5-羟基-7-苯基庚烷-3-酮 | 106353-51-9

• 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: 5-羟基-7-苯基庚烷-3-酮
• 英文名称: 5-hydroxy-7-phenyl-heptan-3-one
• 英文别名: 3-hydroxy-1-phenylheptan-5-one；5-hydroxy-7-phenylheptan-3-one；3-Heptanone, 5-hydroxy-7-phenyl-
• CAS: 106353-51-9；69790-19-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: MDWSKRMCMKIOND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-7-苯基庚烷-3-酮 在 phosphorus pentoxide 作用下， 以 Petroleum ether 为溶剂， 生成 (E)-7-phenylhept-3-en-2-one
  参考文献：
  名称：

  Novel 7-phenylheptan-3-ones from the fungus Phellinus tremulae

  摘要：

  DOI：

  10.1016/s0031-9422(00)94676-4
• 作为产物：
  描述：

  3-hydroxy-N-methoxy-N-methyl-5-phenylpentanamide 在 palladium dichloride disodium hydrogenphosphate 、 氧气 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 6.0h， 生成 5-羟基-7-苯基庚烷-3-酮
  参考文献：
  名称：

  Oxidative Cyclization of β-Hydroxyenones with Palladium(II):  A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones

  摘要：

  A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.

  DOI：

  10.1021/ol0361296

文献信息

• Decarboxylative Aldol Reactions of Allyl β-Keto Esters via Heterobimetallic Catalysis
  作者：Sha Lou、John A. Westbrook、Scott E. Schaus

  DOI：10.1021/ja045981k

  日期：2004.9.1

  Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl beta-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl beta-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis

  涉及烯丙基β-酮酯的温和且选择性的杂双金属催化的脱羧醛醇反应已被开发。该反应在室温下由 Pd(0)-和 Yb(III)-DIOP 配合物促进，包括由烯丙基 β-酮酯原位形成酮烯醇化物，然后将烯醇化物加入醛。该反应是异双金属催化的一个新例子，其中优化的反应条件需要添加两种金属。
• Engineered Artificial Carboligases Facilitate Regioselective Preparation of Enantioenriched Aldol Adducts
  作者：Duncan S. Macdonald、Xavier Garrabou、Cindy Klaus、Rebecca Verez、Takahiro Mori、Donald Hilvert

  DOI：10.1021/jacs.0c02351

  日期：2020.6.10

  the binding and activation of specific aldol donors, as well as their subsequent reaction with diverse aldehyde acceptors. Broadening the substrate scope of this evolutionarily naïve catalyst proved much easier than previous attempts to redesign natural aldolases, suggesting that such proteins may be excellent starting points for the development of customized biocatalysts for diverse practical applications

  控制羟醛添加的区域和立体选择性通常具有挑战性。在这里，我们展示了对作为醛醇供体的丙酮具有高度特异性的人工醛缩酶可以通过单个活性位点突变重新设计，以接受具有显着效率、区域选择性和立体控制的线性和环状脂肪族酮。生化和晶体学数据显示突变的残基如何调节特定醛醇供体的结合和活化，以及它们随后与不同醛受体的反应。事实证明，扩大这种进化幼稚催化剂的底物范围比以前重新设计天然醛缩酶要容易得多，这表明此类蛋白质可能是开发用于各种实际应用的定制生物催化剂的极好起点。
• Reformatsky-type reaction of α-haloketones promoted by titanium tetraiodide
  作者：Makoto Shimizu、Fumiko Kobayashi、Ryuuichirou Hayakawa

  DOI：10.1016/s0040-4020(01)00982-6

  日期：2001.11

  Titanium(IV) tetraiodide induces a Reformatsky-type reaction of α-iodoketones with carbonyl compounds to give β-hydroxy ketones in good to high yields.

  四碘化钛（IV）引发α-碘酮与羰基化合物的Reformatsky型反应，从而以良好或高收率得到β-羟基酮。
• A novel 3,4-dihydropyrimidin-2(1H)-one: HIV-1 replication inhibitors with improved metabolic stability
  作者：Junwon Kim、Taedong Ok、Changmin Park、Wonyoung So、Mina Jo、Youngmi Kim、Minjung Seo、Doohyun Lee、Suyeon Jo、Yoonae Ko、Inhee Choi、Youngsam Park、Jaewan Yoon、Moon Kyeong Ju、JiYe Ahn、Junghwan Kim、Sung-Jun Han、Tae-Hee Kim、Jonathan Cechetto、Jiyoun Nam、Michel Liuzzi、Peter Sommer、Zaesung No

  DOI：10.1016/j.bmcl.2012.01.133

  日期：2012.4

  Following the previous SAR of a novel dihydropyrimidinone scaffold as HIV-1 replication inhibitors a detailed study directed towards optimizing the metabolic stability of the ester functional group in the dihydropyrimidinone (DHPM) scaffold is described. Replacement of the ester moiety by thiazole ring significantly improved the metabolic stability while retaining antiviral activity against HIV-1 replication. These novel and potent DHPMs with bioisosteres could serve as advanced leads for further optimization. (C) 2012 Elsevier Ltd. All rights reserved.