1-戊醇,5-[(四氢-2H-吡喃-2-基)氧代]-,4-甲基苯磺酸酯 | 123545-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-戊醇,5-[(四氢-2H-吡喃-2-基)氧代]-,4-甲基苯磺酸酯
• 英文名称: 1-<5-<2-(tetrahydropyranyloxy)>pentyl> p-toluenesulfonate
• 英文别名: 5-<(tetrahydro-2H-pyran-2-yl)oxy>pentyl toluene-4-sulfonate；5-[(tetrahydro-2H-pyran-2-yl)oxy]pentyl 4-methylbenzenesulfonate；HOCH2(CH2)3CH2OTs；5-(Oxan-2-yloxy)pentyl 4-methylbenzenesulfonate
• CAS: 123545-82-4
• 化学式: C₁₇H₂₆O₅S
• 分子量: 342.456
• InChiKey: RMNXUUFQWBMJCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  1-戊醇,5-[(四氢-2H-吡喃-2-基)氧代]-,4-甲基苯磺酸酯 在 sodium hydroxide 、 四丁基硫酸氢铵 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 101.0h， 生成 5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1-nonyl-undecyloxy)-pentan-1-ol
  参考文献：
  名称：

  New anionic glycophospholipids with two perfluorocarbon or two hydrocarbon or mixed hydrophobic chains

  摘要：

  Novel amphiphilic anionic sugar phosphates esterified by various hydrophobic double-chain tails were synthesized. They differ primarily by the design of their hydrophobic tail. Amphiphile 12a derives from phosphogalactose and has two perfluoroalkylated hydrophobic chains; 12b has a pentenyloxy spacer between the mixed hydrocarbon/fludrocarbon double-chain and the same head group; 12c and 14c are galactose and glucose derivatives with two hydrocarbon tail chains. All were prepared through a three-step H-phosphonate route: reaction of the hydrophobic double-chain alcohol on phosphorus trichloride (27-60%), followed by the addition of the appropriately protected sugar, by oxidation (50-81%), and finally by deprotection of the sugar (58-95%). The starting alcohols were prepared through conventional reactions. Their synthesis was however, difficult, essentially as a result of lesser reactivity, and of low solubility of some of the intermediates related to the presence of the bulky, strongly hydrophobic chains. Preliminary biocompatibility assays indicate a reduction in hemolytic activity by increasing the number of fluorinated chains or by increasing the total length, hence the hydrophobicity of the amphiphile. Acute toxicity tests indicate maximum intravenously tolerated doses in mice of ca. 500 mg/kg body weight for 12a and 12b.

  DOI：

  10.1016/0009-3084(95)02492-2
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 对甲苯磺酸 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-戊醇,5-[(四氢-2H-吡喃-2-基)氧代]-,4-甲基苯磺酸酯
  参考文献：
  名称：

  （5'-脱氧腺苷-5'-基）钴胺素（='Adenosylcobalamin'）类似物的合成和表征，其模拟了辅酶B 12依赖型重排的过渡态几何构型

  摘要：

  描述了五个（5'-脱氧腺苷-5'-基）钴胺素（=“腺苷钴胺素”）的五个新类似物1a-e的会聚合成。类似物1a–e带有低聚亚甲基链（C 3 –C 7），插入在腺苷部分的中央Co-原子和5'-O-原子之间，并被认为模仿了辅酶B 12-中的过渡态几何构型。催化重排。所有五个类似物均通过NMR，UV和FAB质谱表征。

  DOI：

  10.1002/hlca.19930760623

文献信息

• Polystyrene-supported GaCl3: A new, highly efficient and recyclable heterogeneous Lewis acid catalyst for tetrahydropyranylation of alcohols and phenols
  作者：Ali Rahmatpour

  DOI：10.1016/j.poly.2012.06.063

  日期：2012.8

  highly chemoselective method for tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst at room temperature is presented. In this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to the corresponding

  在聚苯乙烯负载的三氯化镓（PS / GaCl 3）存在下，用3,4-二氢-2 H-吡喃（DHP）对醇和酚进行四氢吡喃基化的一种新的，简单且高度化学选择性的方法）是在室温下具有高活性和可重复使用的非均相路易斯酸催化剂。在该催化体系中，伯，仲和叔醇以及苯酚以短的反应时间和高收率转化为相应的四氢吡喃基（THP）醚。异质催化剂在吡喃基化反应中具有高可重复使用性和稳定性，并且被回收了数次，其活性损失可忽略不计且催化剂浸出可忽略不计，并且也不需要再生。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。
• Disubstituted tetrahydrofurans and dioxolanes as platelet activating factor (PAF) antagonists
  作者：Javier Bartroli、Elena Carceller、Manuel Merlos、Julian Garcia-Rafanell、Javier Forn

  DOI：10.1021/jm00105a058

  日期：1991.1

  PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Several of these compounds exhibited more potent activity than the structurally related 2-[N-acetyl-N-[[[[2-methoxy-3-[(octadecylcarbamoyl) oxy]propoxy]carbonyl]amino]methyl]-1-ethylpyridinium chloride (CV-6209, 3) in the in vitro assay, whereas all showed less potency in the in vivo test. The role of both the substituent nature

  制备了一系列新的双取代的四氢呋喃和二氧戊环衍生物，并在PAF诱导的体外血小板聚集和体内低血压试验中评估了它们的PAF拮抗剂活性。这些化合物中的几种显示出比与结构相关的2- [N-乙酰基-N-[[[[2-甲氧基-3-[（十八烷基氨基甲酰基）氧基]丙氧基]羰基]氨基]甲基] -1-乙基吡啶鎓氯化物更有效的活性。 （CV-6209，3）在体外试验中，而在体内试验中均显示出较低的效价。讨论了取代基性质以及环中氧原子的位置和数量的作用。对这些核进行了定量SAR研究。
• A Highly Efficient Synthetic Protocol for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols
  作者：Abu T. Khan、Subrata Ghosh、Lokman H. Choudhury

  DOI：10.1002/ejoc.200500400

  日期：2005.11

  Bismuth(III) nitrate pentahydrate [Bi(NO3)3·5H2O] is found to be an effective catalyst for both tetrahydropyranylation and depyranylation of alcohols and phenols. Some of the major advantages of this protocol are: non-aqueous workup, good yields, the involvement of a less-expensive and nontoxic catalyst, and compatibility in the presence of a large number of other protecting groups. Notably, isopropylidene

  五水合硝酸铋 (III) [Bi(NO3)3·5H2O] 被发现是醇和酚的四氢吡喃化和去吡喃化的有效催化剂。该协议的一些主要优点是：非水后处理、良好的收率、价格较低且无毒的催化剂的参与，以及在存在大量其他保护基团的情况下的兼容性。值得注意的是，异丙叉、亚苄基和硫代缩醛基团在实验条件下也不受影响。值得注意的是，通过使用相同的催化剂，可以化学选择性地实现二醇和伯醇的选择性单保护。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Tetrabutylammonium tribromide (TBATB)-promoted tetrahydropyranylation/depyranylation of alcohols
  作者：Sarala Naik、Rangam Gopinath、Bhisma K Patel

  DOI：10.1016/s0040-4039(01)01599-4

  日期：2001.10

  Alcohols are tetrahydropyranylated rapidly in high yields in the presence of a catalytic amount of TBATB in dichloromethane at room temperature. Depyranylation to their parent alcohol is achieved in quantitative yields by merely changing the solvent to methanol.

  在室温下，在二氯甲烷中，在催化量的TBATB存在下，将酒精快速高产率地四氢吡喃化。仅通过将溶剂改为甲醇，即可定量获得脱吡喃基化为其母体醇。
• Synthetic Studies Directed toward Kaitocephalin: A Highly Stereocontrolled Route to the Right-Hand Pyrrolidine Core
  作者：Susumi Hatakeyama、Keisuke Takahashi、Natsumi Haraguchi、Jun Ishihara

  DOI：10.1055/s-2008-1042801

  日期：——

  A highly stereocontrolled method for the construction of the right-hand segment of kaitocephalin, an antagonist of AMPA/KA and NMDA glutamate receptors, has been developed employing palladium-catalyzed cyclization of an oxiranylacrylate at the quaternary center as the key step.

  一种高立体选择性的方法已经被开发用于构建kaitocephalin的右侧片段，这是一种对AMPA/KA和NMDA谷氨酸受体的拮抗剂，关键步骤是采用钯催化的环化反应，将氧杂环丙烯基丙烯酸酯在四次中心上进行反应。