(4-(but-3-en-1-yloxy)phenyl)methanamine | 865539-68-0

• 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-(but-3-en-1-yloxy)phenyl)methanamine
• 英文别名: p-(but-3-enyloxy)benzylamine；p-butenoxybenzylamine；(4-But-3-enoxyphenyl)methanamine
• CAS: 865539-68-0
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: NQZVZJPMBMPTKG-UHFFFAOYSA-N

物化性质

• 沸点：
  288.8±28.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-(but-3-en-1-yloxy)phenyl)methanamine 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 tert-butyl (4-(but-3-en-1-yloxy)benzyl)(4-((6-hydroxyhexyl)oxy)benzyl)carbamate
  参考文献：
  名称：

  多价导向的魔环[2]（3）链烯的烯烃复分解

  摘要：

  仿佛是魔术：在三二烷基铵链离子与三萜衍生的同位三价主体之间形成新型的多价定向络合物的基础上，通过可逆的烯烃复分解反应获得了有趣的魔术环[2]（3）环烷（参见方案）。

  DOI：

  10.1002/chem.201002111
• 作为产物：
  描述：

  苯甲腈,4-(3-丁烯氧基)- 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (4-(but-3-en-1-yloxy)phenyl)methanamine
  参考文献：
  名称：

  Synthesis and structure of a bowl-like molecule by threefold metathesis reactions

  摘要：

  A bowl-like molecule was designed and efficiently synthesized by threefold metathesis reactions, and its structure was determined by NMR, MALDI-TOF MS spectrum, and X-ray crystallographic analysis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.031

文献信息

• Rotaxanes of a macrocyclic ferrocenophane with dialkylammonium axle components
  作者：Yuji Suzaki、Eriko Chihara、Atsuko Takagi、Kohtaro Osakada

  DOI：10.1039/b907417a

  日期：——

  Octaoxa[22]ferrocenophane, 1, was synthesized and employed as the macrocyclic component of [2]rotaxanes. [2]Pseudorotaxanes composed of macrocyclic molecule 1 and dialkylammonium derivatives with a terminal vinyl group undergo end-capping via cross-metathesis of the terminal group with bulky acrylates. The [2]rotaxanes of 1 with axle components having bulky terminal groups, such as 3,5-dimethylphenyl, 9-anthryl, and ferrocenyl groups, maintain an interlocked structure in CDCl3 solution, but they are gradually converted into a mixture of the individual components via dethreading of the end groups in polar solvents such as CD3CN and dmso-d6. The reaction rate varies depending on the end group and solvent. The cationic rotaxane with an anthryl end group of the axle component, [(1)AnCH2NH2CH2C6H4-4-OCH2CH2CHCHCOOC6H4-4-C(C6H4-4-tBu)3}](BArF) (An = 9-anthryl, BArF = BC6H3-3,5-(CF3)2}4) shows weak emission upon excitation of the anthryl group (12b, λem = 419 nm, quantum yield, ϕ = 0.012). The quantum yield is lower than that of the neutral rotaxane 13b (ϕ = 0.030) formed by N-acetylation of 12b and a physical mixture of the corresponding free axle molecule, AnCH2N(Ac)CH2C6H4-4-OCH2CH2CHCHCOOC6H4-4-C(C6H4-4-tBu)3 (8), and 1 (ϕ = 0.34). The efficiency of the quenching caused by the ferrocenylene group caused by energy transfer is affected significantly by the relative positions of the anthryl and ferrocenylene groups in the rotaxane. The rotaxane with axles having a secondary ammonium moiety has a redox potential E1/2 = −0.03–0.02 V (vs. Ag+/Ag), which is lower those of than compound 1 (E1/2 = −0.10 V) and the neutral [2]rotaxanes with the N-acetylated axle components (E1/2 = −0.11 and −0.22 V).

  八氧化[22]铁松烯，为1，已被合成并用作[2]旋转链的宏环成分。由宏环分子1和具有端基乙烯基的二烷基铵衍生物组成的[2]伪旋转链通过与体积较大的丙烯酸酯的端基交叉转位反应进行封端。1与具有体积较大端基的轴心成分（如3,5-二甲基苯基、9-蒽基和铁松烯基团）形成的[2]旋转链在CDCl3溶液中保持互锁结构，但在极性溶剂（如CD3CN和dmso-d6）中，它们逐渐通过端基的解缠转化为各个成分的混合物。反应速率因端基和溶剂的不同而有所变化。具有蒽基端基的阳离子旋转链[(1)AnCH2NH2CH2C6H4-4-OCH2CH2CHCHCOOC6H4-4-C(C6H4-4-tBu)3}](BArF)（An = 9-蒽基，BArF = BC6H3-3,5-(CF3)2}4）在激发蒽基时显示出微弱的发射（12b，λem = 419 nm，量子产率，ϕ = 0.012）。其量子产率低于通过N-乙酰化12b形成的中性旋转链13b（ϕ = 0.030），以及相应的游离轴心分子AnCH2N(Ac)CH2C6H4-4-OCH2CH2CHCHCOOC6H4-4-C(C6H4-4-tBu)3（8）和1的物理混合物（ϕ = 0.34）。由能量转移引起的铁松烯基团造成的猝灭效率在旋转链中蒽基和铁松烯基团的相对位置上受到显著影响。具有二级铵基团的旋转链的氧化还原电位E1/2 = −0.03–0.02 V（相对于Ag+/Ag），低于化合物1的电位（E1/2 = −0.10 V）以及具有N-乙酰化轴心成分的中性[2]旋转链的电位（E1/2 = −0.11和−0.22 V）。
• Ferrocene-containing [2]- and [3]rotaxanes. Preparation via an end-capping cross-metathesis reaction and electrochemical properties
  作者：Yuji Suzaki、Kohtaro Osakada

  DOI：10.1039/b702785k

  日期：——

  Cross-metathesis reactions of terminal olefins with acrylic esters catalyzed by a Ru–carbene complex ((H2IMes)(PCy3)Cl2RuCHPh, H2IMes = N,N-bis(mesityl)-4,5-dihydroimidazol-2-ylidene) were applied to the end-capping of [2]pseudorotaxanes composed of dibenzo[24]crown-8 (DB24C8) and ferrocenylmethylammonium derivatives as the macrocyclic and axle components. A [3]rotaxane consisting of two DB24C8s and an axle molecule having ferrocenyl groups at both ends was obtained from the cross-metathesis reaction of two [2]pseudorotaxanes with Fe(C5H4CH2OCOCHCH2)2. Cyclic voltammograms of the ferrocene-containing rotaxanes show reversible redox reactions whose potentials vary depending on the presence or absence of cationic dialkylammonium groups in the vicinity of the ferrocene units.

  在 Ru-羰基复合物（(H2IMes)(PCy3)Cl2RuCHPh，H2IMes = N,N-双（甲苯甲基）-4、5-二氢咪唑-2-亚基），用于由二苯并[24]冠-8 (DB24C8) 和二茂铁甲基铵衍生物作为大环和轴组分组成的[2]伪罗他烷的端封。通过两个[2]假二十八烷与 Fe(C5H4CH2OCOCHCH2)2 的交叉嵌合反应，得到了由两个 DB24C8 和一个两端带有二茂铁基团的轴分子组成的[3]二十八烷。含二茂铁的轮烷的循环伏安图显示出可逆的氧化还原反应，其电位随二茂铁单元附近阳离子二烷基铵基团的存在与否而变化。
• A Highly Efficient Approach to [4]Pseudocatenanes by Threefold Metathesis Reactions of a Triptycene-Based Tris[2]pseudorotaxane
  作者：Xiao-Zhang Zhu、Chuan-Feng Chen

  DOI：10.1021/ja0546020

  日期：2005.9.28

  A triptycene-based homotritopic host was designed and synthesized. Assembly of the host with a bisbenzylammonium salt containing terminal double bonds resulted in a tris[2]pseudorotaxane, which further performed the threefold metathesis reaction and then hydrogenation to give a [4]pseudocatenane in high yield. The [4]pseudocatenane exhibited a novel topological structure with high symmetry, which was confirmed by the spectral data and X-ray analysis.
• Stepwise Motion in a Multivalent [2](3)Catenane
  作者：Zheng Meng、Ying Han、Li-Na Wang、Jun-Feng Xiang、Sheng-Gui He、Chuan-Feng Chen

  DOI：10.1021/jacs.5b05758

  日期：2015.8.5

  The motions of biomolecular machines are usually multistep processes, and are involved in a series of conformational changes. In this paper, a novel triply interlocked [2] (3)catenane composed of a tris(crown ether) host eTC and a circular ditopic guest with three dibenzyl ammonium (DBA) sites and three N-methyltriazolium (MTA) sites was reported. Due to the multivalency nature of the catenane, the acid base triggered motion was performed by a stepwise manner. The coconformations of the four related stable states have been directly identified and quantified which confirmed the multistep process. In order to quantify the dynamics with environmental acidity changes, the values of the three levels of dissociation constant pK(a) have been determined. The special interlocked topology of the [2](3)catenane also endows the motion of each crown ether ring in the host with unexpected selectivity for the MTA sites. This study provides clues to comprehend the underlying motion mechanism of intricate biological molecular machines, and further design artificial molecular machine with excellent mechanochemistry properties.
• Synthesis and structure of a bowl-like molecule by threefold metathesis reactions
  作者：Jing Cao、Zhi-Ping Song、Xiao-Zhang Zhu、Chuan-Feng Chen

  DOI：10.1016/j.tetlet.2010.04.031

  日期：2010.6

  A bowl-like molecule was designed and efficiently synthesized by threefold metathesis reactions, and its structure was determined by NMR, MALDI-TOF MS spectrum, and X-ray crystallographic analysis. (C) 2010 Elsevier Ltd. All rights reserved.