1,3,5-三丁基苯 | 841-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3,5-三丁基苯
• 英文名称: 1,3,5-tributylbenzene
• 英文别名: 1,3,5-tri-n-butylbenzene；1,3,5-Tributyl-benzol
• CAS: 841-07-6
• 化学式: C₁₈H₃₀
• 分子量: 246.436
• InChiKey: AVYPEYYPGYMFDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  1,3,5-三丁基苯 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氯化碳 为溶剂， 以8%的产率得到1,3,5-tri-N-butyl-2,4,6-triiodobenzene
  参考文献：
  名称：

  1,3,5-Trialkyl-2,4,6-triiodobenzenes:  Novel X-ray Contrast Agents for Gastrointestinal Imaging

  摘要：

  Examination of the gastrointestinal (GI) tract has been performed for decades using barium sulfate. Although this agent has many recognized limitations including extreme radiopacity, poor intrinsic affinity for the GI mucosa, and very high density, no alternative contrast agents have emerged which produce comparable or better contrast visualization. In fact, the various techniques of the GI radiologic examination (i.e., single contrast, double contrast, biphasic) were developed to compensate for its limitations. Each of these techniques requires complex patient manipulation to achieve adequate mucosal coating or compression to overcome the marked radiopacity of barium sulfate in order to obtain a diagnostically useful examination. A Series of novel radiopaque oils, the 1,3,5-trialkyl-2,4,6-triiodobenzenes, was designed to improve the efficacy, stability, and safety of barium formulations. These substances were prepared in two steps from 1,3,5-trichlorobenzene. Compound 17 (1,3,5-tri-n-hexyl-2,4,6-triiodobenzene) formulated as an oil-in-water emulsion, was found to be well-tolerated in rodents (mice, hamsters, rats) following acute oral and/or intraperitoneal administrations at 4 times the anticipated human clinical dose. No metabolism of 17 was detected in rat, hamster, dog, monkey, or human hepatic microsomes, suggesting the lack of oral toxicity was a consequence of poor absorption.

  DOI：

  10.1021/jm990407i
• 作为产物：
  描述：

  1-己炔 在 bis(acetylacetonate)nickel(II) 、 二甲基苯基磷 作用下， 反应 6.0h， 生成 1,3,5-三丁基苯
  参考文献：
  名称：

  Ni和Pd催化的双炔化和末端炔烃的双硒代化中的显着配体效应：解决了立体选择性二烷基二卤化碳加成到C三化学键C键的问题。

  摘要：

  我们已经开发了两个基于Ni和Pd配合物的新催化系统，以解决二炔二卤化物（Alk2E2; E = S，Se）加成炔烃这一具有挑战性的问题。对两种催化剂体系Ni / PMe2Ph和Pd / PCy2Ph的比较研究表明，Ni催化剂在高催化活性方面优于Pd体系，具有更广泛的适用范围。开发了一种新颖的合成方法，用于从末端炔烃中以优异的立体选择性和高收率制备（Z）-双（烷硫基）烯烃和（Z）-双（烷基硒基）烯烃。

  DOI：

  10.1002/chem.200701278

文献信息

• Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing
  作者：Shin-ichi Sasaki、Daniel Citterio、Satoru Ozawa、Koji Suzuki

  DOI：10.1039/b105913k

  日期：2001.11.29

  Expecting a preorganization effect, tripodal anion host molecules were designed and synthesized. It was demonstrated that two kinds of new thiourea derivatives having a six-fold substituted benzene ring as a preorganized spacer were effective for recognition of the tetrahedral dihydrogen phosphate anion. A tripodal fluororeceptor 1 having a pyrene moiety adjacent to the thiourea binding site showed long-wavelength emission upon addition of guest anions in acetonitrile. On the other hand, a tripodal thiourea receptor 2 connected to anthracene groups via methylene units showed a decrease in fluorescence intensity upon addition of anions. In both cases, the degree of the change in emission intensity was in the order of H2PO4− > CH3COO− > Cl− ≫ ClO4−, which is clearly different from that of reference compounds having only one binding site. Association constants (Ka) of these tripodal fluororeceptors also confirmed the dihydrogen phosphate selectivity over the more basic acetate anion in this homogeneous solution system. The characteristics of the fluororeceptors using the preorganization effect were shown to be promising for the development of chemical ion sensors with a specific anion selectivity.

  预期存在前组织效应，设计并合成了三脚架型阴离子主体分子。研究表明，两种新型硫脲衍生物，其六取代苯环作为前组织间隔基，能有效识别四面体磷酸二氢根离子。具有吡啶并环部分与硫脲结合位点相邻的三脚架型氟光受体1在加入客体阴离子后，在乙腈中表现出长波长发射。另一方面，通过亚甲基单元与蒽基团相连的三脚架型硫脲受体2在加入阴离子后荧光强度降低。在这两种情况下，发射强度的变化程度依次为H2PO4^- > CH3COO^- > Cl^- ≫ ClO4^-，这与仅有一个结合位点的参考化合物明显不同。这些三脚架型氟光受体的结合常数（Ka）也证实了在该均相溶液系统中对磷酸二氢根离子相对于更基础的醋酸根离子的选择性。利用前组织效应的氟光受体特征显示出有望开发具有特定阴离子选择性的化学离子传感器。
• Stereodivergent Formation of Alkenylsilanes:syn oranti Hydrosilylation of Alkynes Catalyzed by a Cyclopentadienylcobalt(I) Chelate Bearing a Pendant Phosphane Tether
  作者：Li Yong、Karin Kirleis、Holger Butenschön

  DOI：10.1002/adsc.200606028

  日期：2006.5

  alkynes is catalyzed by the di-tert-butylphosphanylethylcyclopentadienylcobalt chelate 1. While the reaction of internal alkynes exclusively affords syn hydrosilylation products with triethylsilane, the reaction with triethoxysilane shows predominant anti stereoselectivity. Reactions of terminal alkynes are less selective with triethylsilane and result in cyclotrimerization when triethoxysilane is used

  炔烃的氢化硅烷化反应是由二叔丁基膦烷基乙基环戊二烯基钴螯合物1催化的。虽然内部炔烃的反应仅提供与三乙基硅烷的合成氢化硅烷化产物，但与三乙氧基硅烷的反应显示出主要的抗立体选择性。末端炔烃与三乙基硅烷的反应选择性较低，使用三乙氧基硅烷时会导致环三聚。
• General and highly efficient fluorinated-N-heterocyclic carbene–based catalysts for the palladium-catalyzed Suzuki–Miyaura reaction
  作者：Taoping Liu、Xiaoming Zhao、Qilong Shen、Long Lu

  DOI：10.1016/j.tet.2012.05.068

  日期：2012.8

  acid with aryl halides and heteroaryl halides, but also efficient for coupling of other heteroaryl halides and heteroaryl boronic acids. Finally, the catalyst is highly effective for Suzuki–Miyaura reaction of aryl bromides and chlorides with 0.01–0.1 mol % loading if the temperature was raised at refluxed THF/H2O.

  据报道，一种通用且高效的三氟甲基化-N-杂环卡宾（NHC）基催化剂可用于钯催化的Suzuki-Miyaura反应。在催化剂的存在下，未活化的芳基氯和三氟甲磺酸与芳基硼酸的反应在室温下发生，收率好至极好（63-98％）。此外，由Pd（OAc）2 /咪唑鎓盐6a的组合产生的催化剂不仅对于杂芳基硼酸与芳基卤化物和杂芳基卤化物的偶联有效，而且对其他杂芳基卤化物和杂芳基硼酸的偶联有效。最后，如果温度在回流的THF / H 2 O上升高，则该催化剂对于0.01-0.1 mol％负载量的芳基溴化物和氯化物的Suzuki-Miyaura反应非常有效。
• A Highly Practical <i>Instant</i> Catalyst for Cyclotrimerization of Alkynes to Substituted Benzenes
  作者：Naoko Saino、Fumihiro Amemiya、Emi Tanabe、Kouki Kase、Sentaro Okamoto

  DOI：10.1021/ol0602295

  日期：2006.3.1

  see text] A 2-(2,6-diisopropylphenyl)iminomethylpyridine (1a)/CoCl(2).6H(2)O/Zn reagent has been developed as an effective instant catalyst for the intra- and intermolecular cyclotrimerization of alkynes to substituted benzenes, making the method extremely practical since the reagent, 1a/CoCl(2).6H(2)O/Zn, is inexpensive and easy to handle and the reaction is less sensitive to moisture and is reasonably

  [反应：见正文] 2-（2,6-二异丙基苯基）亚氨基甲基吡啶（1a）/ CoCl（2）.6H（2）O / Zn试剂已被开发为一种有效的即时催化剂，用于分子内和分子间环三聚炔烃与取代的苯反应，使该方法极为实用，因为1a / CoCl（2）.6H（2）O / Zn试剂价格低廉且易于处理，并且反应对水分的敏感性较低，并且反应一般。
• Efficient Intermolecular [2 + 2 + 2] Alkyne Cyclotrimerization in Aqueous Medium Using a Ruthenium(IV) Precatalyst
  作者：Victorio Cadierno、Sergio E. García-Garrido、José Gimeno

  DOI：10.1021/ja066552k

  日期：2006.11.1

  bis(allyl)-ruthenium(IV) complex [Ru(eta3:eta3-C10H16)(mu-Cl)Cl}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) was found to catalyze efficiently the [2 + 2 + 2] cyclization of terminal and internal alkynes in aqueous medium.

  二聚体双（烯丙基）-钌（IV）络合物 [Ru(eta3:eta3-C10H16)(mu-Cl)Cl}2] (C10H16 = 2,7-二甲基辛基-2,6-二烯-1,8- diyl) 被发现有效地催化水性介质中末端和内部炔烃的 [2 + 2 + 2] 环化。

表征谱图