6-<(Tetrahydro-2H-pyran-2-yl)oxy>-2-hexanone | 64841-39-0

• 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: 6-<(Tetrahydro-2H-pyran-2-yl)oxy>-2-hexanone
• 英文别名: 6-(tetrahydro-2H-pyran-2-yloxy)-2-hexanone；6-(oxan-2-yloxy)hexan-2-one
• CAS: 64841-39-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: CSKYWPCFYZTNKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<(Tetrahydro-2H-pyran-2-yl)oxy>-2-hexanone 在 咪唑 、 magnesium 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 4-Methyl-4-<(trimethylsilyl)oxy>-8-<(tetrahydro-2H-pyran-2-yl)oxy>-1-octyne
  参考文献：
  名称：

  18-Cycloalkyl analogs of enisoprost

  摘要：

  By use of standard cuprate methodology, a series of 18-cycloalkyl analogues of enisoprost was prepared in an effort to impede omega chain metabolism and prolong duration of gastric antisecretory activity. An initial product of omega chain oxidation, the C-20 hydroxy analogue, was also synthesized for pharmacological comparison. The cyclopropyl, cyclobutyl, and cyclopentyl analogues were approximately one-fourth as potent as enisoprost in inhibiting gastric acid secretion, while the cyclohexyl and cycloheptyl analogues showed very weak activity, and the 20-hydroxy compound was inactive at a dose 100 times the ED50 of enisoprost. The cyclobutyl compound had a longer duration of antisecretory action than enisoprost and the other cycloalkyl analogues. The cycloalkyl analogues unexpectedly possessed low diarrheogenic activity in rats.

  DOI：

  10.1021/jm00125a013
• 作为产物：
  描述：

  5-已烯-2-酮 在 盐酸 、 sodium hydroxide 、 硼烷 、 双氧水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 7.0h， 生成 6-<(Tetrahydro-2H-pyran-2-yl)oxy>-2-hexanone
  参考文献：
  名称：

  18-Cycloalkyl analogs of enisoprost

  摘要：

  By use of standard cuprate methodology, a series of 18-cycloalkyl analogues of enisoprost was prepared in an effort to impede omega chain metabolism and prolong duration of gastric antisecretory activity. An initial product of omega chain oxidation, the C-20 hydroxy analogue, was also synthesized for pharmacological comparison. The cyclopropyl, cyclobutyl, and cyclopentyl analogues were approximately one-fourth as potent as enisoprost in inhibiting gastric acid secretion, while the cyclohexyl and cycloheptyl analogues showed very weak activity, and the 20-hydroxy compound was inactive at a dose 100 times the ED50 of enisoprost. The cyclobutyl compound had a longer duration of antisecretory action than enisoprost and the other cycloalkyl analogues. The cycloalkyl analogues unexpectedly possessed low diarrheogenic activity in rats.

  DOI：

  10.1021/jm00125a013

文献信息

• Wacker oxidation of terminal olefins in a mixture of [bmim][BF4] and water
  作者：I.A. Ansari、Sipak Joyasawal、Manoj K. Gupta、J.S. Yadav、R. Gree

  DOI：10.1016/j.tetlet.2005.09.013

  日期：2005.10

  simple and efficient PdCl2/CuCl catalyzed oxidation of alkenes has been successfully developed using a mixture of water and the ionic liquid [bmim][BF4] as solvent. Starting from various types of terminal olefins, the corresponding ketones have been prepared under mild reaction conditions and obtained in good to excellent yields after a simple extraction with diethyl ether. Furthermore, it was possible to

  使用水和离子液体[bmim] [BF 4 ]的混合物作为溶剂，已经成功开发了一种简单有效的PdCl 2 / CuCl催化的烯烃氧化方法。由各种类型的末端烯烃开始，已在温和的反应条件下制备了相应的酮，并在用二乙醚简单萃取后以良好或优异的收率得到了相应的酮。此外，可以回收和再利用离子液体和催化体系。
• Brønsted Base-Modulated Regioselective Pd-Catalyzed Intramolecular Aerobic Oxidative Amination of Alkenes: Formation of Seven-Membered Amides and Evidence for Allylic C−H Activation
  作者：Liang Wu、Shuifa Qiu、Guosheng Liu

  DOI：10.1021/ol900941t

  日期：2009.6.18

  A novel palladium-catalyzed intramolecular aerobic oxidative allylic C−H amination of olefins has been developed. Brønsted base can modulate the regioselectivity, favoring the formation of 7-membered rings. Mechanistic studies using deuterium-labeled substrates as probes support a rate-determining allylic C−H activation/irreversible reductive elimination pathway.

  已经开发了一种新型的钯催化的烯烃分子内需氧氧化烯丙基CH胺化反应。布朗斯台德碱可以调节区域选择性，有利于7元环的形成。使用氘标记的底物作为探针的机理研究支持决定速率的烯丙基CH活化/不可逆还原消除途径。
• Radical cyclization using a thioacetal group for radical generation
  作者：Atsushi Nishida、Norio Kawahara、Mayumi Nishida、Osamu Yonemitsu

  DOI：10.1016/0040-4020(96)00511-x

  日期：1996.7

  The generation and cyclization of several heterocyclic radicals were investigated. The hydrogen abstraction from 1,3-dithiane, 1,3-dithiolane, and 1,3-oxathiane rings by a benzophenone triplet generated the corresponding heterocyclic radicals, which gave the cyclized products by intramolecular addition to α,β-unsaturated esters. Diastereoselective radical cyclization using chiral acetals was also investigated

  研究了几种杂环基的产生和环化。通过二苯甲酮三联体从1,3-二硫杂环戊烷，1,3-二硫杂环戊烷和1,3-氧杂蒽环上夺氢产生了相应的杂环基，这些杂环基通过分子内加成α，β-不饱和酯而得到环化产物。还研究了使用手性缩醛的非对映选择性自由基环化。
• Regio- and Stereoselectivity of the Intramolecular C–H Insertion by Cyclopropylidenes Bearing a Remote Oxido Substituent
  作者：Toshiro Harada、Yasunari Yamaura、Akira Oku

  DOI：10.1246/bcsj.60.1715

  日期：1987.5

  (ω-Oxidoalkyl)cyclopropylidenes generated from (2,2-dibromo-1-methylcyclopropyl)-CH2–X–(CH2)n–OH (X=CH2 or O, n=1, 2) by the reaction with methyllithium underwent a regioselective intramolecular insertion into the C–H bond at the δ position to the carbenic carbon. The activation effect of the oxido substituent on the reactivity of C–H bonds is discussed on the basis of (1) the ratio of the insertion products

  由 (2,2-二溴-1-甲基环丙基)-CH2-X-( )n-OH (X= 或 O, n=1, 2) 与甲基锂反应生成的 (ω-氧化烷基) 环亚丙基区域选择性分子内插入碳碳的 δ 位置的 C-H 键。基于（1）插入产物与重排产物丙二烯醇的比率，和（2）本插入反应的内立体选择性，讨论了氧化取代基对 C-H 键反应性的活化作用。
• 3,4-Dihydro-4-oxo-2H-1-benzopyranyloxy alkanoic acid derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0261254A1

  公开（公告）日：1988-03-30

  It has been found that the novel compounds of the formula wherein R¹ is hydrogen or lower alkyl, R² is hydrogen or halogen, R³ is hydrogen or lower alkyl, R⁴ is hydrogen or lower alkyl, R⁵ is hydrogen, lower alkyl or aralkyl, X is alkylene and n is an integer from 1 to 6, the enantiomers thereof and, when R⁵ is hydrogen, the salts thereof with pharmaceutically acceptable bases have antiallergic properties and can accordingly be used as medicaments for the treatment or prevention of allergic conditions. The compounds of formula I can be manufactured by reacting a compound of the formula with a compound of the formula and optionally hydrolyzing the compound thus obtained.

  发现式中的新型化合物 其中 R¹ 是氢或低级烷基，R² 是氢或卤素，R³ 是氢或低级烷基，R⁴ 是氢或低级烷基，R⁵ 是氢、低级烷基或芳烷基，X 是亚烷基，n 是 1 至 6 的整数、 其对映体，以及当 R⁵ 为氢时，其与药学上可接受的碱的盐具有抗过敏特性，因此可用作治疗或预防过敏症的药物。式 I 的化合物可通过将式 I 的化合物与式 I 的化合物反应制得 与式 并可选择水解由此得到的化合物。