N-(4-methoxybenzyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

• 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: N-(4-methoxybenzyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine
• 英文别名: N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-methoxybenzylamine；N-(4-methoxybenzyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline；N-[(4-methoxyphenyl)methyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• 化学式: C₂₀H₂₆BNO₃
• 分子量: 339.242
• InChiKey: SZETYZSFGRDOCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基苯硼酸频哪醇酯 在 H₂O 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 N-(4-methoxybenzyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine
  参考文献：
  名称：

  Synthesis and antifungal properties of benzylamines containing boronate esters

  摘要：

  将3-H₂NC₆H₄Bpin（pin = 1,2-O₂C₂Me₄）加入一系列醛和4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯乙酮，得到相应的苄亚胺，产率在中等到高收率之间。这些亚胺与邻苯二酚硼烷（HBcat，cat = 1,2-O₂C₆H₄）在室温下氢化硼化，经水工作后得到相应的硼胺。对由9-蒽醛和3-H₂NC₆H₄Bpin制备的亚胺1h进行了X射线衍射研究。1h的晶体为三斜晶系，a = 9.6793(4) Å，b = 10.7397(4) Å，c = 11.5353(4) Å，α = 105.1890(10)^o，β = 97.3030(10)^o，γ = 102.1480(10)^o，Z = 2，空间群为P[Formula: see text]；N-[3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯基]-4-甲氧基苄胺2c的晶体为正交晶系，a = 8.6612(4) Å，b = 10.3794(4) Å，c = 20.6033(9) Å，Z = 4，空间群为P2₁2₁2₁。已对胺类化合物进行了抗真菌性能测试，针对曲霉和黄曲霉。关键词：苄胺，硼酸酯，氨基硼，氢化硼，抗真菌。

  DOI：

  10.1139/v01-090

文献信息

• PXPd-catalyzed borylation of aniline derivatives
  作者：Susan Wheaton、S. Humanayun Kabir、Haiwen Zhang、Christopher Vogels、Andreas Decken、Stephen Westcott

  DOI：10.2478/s11532-010-0076-1

  日期：2010.8.1

  Addition of pinacolborane (HBO2C2Me4) to 2-iodoaniline can be catalyzed using a number of palladium complexes, including [(t-Bu)2PCl]2PdCl2 (PXPd), to give the corresponding boronate ester 2-H2NC6H4(BO2C2Me4) in excellent yields. The PXPd system could also be used in the catalyzed borylation of substituted anilines to give the corresponding aminoboronate esters in moderate to high yields.

  摘要：将双醇硼烷（HBO2C2Me4）加到2-碘苯胺中可以使用多种钯配合物催化，包括[(t-Bu)2PCl]2PdCl2（PXPd），可获得相应的硼酸酯2-H2NC6H4(BO2C2Me4)且收率很高。PXPd系统还可用于催化取代苯胺的硼化反应，得到相应的氨硼酸酯，收率在中等到高收率之间。
• Synthesis and antifungal properties of benzylamines containing boronate esters
  作者：Christopher M Vogels、Liliya G Nikolcheva、David W Norman、Heather A Spinney、Andreas Decken、Mark O Baerlocher、Felix J Baerlocher、Stephen A Westcott

  DOI：10.1139/v01-090

  日期：2001.7.1

  Addition of 3-H₂NC₆H₄Bpin (pin = 1,2-O₂C₂Me₄) to a series of aldehydes and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acetophenone afforded the corresponding benzylideneamines in moderate to high yields. Hydroboration of these imines with catecholborane (HBcat, cat = 1,2-O₂C₆H₄) at room temperature gives, upon aqueous workup, the corresponding borylamines. An X-ray diffraction study was carried out on imine 1h derived from 9-anthraldehyde and 3-H₂NC₆H₄Bpin. Crystals of1h were triclinic, a = 9.6793(4) Å, b = 10.7397(4) Å, c = 11.5353(4) Å, α = 105.1890(10)^o, β = 97.3030(10)^o, γ = 102.1480(10)^o, Z = 2 with space group P[Formula: see text] and crystals of N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-methoxybenzylamine 2c were orthorhombic, a = 8.6612(4) Å, b = 10.3794(4) Å, c = 20.6033(9) Å, Z = 4 with space group P2₁2₁2₁. Amines have been tested for their antifungal properties against Aspergillus niger and Aspergillus flavus.Key words: benzylamines, boronate esters, aminoboron, hydroboration, antifungal.

  将3-H₂NC₆H₄Bpin（pin = 1,2-O₂C₂Me₄）加入一系列醛和4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯乙酮，得到相应的苄亚胺，产率在中等到高收率之间。这些亚胺与邻苯二酚硼烷（HBcat，cat = 1,2-O₂C₆H₄）在室温下氢化硼化，经水工作后得到相应的硼胺。对由9-蒽醛和3-H₂NC₆H₄Bpin制备的亚胺1h进行了X射线衍射研究。1h的晶体为三斜晶系，a = 9.6793(4) Å，b = 10.7397(4) Å，c = 11.5353(4) Å，α = 105.1890(10)^o，β = 97.3030(10)^o，γ = 102.1480(10)^o，Z = 2，空间群为P[Formula: see text]；N-[3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯基]-4-甲氧基苄胺2c的晶体为正交晶系，a = 8.6612(4) Å，b = 10.3794(4) Å，c = 20.6033(9) Å，Z = 4，空间群为P2₁2₁2₁。已对胺类化合物进行了抗真菌性能测试，针对曲霉和黄曲霉。关键词：苄胺，硼酸酯，氨基硼，氢化硼，抗真菌。