氧肾上腺素（1）和纳那霉素A（2）为代表）的新方法的关键步骤。尽管分子间添加适当的不对称二取代炔烃的区域选择性不利，但已经开发出两种成功的方法。烯丙基乙炔以高区域选择性与甲氧基-（邻甲氧基苯基）亚甲基-Cr（CO）5反应。溴化，锂化和与乙醛反应生成所需的前体。烷氧基palladation导致吡喃环的形成和乙酸酯侧链的引入。按照先前的程序，纳那霉素A（2）产生。更趋同的替代方案涉及炔烃与亚烷基-铬单元的分子内环加成。一系列模型环化确定了可行性，并制备了带有乙二醇侧链的炔烃。乙二醇单元用作将炔烃保持在适当位置以进行环化的系链，并允许在以后的阶段轻松除去。脱氧肾上腺素（1）是在高度收敛和高效的过程中生产的。
• Tricyclic Sulfonamide Compounds and Methods of Making and Using Same
  申请人：Cramp Susan Mary

  公开号：US20140073623A1

  公开（公告）日：2014-03-13

  The invention provides tricyclic sulfonamide compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  该发明提供了三环磺酰胺化合物及其在治疗医学疾病，如肥胖症方面的用途。还提供了制备各种三环化合物的药物组合物和方法。考虑到这些化合物具有对甲硫氨酰基氨肽酶2的活性。
• TRICYCLIC SULFONAMIDE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：Zafgen, Inc.

  公开号：US20160256469A1

  公开（公告）日：2016-09-08

  The invention provides tricyclic sulfonamide compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  本发明提供了三环磺酰胺类化合物及其在治疗医学疾病，如肥胖症方面的应用。还提供了制备各种三环化合物的制药组合物和方法。这些化合物被认为具有对甲硫氨酰氨肽酶2的活性。
• Vinyl cations. 40. .pi.- and .sigma.-Routes to vinyl cations. Solvolyses of 2-methylcyclohexenyl, cyclopentylideneethyl, hex-5-yn-1-yl, and related triflates
  作者：Michael Hanack、Karl Albrecht Fuchs、Clair J. Collins

  DOI：10.1021/ja00350a044

  日期：1983.6
• Intramolecular Cyclization of β-Alkynylpropanamides to γ-Alkylidene-γ-butyrolactams
  作者：Yuji Koseki、Shuichi Kusano、Tatsuo Nagasaka

  DOI：10.1016/s0040-4039(98)00520-6

  日期：1998.5

  A general method for the base-catalized intramolecular cyclization of beta-alkynylpropanamides 1 to gamma-alkylidene-gamma-butyrolactames 2 (and 3) was established. Reactions of beta-alkynylamides 1c-h, possessing alkyl groups at the terminal acetylenes, in the presence of a catalytic amount of LiN(TMS)(2)/AgOTf (= 2:1) in toluene gave exclusively (Z)-alkylidenelactames 2c-h in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.