2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran | 72900-28-8

• 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-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran
• 英文别名: (Z)-1,4-di[(tetrahydro-2H-pyran-2-yl)oxy]but-2-ene；(Z)-1,4-bis(tetrahydro-2H-pyran-2-yloxy)but-2-ene；(Z)-1,4-di(2-tetrahydropyranyloxy)-but-2-ene；cis-2-buten-1,4-diol tetrahydropyranyl ether；2-[(Z)-4-(oxan-2-yloxy)but-2-enoxy]oxane
• CAS: 72900-28-8
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: GQFJVSJSWXVZFR-WAYWQWQTSA-N

物化性质

• 沸点：
  120-130 °C(Press: 0.4 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以94%的产率得到(tetrahydropyranyloxy)acetaldehyde
  参考文献：
  名称：

  Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1

  摘要：

  An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of the chiral linear precursor (a key to the synthesis) was achieved by the asymmetric aldol reaction followed by the computer-assisted predictive stereoselective intramolecular Diels-Alder reaction. The global antitumor activity of the totally synthetic 1 against a variety of human cancer cells was assessed using a panel of 39 human cancer cell lines (JFCR39), and it was shown that the synthetic 1 strongly inhibited the growth of several cancer cell lines at concentrations of less than 0.04 mu M. Biological assays of novel derivatives, 26 and 31, which have different side-chains at the C-4 positions in the Delta(1,2)-octalin backbone, disclosed the importance of the suitable structure of the side-chain containing conjugated multidouble bonds.

  DOI：

  10.1021/jm301695c
• 作为产物：
  描述：

  treo-2,3-dibromo-1,4-tetrahydropyranyloxybutane 在 1,2-双(二苯基膦)乙烷氯化镍 、 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran
  参考文献：
  名称：

  镍介导的从形成双键VIC -dibromides和乙基溴化镁

  摘要：

  VIC -dibromides通过使用NidppeCl催化量定量地召集到烯烃2，在THF将EtMgBr两个摩尔当量的存在。给出了反应的立体化学方面。

  DOI：

  10.1016/0040-4039(95)01988-t

文献信息

• Highly selective monotetrahydropyranylation of symmetrical diols catalysed by a strongly acidic ion-exchange resin
  作者：Takeshi Nishiguchi、Masahumi Kuroda、Masahiko Saitoh、Akiko Nishida、Shizuo Fujisaki

  DOI：10.1039/c39950002491

  日期：——

  Several primary and secondary symmetrical diols, ranging from propane-1,3-diol to decane-1,10-diol, are selectively monoprotected by monotetrahydropyranyl ether formation catalysed by a strongly acidic ion-exchange resin (Dowex 50w × 2, 50–100 mesh) in a 3,4-dihydro-2H-pyran-hydrocarbon mixture.

  几个选自丙二醇-1,3至癸二醇-1,10的主、次对称二醇，在强酸性离子交换树脂（Dowex 50w× 2，50-100目）催化下，以3,4-二氢-2H-吡喃-烃混合物为介质，发生单四氢吡喃醚选择性单保护反应。
• Lithium triflate (LiOTf) catalyzed efficient and chemoselective tetrahydropyranylation of alcohols and phenols under mild and neutral reaction conditions
  作者：Babak Karimi、Jafar Maleki

  DOI：10.1016/s0040-4039(02)00892-4

  日期：2002.7

  Different types of alcohols and phenols were effectively converted to the corresponding THP ethers in the presence of DHP and a catalytic amount of lithium trifluoromethanesulfonate (LiOTf) in refluxing 1,2-dichloroethane under essentially neutral reaction conditions. The method also shows good chemoselectivity for mono-tetrahydropyranylation of symmetrical diols.

  在DHP和催化量的三氟甲烷磺酸锂（LiOTf）的存在下，在基本中性的反应条件下，将不同类型的醇和酚有效地转化为相应的THP醚。该方法对对称二醇的单四氢吡喃基化反应也显示出良好的化学选择性。
• Indium triiodide catalysed one-step conversion of tetrahydropyranyl ethers to acetates with high selectivity
  作者：Brindaban C. Ranu、Alakananda Hajra

  DOI：10.1039/b100014b

  日期：——

  A very simple and efficient method has been developed for the chemoselective one-step conversion of tetrahydropyranyl ethers of primary alcohols to the corresponding acetates through an indium triiodide catalysed transesterification process in ethyl acetate.

  一种非常简单高效的方法被开发出来，可以通过在乙酸乙酯中以碘化铟为催化剂的转酯化过程，将初级醇的四氢吡喃醚选择性地一步转化为相应的醋酸酯。
• Highly selective one-pot conversion of THP and MOM ethers to acetates by indium triiodide-catalysed deprotection and subsequent transesterification by ethyl acetate
  作者：Brindaban C. Ranu、Alakananda Hajra

  DOI：10.1039/b104055n

  日期：——

  A simple and efficient method is developed for the chemoselective one-pot conversion of tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers of primary alcohols to the corresponding acetates by indium triiodide-catalysed deprotection and subsequent acetylation by ethyl acetate through a transesterification process.

  我们开发了一种简单而高效的方法，通过铟三碘催化去保护和随后的醋酸乙酯转酯化过程，将初级醇的四氢吡喃基（THP）和甲氧基甲基（MOM）醚选择性地一锅转化为相应的醋酸酯。
• InCl3 immobilized in ionic liquids: a novel and recyclable catalytic system for tetrahydropyranylation and furanylation of alcohols
  作者：Jhillu Singh Yadav、Basi. V. Subba Reddy、Dughani Gnaneshwar

  DOI：10.1039/b210044b

  日期：2003.1.20

  A mild and highly efficient method has been developed for the protection of hydroxyl compounds as tetrahydropyranyl and furanyl ethers using a catalytic amount of indium trichloride immobilized in 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid under mild conditions. A wide range of functional and protecting groups such as THP, TBDMS, TBDPS, PMB, MOM ethers, acetonides, olefins and epoxides are compatible with ionic liquids. Monoprotection of diols has also been achieved using this novel procedure.

  一种温和且高效的方法已被开发，用于在温和条件下使用少量氯化铟固定在1-丁基-3-甲基咪唑四氟磷酸盐离子液体中保护羟基化合物，形成四氢吡喃醚和呋喃醚。多种官能团和保护基，如THP、TBDMS、TBDPS、PMB、MOM醚、丙烯醇和环氧化物，与离子液体兼容。该新方法还实现了二醇的单保护。