5-羟基戊基苯基酮 | 17851-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-羟基戊基苯基酮
• 英文名称: 6-hydroxy-1-phenylhexan-1-one
• 英文别名: 5-hydroxypentyl phenyl ketone；5-Benzoyl-pentanol-(1)；5-Benzoylpentan-1-ol
• CAS: 17851-49-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: PUATWLVUUBATLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-羟基戊基苯基酮 在 2,6-二甲基吡啶 、 四乙基溴化铵 、 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到6-溴-1-苯基己烷-1-酮
  参考文献：
  名称：

  Halogenation of Primary Alcohols Using a Tetraethylammonium Halide/[Et₂NSF₂]BF₄ Combination

  摘要：

  The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et2NSF2]BF4 (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.

  DOI：

  10.1021/ol302496q
• 作为产物：
  描述：

  Grignard reagent of 5-chloro-pentanol pyrannyl ether 在 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 5-羟基戊基苯基酮
  参考文献：
  名称：

  氧化重氮烷烃的新型环化反应：1-取代的环烯烃的形成

  摘要：

  δ-羟基丁基酮和ε-羟基戊基酮甲苯磺酰azo的二碱金属盐在二甘醇二甲醚中在80-120°C的温度下热分解，分别生成1-取代的环戊烯和环己烯。

  DOI：

  10.1016/s0040-4039(00)89170-4

文献信息

• [EN] INHIBITORS OF PI3K-DELTA AND METHODS OF THEIR USE AND MANUFACTURE<br/>[FR] INHIBITEUR DE PI3K-DELTA ET PROCÉDÉS D'UTILISATION ET DE FABRICATION CORRESPONDANTS
  申请人：EXELIXIS INC

  公开号：WO2012037226A1

  公开（公告）日：2012-03-22

  The invention is directed to Compounds of Formula I: and pharmaceutically acceptable salts or solvates thereof, as well as methods of making and using the compounds.

  这项发明涉及到式I的化合物及其药用可接受的盐或溶剂合物，以及制备和使用这些化合物的方法。
• Oxidative α-C–C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O₂ at Room Temperature via Iron Photocatalysis
  作者：Zongnan Zhang、Guoxiang Zhang、Ni Xiong、Ting Xue、Junjie Zhang、Lu Bai、Qinyue Guo、Rong Zeng

  DOI：10.1021/acs.orglett.1c00556

  日期：2021.4.16

  cleavage of unfunctionalized secondary (2°) and tertiary alcohols (3°) is essential for valorization of macromolecules and biopolymers. We developed a blue-light-driven iron catalysis for aerobic oxidation of 2° and 3° alcohols to acids via α-C–C bond cleavages at room temperature. The first example of oxygenation of the simple tertiary alcohols was reported. The iron catalyst and blue light play critical

  未官能化的仲醇（2°）和叔醇（3°）的选择性α-CC键断裂对于大分子和生物聚合物的增值至关重要。我们开发了一种蓝光驱动的铁催化剂，用于在室温下通过α-CC键断裂将2°和3°醇有氧氧化为酸。报道了简单叔醇氧化的第一个例子。铁催化剂和蓝光起着至关重要的作用，可以使醇类形成高反应性的O自由基，并随后发生两次α-CC键断裂。
• Quinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05180742A1

  公开（公告）日：1993-01-19

  Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.dbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturated fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.2 receptor antagonism, or production inhibitory activity of 5-lipoxygenase metabolites in mammals, and of use as drugs, such as antiasthmatic, antiallergic agent and cerebral-circulatory metabolism ameliorating agent.

  通式为：##STR1##的醌衍生物（其中R.sup.1和R.sup.2相同或不同，且独立地为氢原子或甲基或甲氧基，或R.sup.1和R.sup.2结合在一起表示--CH.dbd.CH--CH.dbd.CH--R.sup.3为氢原子或甲基；R.sup.4为可以被取代的脂肪、芳香或杂环基团；R.sup.5为甲基或甲氧基、可以被取代的羟甲基或可以酯化或酰胺化的羧基；Z为--C.dbd.C--，--CH.dbd.CH--，##STR2##所表示的基团；n为0到10的整数；m为0到3的整数；k为0到5的整数，但是在m为2或3的情况下，Z和k可以在括号内的重复单元中任意变化）是新颖的化合物，具有改善多不饱和脂肪酸代谢的作用，特别是对脂质过氧化物的产生抑制活性（抗氧化活性）、血栓素A.sub.2受体拮抗作用，或对哺乳动物中5-脂氧合酶代谢产物的产生抑制活性，并可用作药物，如抗哮喘、抗过敏剂和改善脑循环代谢的药剂。
• Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
  作者：Lei Tao、Xueying Guo、Jie Li、Ruoling Li、Zhenyang Lin、Wanxiang Zhao

  DOI：10.1021/jacs.0c07854

  日期：2020.10.21

  The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes

  已经开发了铑催化的酮与 B2pin2 的脱氧和硼酸化，从而有效地形成烯烃、乙烯基硼酸酯和乙烯基二硼酸酯。这些反应的特点是反应条件温和，底物范围广，官能团兼容性好。机理研究支持酮最初经过 Rh 催化脱氧以通过硼烯醇化物中间体得到烯烃，随后 Rh 催化的烯烃脱氢硼化导致乙烯基硼酸酯和二硼化产物的形成，这也得到 DFT 计算的支持。
• Secondary Phosphine Oxides as Multitalented Preligands En Route to the Chemoselective Palladium-Catalyzed Oxidation of Alcohols
  作者：Alexandre Vasseur、Romain Membrat、David Gatineau、Alphonse Tenaglia、Didier Nuel、Laurent Giordano

  DOI：10.1002/cctc.201601261

  日期：2017.3.8

  Secondary phosphine oxides O=PHR2 (SPOs) were identified as multitalented preligands for the chemoselective Pd‐catalyzed oxidation of alcohols by a hydrogen‐abstracting methodology. SPOs were found to promote the hydrogen‐abstraction step as well as hydrogen transfer to a Michael acceptor by generating a putative active H−Pd species. The catalytic system operates under neutral conditions and was proven

  通过吸氢方法，仲膦氧化物O = PHR 2（SPOs）被鉴定为化学选择的Pd催化醇氧化的多态预配体。发现SPO通过产生推定的活性H-Pd物种来促进氢的吸收步骤以及氢向迈克尔受体的转移。该催化体系在中性条件下运行，并被证明与底物中的各种亲电子和亲核官能团以及对水和空气敏感的官能团兼容。