1-lithio-3-phenylpropane | 64740-46-1

• 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: 1-lithio-3-phenylpropane
• 英文别名: 3-phenylpropyl lithium
• CAS: 64740-46-1
• 化学式: C₉H₁₁Li
• 分子量: 126.127
• InChiKey: HNKORHQVHAXMPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-lithio-3-phenylpropane 在 benzoic-acid-d1 、 苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.51h， 生成 苯戊酮
  参考文献：
  名称：

  The reaction ofn-butyllithium with benzoic acid: is nucleophilic addition competitive with deprotonation?

  摘要：

  An evaluation of a branching vs sequential mechanism for the reaction of benzoic acid with n-butyllithium favors the latter. (C) 1997 by John Whey & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199707)10:7<537::aid-poc910>3.0.co;2-y
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 生成 1-lithio-3-phenylpropane
  参考文献：
  名称：

  α-(甲硫基)乙烯基铜酸盐和α-(氨基甲酰氧基)烷基硼酸盐之间的类胡萝卜素消除交叉偶联对映控制联烯的合成

  摘要：

  丙二烯（R 1 R 2 C=C=CHR 3，R 1 = 芳基/烷基，R 2，R 3 = 烷基）的简便对映控制合成基于几何纯高分子之间的卡宾消除交叉偶联 (CEX C ) 进行了描述-order α-(甲硫基)乙烯基铜酸盐，通过硫代炔烃的碳化铜化原位生成（然后通过添加n -BuLi活化）和富含对映体的 α-（氨基甲酰氧基）烷基硼酸盐（15 个实例，30-78% 产率，15-95% ee ). 该 CEX C过程的立体化学保真度依赖于底物，这种现象暂时归因于推定的有机铜介导的丙二烯外消旋化途径。

  DOI：

  10.1055/a-2072-2882
• 作为试剂：
  描述：

  N-Deutero-N-ethyl-o-bromobenzamide 在 叔丁基锂 、 1-lithio-3-phenylpropane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 N-乙苯甲醯胺
  参考文献：
  名称：

  Selectivities in reactions of organolithium reagents with aryl bromides which bear proton-donating groups

  摘要：

  Studies of substrates which offer an acidic hydrogen and an aryl bromide for reaction with an organolithium reagent have been carried out with a series of benzene bromo amides and bromo anilides as well as selected benzene bromo carboxylic acids, bromoanilines, and bromobenzylamines. A representative example is the reaction of N-ethyl-N-deutero-o-bromobenzamide (6-d) with 1-lithio-3-phenylpropane to give N-ethyl-o-deuterobenzamide (46%, 94%-d) (7-d), N-ethyl-o-bromobenzamide (6)(49%), 3-deutero-1-phenylpropane(51%, 92%-d), and 1-bromo-3-phenylpropane (48%). Product formation in this and related cases is explained by the operation of a two step sequence in which an initial deprotonation is followed by a bromine-lithium exchange which is accelerated with respect to mixing. Such a sequence is consistent with the results of deuterium labeling and with changes in product ratios on different mixing and with differently aggregated organolithium reagents. Support is provided for the operation of two pathways for the expedited bromine-lithium exchange reactions. In one pathway a high local concentration of the organolithium reagent promotes rapid reaction and in the second the exchange reaction occurs within an initially formed complex. The selectivity for removal of a bromine ortho to a lithiated carboxamide is found to be 5-8 with n-butyllithium, and satisfactory synthetic ortho selectivity is obtained for N-ethyl-2,5-dibromobenzamide with phenyllithium.

  DOI：

  10.1021/jo00078a007

文献信息

• Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
  申请人：Dow AgroSciences LLC

  公开号：US06355660B1

  公开（公告）日：2002-03-12

  A compound having the following formula: wherein R3 and M are defined herein, and processes therewith.

  具有以下公式的化合物： 其中R3和M的定义如本文所述，以及与此相关的过程。
• Reaction of 1-arylpropenyl-lithium with t-alkyl bromides. The influence of substituent electronic effects and additives on the course of the reaction
  作者：Jiro Tanaka、Masatomo Nojima、Shigekazu Kusabayashi

  DOI：10.1039/c39860000242

  日期：——

  The reaction of 1-arylpropenyl-lithium (1a–c) with t-alkyl bromides proceeds by either a nucleophilic substitution or single electron transfer mechanism, the preferred pathway being a function of electronic substituent effects and the absence or presence of tetramethylethylenediamine or hexamethylphosphoramide.

  1-芳基丙烯基锂（1a–c）与叔烷基溴的反应是通过亲核取代或单电子转移机制进行的，优选的途径是电子取代基效应的作用以及是否存在四甲基乙二胺或六甲基磷酰胺。
• A Cu-mediated one-pot Michael addition/α-arylation strategy using a diaryliodonium salt: a direct and efficient approach to α-aryl-β-substituted cyclic ketone scaffolds
  作者：Jin-Long Pan、Tao Chen、Zhi-Qiang Zhang、Yi-Fan Li、Xiao-Ming Zhang、Fu-Min Zhang

  DOI：10.1039/c5cc09837h

  日期：——

  A direct and efficient construction of [small alpha]-aryl-[small beta]-substituted cyclic ketone scaffolds has been achieved using Cu-mediated one-pot Michael addition/[small alpha]-arylation strategy. The reaction features easily available materials, broad substrate scope, moderate to...

  使用Cu介导的一锅迈克尔加成/ [小α-芳基化]策略已经实现了直接和有效构建小[α]-芳基-[小β]取代的环酮支架的方法。该反应具有易于获得的材料，广泛的底物范围，中等至...
• Dihydropyridines in Organometallic Synthesis. Formation of Pyridine and Dihydropyridine-Stabilized Alkylidene Complexes of Tungsten(0) and Chromium(0) from Fischer Carbene Complexes:  Structure and Reactivity
  作者：Henri Rudler、Max Audouin、Andrée Parlier、Blanca Martin-Vaca、Régis Goumont、Thomas Durand-Réville、Jacqueline Vaissermann

  DOI：10.1021/ja9622057

  日期：1996.1.1

  1,2- and 1,4-dihydropyridines react with alkoxycarbene complexes of chromium and tungsten to give, upon an unprecedented hydride transfer, alcohol elimination, and pyridine fixation on the carbene carbon, a new class of air-stable pyridinium ylide complexes. These pyridine-protected alkylidene complexes of chromium(0) and tungsten(0) were fully characterized by X-ray crystallography. In the case of

  1,2- 和 1,4- 二氢吡啶与铬和钨的烷氧基卡宾配合物反应，通过前所未有的氢化物转移、醇消除和吡啶固定在卡宾碳上，产生一类新的空气稳定的吡啶鎓叶立德配合物。这些吡啶保护的铬 (0) 和钨 (0) 亚烷基配合物通过 X 射线晶体学进行了充分表征。在 (CO)5WC(CH3)(OEt) (5a) 的情况下，除了吡啶鎓叶立德配合物 (CO)5W-−C(H)( )(吡啶)+ (7a) 外，二氢吡啶鎓配合物 (CO) 5W--C(H)( )(2,5-二氢吡啶)+(8a)也被分离。中间体钨酸盐 (CO)5W--C(H)( )(OEt)( NC5H5)+ 可以通过使用 N-甲基二氢吡啶作为还原剂很容易地获得和表征。而苯基取代的吡啶鎓配合物很容易将亚苄基部分转移到烯烃上，烷基取代的配合物似乎更不愿意进行这种转移：在亲核烯烃如烯醇醚的情况下观察到令人满意的结果。如何...
• Enantioselective Inverse Electron Demand (3 + 2) Cycloaddition of Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand
  作者：Yin Zheng、Tianzhu Qin、Weiwei Zi

  DOI：10.1021/jacs.0c11504

  日期：2021.1.20

  Cycloaddition reactions between oxyallyl cations and alkenes are important transformations for the construction of ring systems. Although (4 + 3) cycloaddition reactions of oxyallyl cations are well-developed, (3 + 2) cycloadditions remain rare, and an asymmetric version has not yet been developed. Moreover, because oxyallyl cations are highly electrophilic, only electron-rich olefins can be used as

  氧烯丙基阳离子和烯烃之间的环加成反应是构建环系的重要转化。尽管氧烯丙基阳离子的 (4 + 3) 环加成反应很发达，但 (3 + 2) 环加成反应仍然很少，并且尚未开发出不对称版本。此外，由于氧烯丙基阳离子具有高度亲电性，因此只有富电子烯烃才能用作环加成伙伴。我们在此报告了一种钯-氧烯丙基物种与缺电子硝基烯烃之间的对映选择性 (3 + 2) 环加成反应的方法。这种转变是通过合理设计的氢键供体配体（FeUrPhos）实现的，并通过逆电子需求途径进行。使用这种方法，