lithium,butylbenzene | 10104-42-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: lithium,butylbenzene
• 英文别名: 4-butylphenyllithium
• CAS: 10104-42-4
• 化学式: C₁₀H₁₃Li
• 分子量: 140.154
• InChiKey: SEVZJBPKDJZGFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 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：

  lithium,butylbenzene 在 N-氯代丁二酰亚胺 、 正丁基锂 、 二氧化硫 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 3.0h， 生成 5-[(4-Butylphenyl)-trimethylsilyloxymethyl]thiophene-3-sulfonyl chloride
  参考文献：
  名称：

  5-Substituted 3-thiophenesulfonamides as carbonic anhydrase inhibitors

  摘要：

  A series of 5-substituted 3-thiophenesulfonamides was prepared from 4-bromo-2-thiophene carboxaldehyde. Several of these compounds inhibited carbonic anhydrase II in vitro at concentrations of less than 10 nM. In the ex vivo assay, these compounds have inhibitory values in the 25-81% range. Additionally, none of these compounds exhibit sensitization potential as determined by in vitro measurement of cysteine reactivity.

  DOI：

  10.1016/0223-5234(96)89133-1
• 作为产物：
  描述：

  对丁基溴苯 在 叔丁基锂 作用下， 以 正戊烷 为溶剂， 反应 72.0h， 生成 lithium,butylbenzene
  参考文献：
  名称：

  Synthesis and Characterization of Lewis Base-Free, σ-Bonded Lithium Aryls:  A Structural Model for Unsolvated Phenyllithium in the Solid State

  摘要：

  The synthesis and characterization of four Lewis base-free, sigma-bonded lithium aryls are reported. This work was undertaken in order to provide a model for the solid-state structure of phenyllithium, which is currently unknown. Nondonor hydrocarbon solubility of the four lithium aryls (LiC6H3-3,5-t-Bu(2))(6) (1), (LiC6H4-4-t-Bu)(n) (2), (LiC6H4-4-n-Bu)(n) (3), and {LiC6H4-4-SiMe(2)(t-Bu)}(n) (4) was achieved by the incorporation of meta- or para-substituents on the aryl rings. This permitted C-13 NMR spectroscopy and crystal growth using their solutions. It is proposed that the absence of bulky ortho-substituents allows association of the Lithium aryls to occur in a manner similar to that of phenyllithium itself. The C-13 NMR data for the ipso-carbon atoms suggest an association number of at least four or, more probably, six in solution. These data are in agreement with the X-ray crystal structure of 1, which is hexameric, with a distorted octahedral (trigonal antiprismatic) array of lithium ions. Six of the eight Lis faces are capped by an aryl group that interacts primarily through the C(ipso) atom. Weaker Li-C(ortho) interactions are also apparent. This structure is the first of this type for an unsolvated, sigma-bonded Lithium aryl. Crystal data with Cu K alpha (lambda = 1.541 78 Angstrom) radiation for 1 at 130 K: 1, C84H126Li6, M = 1177.49, a = 13.516(2) Angstrom, b = 15.124(3) Angstrom, c = 20.958(3) Angstrom, alpha = 84.084(13)degrees, beta = 86.249(11) Angstrom, gamma = 68.675(13)degrees, V = 3967.7(11) Angstrom(3), Z = 2, space group , R(1) = 0.085 for 7983 (I > 2 sigma(I)) data.

  DOI：

  10.1021/ja962889i

文献信息

• <i>P</i>-Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions
  作者：Zhenjie Gan、Mengna Zhi、Ruiping Han、Er-Qing Li、Zheng Duan、François Mathey

  DOI：10.1021/acs.orglett.9b00734

  日期：2019.4.19

  synthesized and used in the copper(I)-catalyzed enatioselective [3 + 2] cycloaddition of iminoesters with alkenes. A variety of highly functionalized pyrrolidines were obtained in excellent yield and enatioselectivity. This is the first example of a pair of P-stereogenic ligands working as pseudoenantiomers to tune the enantio- and diastereoselective 1,3-dipolar cycloaddition, and providing a pair of

  合成了一对新的具有多个手性中心的P-立体异构体，并将其用于亚铜与亚铜的亚铜酸酯的铜（I）催化对映选择性[3 + 2]环加成反应中。以优异的产率和对映选择性获得了各种高度官能化的吡咯烷。这是一对P-立体异构体作为假对映体的第一个例子，可调节对映体和非对映体选择性的1,3-偶极环加成，并分别提供一对对映体纯的吡咯烷。
• Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines
  作者：Mengna Zhi、Zhenjie Gan、Rong Ma、Hao Cui、Er-Qing Li、Zheng Duan、François Mathey

  DOI：10.1021/acs.orglett.9b00926

  日期：2019.5.3

  A Ag/P-stereogenic phosphine-complex-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with electron-deficient olefins is reported. In this reaction, highly functionalized pyrrolines with a spiro-quaternary stereogenic center were obtained in good yields (up to 99%) with excellent levels of diastereo- (up to >20:1 dr) and enantioselectivities (up to >99% ee). The chirality of adducts was controlled

  报道了Ag / P-立体异构的膦复合物催化的偶氮甲亚胺的1,3-偶极环加成与缺电子的烯烃。在该反应中，获得了具有螺四元立体构型中心的高度官能化的吡咯啉，收率好（高达99％），非对映体（高达> 20：1 dr）和对映体选择性（高达> 99％ee） 。加合物的手性主要受P-立体生成的膦所控制。
• Primary α-tertiary amine synthesis <i>via</i> α-C–H functionalization
  作者：Dhananjayan Vasu、Angel L. Fuentes de Arriba、Jamie A. Leitch、Antoine de Gombert、Darren J. Dixon

  DOI：10.1039/c8sc05164j

  日期：——

  A quinone-mediated general synthetic platform for the construction of primary α-tertiary amines from abundant primary α-branched amine starting materials is described. This procedure pivots on the efficient in situ generation of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary

  描述了一种醌介导的通用合成平台，用于从丰富的伯 α-支化胺起始材料构建伯 α-叔胺。该过程的重点是有效地原位生成反应性酮亚胺中间体，并随后与碳中心亲核试剂（例如有机镁和有机锂试剂以及 TMSCN）反应，产生四元中心。此外，扩展到反极性光氧化还原催化可以通过亲核α-氨基自由基中间体与亲电子试剂发生反应。这种高效、广泛适用且可扩展的胺对胺合成平台已成功应用于库和 API 合成以及药物分子的功能化。
• Directing Group‐Free Formal Suzuki–Miyaura Coupling of Simple Ketones Enabled by Activation of Unstrained C−C Bonds
  作者：Jiangkun Huang、Xufei Yan、Ying Xia

  DOI：10.1002/anie.202211080

  日期：2022.12.5

  A Rh-catalyzed directing group-free formal Suzuki–Miyaura coupling reaction was established between simple ketones and arylboronates based on activation of unstrained C−C bonds. The key to the success of this reaction is a nucleophilic addition/β-carbon elimination sequence that can activate the unstrained ketone carbonyl C−C bond without the assistance of directing group.

  基于无应变 C-C 键的活化，在简单酮和芳基硼酸酯之间建立了 Rh 催化的无导向基团形式 Suzuki-Miyaura 偶联反应。该反应成功的关键是一个亲核加成/β-碳消除序列，它可以在没有导向基团帮助的情况下激活未应变的酮羰基 C-C 键。
• Facile Synthesis of 5,10-Diaryl-5,10-dihydrophenazines and Application to EL Devices
  作者：Toshihiro Okamoto、Eriko Terada、Masatoshi Kozaki、Manabu Uchida、Shingo Kikukawa、Keiji Okada

  DOI：10.1021/ol0274458

  日期：2003.2.1

  An efficient method for the synthesis of 5,10-diaryldihydrophenazine was developed using a recently developed Pd(0)-mediated cross-coupling reaction. The products 1k and 3c showed excellent properties as hole injection materials in electroluminescent (EL) devices.