1-苯基-3-(噻吩-3-基)丙烷-1-酮 | 71778-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-苯基-3-(噻吩-3-基)丙烷-1-酮
• 英文名称: 1-phenyl-3-(3-thienyl)-1-propanone
• 英文别名: 1-phenyl-3-(thiophen-3-yl)propan-1-one；2-(3'-Thienyl)-ethyl-phenylketon；1-Phenyl-3-thiophen-3-ylpropan-1-one
• CAS: 71778-01-3
• 化学式: C₁₃H₁₂OS
• 分子量: 216.304
• InChiKey: SZVFGAFSHDSJQB-UHFFFAOYSA-N

物化性质

• 熔点：
  49.5-50.0 °C(Solv: hexane (110-54-3))
• 沸点：
  180 °C(Press: 3 Torr)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-3-(噻吩-3-基)丙烷-1-酮 在 氢氧化钾 、 四氯化锡 、 一水合肼 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 9.0h， 生成 5-<3-(3-phenylpropyl)-2-thienyl>pentanoic acid
  参考文献：
  名称：

  .omega.-[(.omega.-Arylalkyl)thienyl]alkanoic acids: from specific LTA4 hydrolase inhibitors to LTB4 receptor antagonists

  摘要：

  A series of omega-[(omega-arylalkyl)thienyl]alkanoic acid isomers was prepared and a structure-activity relationship was investigated. These compounds have displayed either LTA, hydrolase inhibition activities or LTB4 receptor binding activities, or both, depending on the relative orientation of the two side chains on the thiophene ring. Whereas the 2,5-isomers specifically exhibited LTA4 hydrolase inhibition, 3,5-isomers displayed both activities. On the other hand, the ''ortho-isomers'' specifically inhibited the binding of the LTB4 to its receptor. The side-chain lengths were also important for an optimal inhibition or binding activity. Substitutions on the terminal aromatic ring or on the thiophene nucleus led to small changes in both activities. The most dramatic effect was obtained by substituting the carboxylic acid side chain in the alpha-position with one or two methyl groups, which substantially enhanced the LTB4 receptor binding activity. In the most favorable case, the alpha,alpha-dimethyl derivative RP66153 was found 20-fold more potent than its linear counterpart.

  DOI：

  10.1021/jm00095a011
• 作为产物：
  描述：

  生成 1-苯基-3-(噻吩-3-基)丙烷-1-酮
  参考文献：
  名称：

  Cobalt-Catalyzed Intermolecular Hydroacylation of Olefins through Chelation-Assisted Imidoyl C–H Activation

  摘要：

  A low-valent cobalt catalyst generated from cobalt(II) bromide, a diphosphine ligand, and zinc powder promotes intermolecular hydroacylation of olefins using N-3-picolin-2-yl aldimines as aldehyde equivalents, which affords, upon acidic hydrolysis, ketone products in moderate to good yields with high linear selectivity. The reaction is applicable to styrenes, vinylsilanes, and aliphatic olefins as well as to various aryl and heteroaryl aldimines. The cobalt catalysis features a distinctively lower reaction temperature (60 degrees C) compared with those required for the same type of transformations catalyzed by rhodium complexes (typically 130-150 degrees C).

  DOI：

  10.1021/acscatal.5b00581

文献信息

• Rhodium(I)-Catalyzed Arylation of β-Chloro Ketones and Related Derivatives through Domino Dehydrochlorination/ Conjugate Addition
  作者：Quanbin Jiang、Tenglong Guo、Qingfu Wang、Ping Wu、Zhengkun Yu

  DOI：10.1002/adsc.201200821

  日期：2013.6.17

  Highly efficient arylations of β‐chloro ketones and their ester and amide derivatives were achieved by means of domino dehydrochlorination/Rh(I)‐catalyzed conjugate addition. In situ generated vinyl ketones and their analogues were identified as the reaction intermediates. The present synthetic protocol provides a concise route to (chiral) β‐aryl ketones, esters, and amides.

  β-氯酮及其酯和酰胺衍生物的高效芳基化是通过多米诺脱氢/ Rh（I）催化的共轭物加成反应实现的。原位生成的乙烯基酮及其类似物被鉴定为反应中间体。本合成方案为（手性）β-芳基酮，酯和酰胺提供了一条简明的途径。
• Methanol as a hydrogen source: room-temperature highly-selective transfer hydrogenation of α,β-unsaturated ketones
  作者：Nidhi Garg、Hari Prasaad Somasundharam、Pardeep Dahiya、Basker Sundararaju

  DOI：10.1039/d2cc03597a

  日期：——

  The described system offers an ideal, user-friendly protocol for the chemoselective homogeneous hydrogenation of α,β-unsaturated ketones at room temperature using methanol as a liquid organic hydrogen carrier. Excellent yields were achieved with an in situ-prepared phosphine-free Cp*Ir(III)/bipyridonate complex. Chemoselective reduction with other reducible functionalities and late-stage functionalization

  所描述的系统为使用甲醇作为液态有机氢载体在室温下对α、β-不饱和酮进行化学选择性均相氢化提供了一种理想的、用户友好的协议。使用原位制备的无膦Cp*Ir( III )/联吡啶络合物获得了优异的产率。还探索了具有其他可还原功能和后期功能化的化学选择性还原。
• TAMARU Y.; YAMADA Y.; YOSHIDA Z., TETRAHEDRON, 1979, 35, NO 3, 329-340
  作者：TAMARU Y.、 YAMADA Y.、 YOSHIDA Z.

  DOI：——

  日期：——
• .omega.-[(.omega.-Arylalkyl)thienyl]alkanoic acids: from specific LTA4 hydrolase inhibitors to LTB4 receptor antagonists
  作者：Richard Labaudiniere、Gerd Hilboll、Alicia Leon-Lomeli、Bernard Terlain、Francoise Cavy、Michael Parnham、Peter Kuhl、Norbert Dereu

  DOI：10.1021/jm00095a011

  日期：1992.8

  A series of omega-[(omega-arylalkyl)thienyl]alkanoic acid isomers was prepared and a structure-activity relationship was investigated. These compounds have displayed either LTA, hydrolase inhibition activities or LTB4 receptor binding activities, or both, depending on the relative orientation of the two side chains on the thiophene ring. Whereas the 2,5-isomers specifically exhibited LTA4 hydrolase inhibition, 3,5-isomers displayed both activities. On the other hand, the ''ortho-isomers'' specifically inhibited the binding of the LTB4 to its receptor. The side-chain lengths were also important for an optimal inhibition or binding activity. Substitutions on the terminal aromatic ring or on the thiophene nucleus led to small changes in both activities. The most dramatic effect was obtained by substituting the carboxylic acid side chain in the alpha-position with one or two methyl groups, which substantially enhanced the LTB4 receptor binding activity. In the most favorable case, the alpha,alpha-dimethyl derivative RP66153 was found 20-fold more potent than its linear counterpart.
• Cobalt-Catalyzed Intermolecular Hydroacylation of Olefins through Chelation-Assisted Imidoyl C–H Activation
  作者：Junfeng Yang、Yuan Wah Seto、Naohiko Yoshikai

  DOI：10.1021/acscatal.5b00581

  日期：2015.5.1

  A low-valent cobalt catalyst generated from cobalt(II) bromide, a diphosphine ligand, and zinc powder promotes intermolecular hydroacylation of olefins using N-3-picolin-2-yl aldimines as aldehyde equivalents, which affords, upon acidic hydrolysis, ketone products in moderate to good yields with high linear selectivity. The reaction is applicable to styrenes, vinylsilanes, and aliphatic olefins as well as to various aryl and heteroaryl aldimines. The cobalt catalysis features a distinctively lower reaction temperature (60 degrees C) compared with those required for the same type of transformations catalyzed by rhodium complexes (typically 130-150 degrees C).