3-oxopentan-2-yl benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-oxopentan-2-yl benzoate
• 英文别名: (2R)-2-(benzoyloxy)-3-Pentanone
• 化学式: C₁₂H₁₄O₃
• mdl: MFCD24391519
• 分子量: 206.241
• InChiKey: WENOPEBWFIDEKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-N-methyl-O-benzoyl-hydroxylamine 在 盐酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 3-oxopentan-2-yl benzoate
  参考文献：
  名称：

  A General Method for the α-Acyloxylation of Carbonyl Compounds

  摘要：

  A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.

  DOI：

  10.1021/ol052474e

文献信息

• 1,2-Dibromoethane and KI mediated α-acyloxylation of ketones with carboxylic acids
  作者：Xujie Wang、Gangsheng Li、Yanan Yang、Jianshuang Jiang、Ziming Feng、Peicheng Zhang

  DOI：10.1016/j.cclet.2019.08.052

  日期：2020.3

  Abstract The 1,2-dibromoethane- and KI-mediated α-acyloxylation of ketones is reported in moderate to good yield without the use of transition metals and strong oxidants. Various acids are well tolerated with wide functional group compatibility. An 1,2-dibromoethane- and KI-catalysed reaction mechanism is proposed based on the results of control experiments.

  摘要据报道，在不使用过渡金属和强氧化剂的情况下，酮的1,2-二溴乙烷和KI介导的α-酰氧基化反应具有中等至良好的收率。各种酸均具有良好的耐受性，并具有广泛的官能团相容性。根据控制实验结果，提出了1,2-二溴乙烷和KI催化的反应机理。
• Process for total synthesis of pladienolide B and pladienolide D
  申请人：Kanada Mikie Regina

  公开号：US20080021226A1

  公开（公告）日：2008-01-24

  [Problems to be Solved] To provide an effective process for total synthesis of pladienolide B and pladienolide D having excellent anti-tumor activity and to provide useful intermediates in the above-described process. [Measure for Solving the Problem] A process for producing a compound represented by Formula (11): wherein P 1 , P 7 , P 8 , P 9 and R 1 are the same as defined below, characterized by including reacting a compound represented by Formula (12): wherein P 7 means a hydrogen atom or a protecting group for hydroxy group; R 1 means a hydrogen atom or a hydroxy group, with a compound represented by Formula (13): wherein P 1 means a hydrogen atom or a protecting group for hydroxy group; P 8 means a hydrogen atom, an acetyl group or a protecting group for hydroxy group; P 9 means a hydrogen atom or a protecting group for hydroxy group; or P 8 and P 9 may form together a group represented by a formula: wherein R 5 means a phenyl group which may have a substituent, in the presence of a catalyst.

  解决的问题：提供一种有效的全合成过程，用于合成具有出色抗肿瘤活性的pladienolide B和pladienolide D，并在上述过程中提供有用的中间体。 解决问题的措施：一种制备由下式（11）表示的化合物的方法： 其中P1、P7、P8、P9和R1如下定义，其特征在于包括将由下式（12）表示的化合物与由下式（13）表示的化合物在催化剂存在下反应： 其中P7表示氢原子或羟基的保护基团；R1表示氢原子或羟基； 其中P1表示氢原子或羟基的保护基团；P8表示氢原子、乙酰基团或羟基的保护基团；P9表示氢原子或羟基的保护基团；或P8和P9可共同形成下式所示的基团： 其中R5表示可能具有取代基的苯基。
• PROCESS FOR TOTAL SYNTHESIS OF PLADIENOLIDE B AND PLADIENOLIDE D
  申请人：KANADA Regina Mikie

  公开号：US20100204490A1

  公开（公告）日：2010-08-12

  Process for producing compound of Formula: wherein P 2 , P 3 and R 2 are the same as defined below, characterized by comprising reacting a compound represented by Formula (7): wherein P 3 means a protecting group for hydroxy group; and Het means a 1-phenyl-1H-tetrazol-5-yl group, with a compound represented by Formula (8): wherein P 2 means a protecting group for hydroxy group; and R 2 means a phenyl group which may be substituted, in the presence of a base.

  生产式子为：其中P2、P3和R2的定义如下，其特征在于通过将式子（7）所代表的化合物与式子（8）所代表的化合物在碱存在下反应，其中P3代表羟基的保护基；Het代表1-苯基-1H-四唑-5-基基团，P2代表羟基的保护基；R2代表苯基，可以被取代。
• α-Acyloxylation of Ketones/Cyclic Ethers Mediated by Hypervalent Iodine(III) Reagents as Oxidants and Nucleophilic Sources
  作者：Hao Jia、Nan Li、Chunmei Tang、Wenjing Ni、Xinru Zhao、Jing Sun、Fufang Wu、Xiaobao Shen、Hongbin Zhai

  DOI：10.1021/acs.joc.3c02526

  日期：2024.2.2

  This study describes a catalyst-free α-acyloxylation of ketones and a KBr-mediated α-acyloxylation of cyclic ethers. These conversions are effectively mediated by hypervalent iodine(III) reagents serving dual roles as the oxidant and nucleophilic source. Consequently, esters are produced directly in moderate to excellent yields. The proposed method features good functional group compatibility, a broad

  本研究描述了酮的无催化剂 α-酰氧基化和 KBr 介导的环醚 α-酰氧基化。这些转化由具有氧化剂和亲核源双重作用的高价碘 (III) 试剂有效介导。因此，可以直接以中等至优异的产率生产酯。该方法具有官能团兼容性好、底物范围广、合成效率高、环境友好等特点。
• TOTAL SYNTHESIS OF PLADIENOLIDE B AND PLADIENOLIDE D
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1935893A1

  公开（公告）日：2008-06-25

  Disclosed is a process for production of a compound represented by the formula (11): [wherein P1 represents a hydrogen atom or a protective group for a hydroxyl group; P7 represents a hydrogen atom or a protective group for a hydroxyl group; P8 represents a hydrogen atom, an acetyl group or a protective group for a hydroxyl group and P9 represents a hydrogen atom or a protective group for a hydroxyl group, or P8 and P9 may together form a group represented by the formula: (where R5 represetns a phenyl group which may have a halogen atom; and R1 represetns a hydrogen atom or a hydroxyl group)]. The process comprises the step of reacting a compound represented by the formula (12): (wherein P7 and R1 are as defined above) with a compound represented by the formula (13): (wherein P1, P8, P9 and R5 are as defined above) in the presence of a catalyst.

  本发明公开了一种由式（11）代表的化合物的生产工艺： [其中 P1 代表氢原子或羟基的保护基团；P7 代表氢原子或羟基的保护基团；P8 代表氢原子、乙酰基或羟基的保护基团，P9 代表氢原子或羟基的保护基团，或 P8 和 P9 可共同形成由式（11）表示的基团： (其中 R5 代表苯基，该苯基可带有卤素原子；R1 代表氢原子或羟基）]。该工艺包括使式（12）所代表的化合物发生反应的步骤： (其中 P7 和 R1 如上定义）与式（13）所代表的化合物反应： (其中 P1、P8、P9 和 R5 如上定义）的化合物在催化剂存在下进行反应。