3-[(四氢-2H-吡喃-2-基)氧基]-1-丁醇 | 40595-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 3-[(四氢-2H-吡喃-2-基)氧基]-1-丁醇
• 英文名称: 3-Tetrahydropyranyloxybutan-1-ol
• 英文别名: 3-(tetrahydropyran-2-yloxy)butan-1-ol；3-(α-Tetrahydropyranyloxy)-1-butanol；1-Butanol, 3-[(tetrahydro-2H-pyran-2-yl)oxy]-；3-(oxan-2-yloxy)butan-1-ol
• CAS: 40595-23-1
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: LBRXDVACOOJMJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  298.3±30.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(四氢-2H-吡喃-2-基)氧基]-1-丁醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+/-)-3-tetrahydropyranyloxybutanal
  参考文献：
  名称：

  A Facile Total Synthesis of Neurotrophic Metabolite (+/-)-Neuchromenin

  摘要：

  描述了已知天然产物(+/-)-neuchromenin的合成，该产物能诱导PC12细胞的神经突起生长。总合成涉及从芝麻酚构建一条香豆素环，并通过Morita-Baylis-Hillman反应（MBH）将此中间体与醛偶联。MBH加成物在酸性条件下环化，随后去除一个亚甲基组，以在9个步骤中从芝麻酚获得(+/-)-neuchromenin。

  DOI：

  10.2174/15701786113106660088
• 作为产物：
  描述：

  ethyl 3-(tetrahydropyranyloxypropyl)butanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 3-[(四氢-2H-吡喃-2-基)氧基]-1-丁醇
  参考文献：
  名称：

  A Facile Total Synthesis of Neurotrophic Metabolite (+/-)-Neuchromenin

  摘要：

  描述了已知天然产物(+/-)-neuchromenin的合成，该产物能诱导PC12细胞的神经突起生长。总合成涉及从芝麻酚构建一条香豆素环，并通过Morita-Baylis-Hillman反应（MBH）将此中间体与醛偶联。MBH加成物在酸性条件下环化，随后去除一个亚甲基组，以在9个步骤中从芝麻酚获得(+/-)-neuchromenin。

  DOI：

  10.2174/15701786113106660088

文献信息

• Lanthanum trichloride: An efficient catalyst for the silylation of hydroxyl groups by activating hexamethyldisilazane (HMDS)
  作者：Akkirala Venkat Narsaiah

  DOI：10.1016/j.jorganchem.2007.05.002

  日期：2007.8

  A variety of hydroxy functional groups was protected as their corresponding trimethylsilyl ethers using HMDS in the presence of lanthanum trichloride. The catalyst LaCl3 activates the HMDS and accelerates the reaction under mild reaction conditions at room temperature to afford the corresponding silylated products in excellent yields.

  在三氯化镧存在下，使用HMDS将各种羟基官能团保护为其相应的三甲基甲硅烷基醚。催化剂LaCl 3活化HMDS，并在温和的反应条件下在室温下促进反应，以优异的产率提供相应的甲硅烷基化产物。
• Indium Tribromide: An Efficient Catalyst for the Silylation of Hydroxy Groups by the Activation of Hexamethyldisilazane
  作者：J. Yadav、B. Reddy、A. Basak、G. Baishya、A. Narsaiah

  DOI：10.1055/s-2006-950322

  日期：2006.11

  A variety of substrates containing hydroxy groups have been protected as their corresponding trimethylsilyl ethers using 1,1,1,3,3,3-hexamethyldisilazane in the presence of indium tribromide. The catalyst indium tribromide activates the 1,1,1,3,3,3-hexa­methyldisilazane and accelerates the reaction under mild reaction conditions at room temperature.

  多种含有羟基的底物已在三甲基硅醚的对应物中被保护，使用了在溴化铟存在下的1,1,1,3,3,3-己六甲基二硅氮。催化剂溴化铟激活了1,1,1,3,3,3-己六甲基二硅氮，并在室温的温和反应条件下加速反应。
• POLYMERIZABLE MONOMER, GRAFT COPOLYMER, AND SURFACE MODIFIER
  申请人：Tokyo University Of Science Educational Foundation Administrative Organization

  公开号：EP2330138A1

  公开（公告）日：2011-06-08

  The graft copolymer comprises a polymerizable monomer (A1) represented by general formula (III) and a polymerizable monomer (B1) containing a pyridyl group, and a ligand can be bonded via the functional group at the terminus of R3a. In the formula, R1a represents a polymerizable group, R2a represents an alkylene group having a carbon number of 2-5, R3a represents an organic group having at a terminus a functional group selected from among an azide group, a phenyl azide group, a carboxyl group, a primary to quaternary amino group, an acetal group, an aldehyde group, a thiol group, a disulfide group, an active ester group, a trialkoxysilyl group, and a polymerizable group, and n represents any integer from 5 to 20,000.

  接枝共聚物包括通式(III)表示的可聚合单体(A1)和含有吡啶基的可聚合单体(B1)，配体可通过 R3a 末端的官能团键合。在式中，R1a 代表可聚合基团，R2a 代表碳数为 2-5 的亚烷基，R3a 代表有机基团，其末端具有选自叠氮基团、苯基叠氮基团、羧基、伯羟基、羧基、酰胺基、酰胺基、酰胺基、酰胺基、酰胺基、酰胺基、酰胺基、酰胺基、酰胺基中的官能团、羧基、伯至季氨基、缩醛基、醛基、硫醇基、二硫化物基、活性酯基、三烷氧基硅烷基和可聚合基中选出的官能团，以及 n 代表 5 至 20,000 之间的任意整数。
• Werschkun, Barbara; Koenig, Wilfried A.; Kren, Vladimir, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2459 - 2466
  作者：Werschkun, Barbara、Koenig, Wilfried A.、Kren, Vladimir、Thiem, Joachim

  DOI：——

  日期：——
• 12-Substituted-13,14-dihydroretinols designed for affinity labeling of retinol binding- and processing proteins
  作者：Revital Yefidoff、Amnon Albeck

  DOI：10.1016/j.tet.2004.06.116

  日期：2004.9

  All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C-12 were designed to be affinity labels for retinol binding and processing proteins. Unlike other non-selective highly reactive affinity labels, these compounds carry a Michael acceptor type substitution at C-12 of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C-12 position of their retinol ligand. The synthetic route for these compounds is based on the Emmons-Horner reaction of a C15 aldehyde with an appropriate phosphonate bearing the desired electron-withdrawing group to be incorporated at the C-12 position of the retinol skeleton. (C) 2004 Elsevier Ltd. All rights reserved.