(4-phenylbutyl)magnesium bromide | 27152-04-1

• 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: (4-phenylbutyl)magnesium bromide
• 英文别名: 4-phenylbutylmagnesium bromide；phenbutylmagnesium bromide；(4-phenyl-butyl)-magnesium bromide
• CAS: 27152-04-1
• 化学式: C₁₀H₁₃BrMg
• 分子量: 237.422
• InChiKey: UOAWECHSENGIMF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (4-phenylbutyl)magnesium bromide 在 氢氧化钾 、 sodium acetate 、 四氯化锡 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 ethyl 7-oxo-7-[3-(5-phenylpentyl)thiophen-2-yl]heptanoate
  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：

  4-苯基-1-丁基溴 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (4-phenylbutyl)magnesium bromide
  参考文献：
  名称：

  Structure–Activity Relationship Studies of α-Ketoamides as Inhibitors of the Phospholipase A and Acyltransferase Enzyme Family

  摘要：

  The phospholipase A and acyltransferase (PLAAT) family of cysteine hydrolases consists of five members, which are involved in the Ca2+-independent production of N-acylphosphatidylethanolamines (NAPEs). NAPEs are lipid precursors for bioactive N-acylethanolamines (NAEs) that are involved in various physiological processes such as food intake, pain, inflammation, stress, and anxiety. Recently, we identified alpha-ketoamides as the first pan-active PLAAT inhibitor scaffold that reduced arachidonic acid levels in PLAAT3-overexpressing U2OS cells and in HepG2 cells. Here, we report the structure-activity relationships of the alpha-ketoamide series using activity-based protein profiling. This led to the identification of LEI-301, a nanomolar potent inhibitor for the PLAAT family members. LEI-301 reduced the NAE levels, including anandamide, in cells overexpressing PLAAT2 or PLAAT5. Collectively, LEI-301 may help to dissect the physiological role of the PLAATs.

  DOI：

  10.1021/acs.jmedchem.0c00522
• 作为试剂：
  描述：

  三氯乙醛 在 乙醚 、 (4-phenylbutyl)magnesium bromide 作用下， 生成 2,2,2-三氯乙醇
  参考文献：
  名称：

  The Action of Chloral on β-Phenylethylmagnesium Bromide, γ-Phenylpropylmagnesium Bromide and δ-Phenylbutylmagnesium Bromide

  摘要：

  DOI：

  10.1021/ja01293a042

文献信息

• Lariat ether alcohols based on dibenzo-16-crown-5
  作者：Richard A. Bartsch、Leah P. Bitalac、Charles L. Cowey、Sadik Elshani、Mi-Ja Goo、Vincent J. Huber、Sheryl N. Ivy、Youngchan Jang、Russell J. Johnson、Jong Seung Kim、Elzbieta Luboch、Joseph A. Mcdonough、Michael J. Pugia、Byungki Son、Qiang Zhao

  DOI：10.1002/jhet.5570370554

  日期：2000.9

  Synthetic routes to forty-four dibenzocrown ether alcohols are reported. The new crown ether com pounds are based on a sym-dibenzo-16-crown-5 platform. Most have a hydroxy group and an alkyl, aryl, aralkyl, alkenyl, alkynyl, or perfluoroalkyl group on the central carbon of the three-carbon bridge. Others have substituted benzene rings and either a hydroxy or -O(CH2)nOH group attached to the central

  据报道合成途径为四十四种二苯并冠醚醇。新的冠醚化合物基于sym -dibenzo-16-crown-5平台。大多数在三碳桥的中心碳上具有羟基和烷基，芳基，芳烷基，烯基，炔基或全氟烷基。其他的具有取代的苯环和与三碳桥的中心碳相连的羟基或-O（CH 2）n OH。
• Kinetics and mechanisms of cleavage of allylic derivatives of group IVA elements by mercuric salts
  作者：R.M.G Roberts

  DOI：10.1016/s0022-328x(00)85399-1

  日期：1969.8

  The cleavage of allylic derivatives of trialkyl-and triphenyltin compounds by mercuric salts in solvent ethanol has been examined using spectrophotometric and chromatographic techniques.

  已使用分光光度法和色谱技术检查了汞盐在溶剂乙醇中对三烷基锡和三苯基锡化合物的烯丙基衍生物的裂解。
• Iminyl Radical-Triggered Intermolecular Distal C(sp³)–H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade
  作者：Yu-Rui Gu、Xin-Hua Duan、Li Chen、Zhi-Yong Ma、Pin Gao、Li-Na Guo

  DOI：10.1021/acs.orglett.8b03865

  日期：2019.2.15

  An efficient iron-catalyzed intermolecular remote C(sp3)–H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

  通过亚胺基引发的1，5-氢原子转移（HAT）级联反应，开发了一种有效的铁催化的烷基酮的分子间远程C（sp 3）-H杂芳基化反应。该方案适用于多种烷基酮和杂芳基，因此为烷基酮和杂芳基的后期官能化提供了一种直接的方法。
• Asymmetric Catalytic Preparation of Polysubstituted Cyclopropanol and Cyclopropylamine Derivatives
  作者：Marwan Simaan、Ilan Marek

  DOI：10.1002/anie.201710707

  日期：2018.2.5

  cyclopropenes followed by either an electrophilic oxidation or amination reaction provides a unique approach to the formation of diastereomerically pure and enantiomerically enriched cyclopropanol and cyclopropylamine derivatives, respectively.

  环丙烯的催化不对称碳金属化，然后进行亲电氧化或胺化反应，为形成非对映体纯和对映体富集的环丙醇和环丙胺衍生物提供了独特的方法。
• Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes
  作者：Manuel Guisán-Ceinos、Victor Martín-Heras、Rita Soler-Yanes、Diego J. Cárdenas、Mariola Tortosa

  DOI：10.1039/c8cc03760d

  日期：——

  method to prepare enantiomerically enriched trisubstituted allenes using alkyl Grignard reagents and bench stable propargylic ammonium salts. Excellent yields as well as regio- and stereoselectivities are observed. Our conditions provide a solution to the allene racemization, which has been a long-standing problem when using Grignard reagents.

  在本文中，我们描述了使用烷基格氏试剂和台式稳定的炔丙基铵盐制备对映体富集的三取代的烯丙基的稳健而实用的方法。观察到优异的产率以及区域和立体选择性。我们的条件为丙二烯外消旋提供了解决方案，这在使用格氏试剂时一直是一个长期存在的问题。