3-异丙氧基-1-苯基-1-丙酮 | 85670-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-异丙氧基-1-苯基-1-丙酮
• 英文名称: 3-isopropoxy-1-phenylpropan-1-one
• 英文别名: 3-isopropoxy-1-phenyl-1-propanone；1-Phenyl-3-propan-2-yloxypropan-1-one
• CAS: 85670-60-6
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: XCOLZHTYXZKPHW-UHFFFAOYSA-N

物化性质

• 沸点：
  284.4±23.0 °C(Predicted)
• 密度：
  1.0108 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-异丙氧基-1-苯基-1-丙酮 在 对甲苯磺酸 作用下， 以 乙醚 、 2,2,2-三氟乙醇 为溶剂， 反应 13.25h， 生成 (+/-)-3-phenyl-1-pentanol
  参考文献：
  名称：

  烷基醚在布朗斯台德酸催化的分子内氢原子转移中作为无痕氢化物供体

  摘要：

  已经开发了在布朗斯台德酸催化下醇的脱氧和烯烃的氢化的新方案。该方法基于使用苄基或异丙基醚作为无痕氢原子供体，并且涉及分子内氢化物转移作为关键步骤，这是通过区域和立体选择性方式实现的。

  DOI：

  10.1002/anie.201801953
• 作为产物：
  描述：

  苯乙酮 在 sodium carbonate 、 三氟乙酸 、 diisopropylammonium trifluoroacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 3-异丙氧基-1-苯基-1-丙酮
  参考文献：
  名称：

  Oxa-Michael addition promoted by the aqueous sodium carbonate

  摘要：

  An efficient Michael addition of alcohols to activated alkenes promoted by sodium carbonate with water as reaction medium has been developed. The reaction provides a general, economical and environmentally friendly approach for the synthesis of beta-alkoxycarbonyl compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.019

文献信息

• Additive‐Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst
  作者：Brian Spiegelberg、Andrea Dell'Acqua、Tian Xia、Anke Spannenberg、Sergey Tin、Sandra Hinze、Johannes G. de Vries

  DOI：10.1002/chem.201901148

  日期：2019.6.12

  Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base

  通过在不存在任何添加剂的情况下使用空气和湿气稳定的钴（II）配合物，可以实现烯丙醇在乙醇中的催化异构化（绿色溶剂）。在温和的条件下，被磷原子上的苯基取代的钴PNP钳形络合物似乎是活性最高的。即使加入一当量的碱可大大提高反应速度，但在120°C时仍可获得较高的反应速率。尽管获得了支持脱氢-加氢机理的一些证据，但已证明这不是主要机理。取而代之的是，乙醇脱氢形成的氢化钴配合物能够通过烯烃插入-消除反应实现双键异构化。
• Cu-Catalyzed Sequential Dehydrogenation–Conjugate Addition for β-Functionalization of Saturated Ketones: Scope and Mechanism
  作者：Xiaoming Jie、Yaping Shang、Xiaofeng Zhang、Weiping Su

  DOI：10.1021/jacs.6b01337

  日期：2016.5.4

  The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible

  报道了第一个铜催化的饱和酮直接β-官能化。该协议使不同的酮能够在操作简单的条件下以通常良好的产率与广泛的氮、氧和碳亲核试剂结合。进行了详细的机理研究，包括动力学研究、KIE 测量、反应中间体的鉴定、EPR 和紫外可见实验，结果表明该反应是通过一种新型的基于自由基的脱氢生成烯酮和随后的共轭加成序列进行的。
• [EN] CATALYSTS<br/>[FR] CATALYSEURS
  申请人：GOLDENKEYS HIGH TECH MAT CO LTD

  公开号：WO2020240178A1

  公开（公告）日：2020-12-03

  A compound, e.g. a diamine ligand, represented by the following general formula (1): (Formula (1)) wherein each * represents an asymmetric carbon atom; X represents a group selected from one of an ester (e.g. a t-butyl ester); a thioester; an amide; a heterocyclic moiety (e.g. a five-membered heterocyclic ring) comprising one or more of O, S, Se, and/or P (e.g. a furan, a tetrahydrofuran, a thiophene, an isoxazole, a bromo-furan, or a thiazole); a moiety (e.g. a five-membered heterocyclic ring) comprising a nitrogen atom, wherein the nitrogen atom is protected with a protecting group containing an electron-withdrawing group, preferably the protecting group is selected from one of a carbamate protecting group, an amide protecting group, an aryl sulphonamide protecting group, or an alkyl sulphonamide protecting group; and optionally X may additionally comprise a solid support, e.g. a polymeric or a silica particle; Y represents or is CtT'T'' where 't' is 0 or 1 and when 't' is 1 T' and T'' may individually represent a substituent, e.g. if t is 1, T' and/or T'' may each be hydrogen or deuterium atom, or a halogen atom; for example, Y may represent a carbon atom comprising two further substituents; Z represents a hydrogen atom or a deuterium atom; R1 represents an alkyl group (e.g. a functionalised alkyl group) preferably having between 1 to 100 carbon atoms, for example, between 1 to 30 carbon atoms (e.g. 1 to 20 carbon atoms, or 1 to 10 carbon atoms), a halogenated alkyl group preferably having between 1 to 100 carbon atoms (e.g. CF3), for example, between 1 to 30 carbon atoms (e.g. 1 to 20 carbon atoms, or 1 to 10 carbon atoms), an aryl group preferably having between 5 to 100 carbon atoms, e.g. 6 to 30 carbon atoms and optionally having one or more substituents selected from alkyl groups preferably having 1 to 100 carbon atoms, e.g. 1 to 10 carbon atoms, halogenated alkyl groups preferably having 1 to 100 carbon atoms, e.g. 1 to 10 carbon atoms, and/or halogen atoms; or R1 represents a solid support, e.g. a silica particle or a polymeric particle; R2 and R3 each independently represent a group selected from alkyl groups preferably having between 1 to 100 carbon atoms, for example 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), aryl groups (e.g. phenyl groups), and cycloalkyl groups preferably having 3 to 8 carbon atoms, the aryl group or phenyl group optionally having one or more substituents selected from alkyl groups preferably having between 1 to 100 carbon atoms, e.g. between 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), alkoxy groups preferably having between 1 to 100 carbon atoms, for example, between 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), and halogen atoms, and each hydrogen atom of the cycloalkyl groups being optionally replaced by an alkyl group preferably having between 1 to 100 carbon atoms, e.g. 1 to 20 carbon atoms (e.g. 1 to 10 carbon atoms), or R1 represents a polyethylene glycol (PEG) moiety having the formula C2nH4n+2On+1 wherein n is an integer between 1 and 100; or R2 and R3 form a ring together with carbon atoms to which R2 and R3 are bonded; R4 represents a hydrogen atom or a deuterium atom.

  一个化合物，例如一种二胺配体，由以下一般式（1）表示：（公式（1））其中每个*代表一个不对称碳原子；X代表从酯（例如叔丁基酯）中选择的一个基团；硫酯；酰胺；一个杂环基团（例如一个含有O、S、Se和/或P的五元杂环环）；一个含有氮原子的基团，其中氮原子被含有电子吸引基团的保护基团保护，优选的保护基团从碳酸酯保护基团、酰胺保护基团、芳基磺酰胺保护基团或烷基磺酰胺保护基团中选择；可选地，X还可以包括固体支撑，例如聚合物或二氧化硅颗粒；Y代表或是CtT'T''，其中't'为0或1，当't'为1时，T'和T''可以分别代表一个取代基，例如，如果t为1，T'和/或T''可以分别是氢或氘原子，或卤原子；例如，Y可以代表一个包含两个进一步取代基的碳原子；Z代表氢原子或氘原子；R1代表一个烷基基团（例如，一个官能化烷基基团），优选地具有1到100个碳原子，例如，具有1到30个碳原子（例如，1到20个碳原子，或1到10个碳原子），一种卤代烷基基团，优选地具有1到100个碳原子（例如CF3），例如，具有1到30个碳原子（例如，1到20个碳原子，或1到10个碳原子），一种芳基基团，优选地具有5到100个碳原子，例如6到30个碳原子，并且可选地具有一个或多个取代基，所述取代基从烷基基团中选择，优选地具有1到100个碳原子，例如，1到10个碳原子，卤代烷基基团，优选地具有1到100个碳原子，例如，1到10个碳原子，和/或卤原子；或R1代表固体支撑，例如二氧化硅颗粒或聚合物颗粒；R2和R3各自独立地代表从烷基基团中选择的一个基团，优选地具有1到100个碳原子，例如1到20个碳原子（例如1到10个碳原子），芳基基团（例如苯基基团）和环烷基基团，优选地具有3到8个碳原子，所述芳基基团或苯基基团可选地具有一个或多个取代基，所述取代基从烷基基团中选择，优选地具有1到100个碳原子，例如，1到20个碳原子（例如，1到10个碳原子），烷氧基基团，优选地具有1到100个碳原子，例如，1到20个碳原子（例如，1到10个碳原子），和卤原子，所述环烷基基团的每个氢原子可选地被烷基基团替换，优选地具有1到100个碳原子，例如，1到20个碳原子（例如，1到10个碳原子），或R1代表具有公式C2nH4n+2On+1的聚乙二醇（PEG）基团，其中n是1到100之间的整数；或R2和R3与R2和R3结合的碳原子一起形成一个环；R4代表氢原子或氘原子。
• Probing the Effects of Heterocyclic Functionality in [(Benzene)Ru(TsDPENR)Cl] Catalysts for Asymmetric Transfer Hydrogenation
  作者：Jonathan Barrios-Rivera、Yingjian Xu、Martin Wills

  DOI：10.1021/acs.orglett.9b02339

  日期：2019.9.20

  the amine nitrogen atom were prepared and evaluated in the asymmetric transfer hydrogenation of ketones. Bidentate and tridentate ligands demonstrated a mutual exclusivity directly related to their function as catalysts. A broad series of ketones were reduced with these new catalysts, permitting the ready identification of an optimal catalyst for each substrate and revealing the subtle effects that changes

  制备了一系列在胺氮原子上含有杂环基的TsDPEN催化剂，并在酮的不对称转移加氢中进行了评估。二齿和三齿配体表现出相互排他性，与它们作为催化剂的功能直接相关。这些新型催化剂可还原大量的酮，从而可以迅速确定每种底物的最佳催化剂，并揭示出附近施主基团变化所表现出的微妙效果。
• REACTIONS OF α-HETEROATOM-SUBSTITUTED ETHERS AND SULFIDES WITH SILYL ENOL ETHERS. CHEMOSELECTIVITY IN THE CLEAVAGE OF HETEROATOM–CARBON BONDS BY IODOTRIMETHYLSILANE AND TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
  作者：Akira Hosomi、Yasuyuki Sakata、Hideki Sakurai

  DOI：10.1246/cl.1983.405

  日期：1983.3.5

  Reactions of α-heteroatom-substituted ethers and related compounds (R1R2CXY; X, Y = RO, RS and Cl) with silyl enol ethers and ketene silyl acetals took place in the presence of iodotrimethylsilane (Ia) and trimethylsilyl triflate (Ib) as a catalyst and factors influencing the activation of the heteroatom by I were examined.

  α-杂原子取代的醚和相关化合物（R1R2CXY；X，Y = RO，RS 和 Cl）与甲硅烷基烯醇醚和烯酮甲硅烷基缩醛的反应发生在碘三甲基硅烷 (Ia) 和三甲基甲硅烷基三氟甲磺酸酯 (Ib) 作为检查了催化剂和影响 I 对杂原子活化的因素。