Dimethylammonium borodicatecholate | 53992-90-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Dimethylammonium borodicatecholate
• 英文别名: dimethylazanium;8,8'-spirobi[7,9-dioxa-8-boranuidabicyclo[4.3.0]nona-1,3,5-triene]
• CAS: 53992-90-8
• 化学式: C₂H₇N*C₁₂H₈BO₄*H
• 分子量: 273.096
• InChiKey: UWZZEUCRWVYWLP-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethylammonium borodicatecholate 、 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  螺硼酸键交换实现分子和聚合物结构中的动态共价自排序

  摘要：

  螺硼酸盐复分解已通过小分子模型反应得到证实，该反应涉及螺硼酸盐连接的明确的聚合物和分子结构。由动态共价自排序驱动的螺硼酸键交换通过形成分子笼导致大环和一维螺旋共价聚合物之间的混乱，所有结构均通过单晶 X 射线衍射明确阐明。

  DOI：

  10.1002/anie.202304279
• 作为产物：
  描述：

  三(二甲基氨基)硼烷 、 邻苯二酚 以 乙醚 为溶剂， 以91%的产率得到Dimethylammonium borodicatecholate
  参考文献：
  名称：

  Bis-Catecholate, Bis-Dithiocatecholate, and Tetraalkoxy Diborane(4) Compounds:  Aspects of Synthesis and Electronic Structure

  摘要：

  The synthesis and characterization of a series of bis-catecholate diborane(4) compounds, B-2(1,2-O2C6H4)(2) (3), B-2(1,2-O-2-3-MeC6H3)(2) (6), B-2(1,2-O-2-4-MeC6H3)(2) (7), B-2(1,2-O-2-4-(BuC6H3)-C-t)(2) (8), B-2(1,2-O-2-3,5-(Bu2C6H2)-C-t)(2) (9), B-2(1,2-O-2-3-MeOC6H3)(2) (10), bis-ditkiocatecholate diborane(3) compounds, B-2(1,2-S2C6H4)(2) (13), B-2(1,2-S-2-4-MeC6H3)(2) (14), and tetraalkoxy diborane(4) compounds, B-2(OCH2CMe2CH2O)(2) (11) and B-2(OCMe2CMe2O)(2) (12) from B-2(NMe2)(4) (1) is described, as are the bis(NHMe2) adducts or 3 and 9, namely [B-2(1,1-O2C6H4)(2)-(NHMe2)(2)] (1) and [B-2(1,2-O-2-3,5-(Bu2C6H2)-C-t)(2)(NHMe2)(2)] (5). The latter two compounds are intermediates in thr formation of 3 and 9 from 1. Compound 1 is synthesized by reductive coupling of BCl(NMe2)(2), which in turn is prepared from reaction of BCl3 with B(NMe2)(3) in a 1:2 stoichiometry. We have also tharacterized [B2Cl4- (NHMe2)(2)] (15) formed from addition of HCl to 1 prior to complete reaction with diols, and the salt, [NH2Me2][B(1,2-O2C6H3)(2)] (16) which arises from addition of catechol to B(NMe2)(3). Thus, any B(NMe2)(3) impurity present after the preparation of 1 needs to be removed by distillation prior to reaction with alcohols. The dimer, [BCl2-(mu-NMe2)](2) (17) has also been characterized. This is formed from reaction of BCl3 with B(NMe2)(3) if a 2:1 rather than 1:2 stoichiometry is used. Photoelectron spectra of 1, 3, 8, 11, and 12 are reported along with those of the corresponding diols, catechol, 4-Bu-t-catechol, 2,2-dimethyl-1,3-propanediol. and pinacol. The ionization energies of the B-2(OR)(4) compounds follow the series 8 < 3 < 12 < 11. Replacement of O for N in the B2N4 framework increases the IE by ca. 1.65 eV, whereas the presence of an aromatic ring rather than an aliphatic chain decreases the IE by ca. 1.50 eV. The presence of electron donating Bu-t-gr oups also decreases the IE.

  DOI：

  10.1021/ic980425a

文献信息

• Selective C−N Borylation of Alkyl Amines Promoted by Lewis Base
  作者：Jiefeng Hu、Guoqiang Wang、Shuhua Li、Zhuangzhi Shi

  DOI：10.1002/anie.201809608

  日期：2018.11.12

  synthesize various alkyl potassium trifluoroborate salts is introduced. The key to this high reactivity is the utilization of pyridinium salt activated alkylamines, with a catalytic amount of a bipyridine‐type Lewis base as a promoter. This transformation shows good functional‐group compatibility (e.g., it is unimpeded by the presence of a ketone, indole, internal alkene, or unactivated alkyl chloride) and

  引入了一种有效的方法，以双（邻苯二酚）二硼作为硼源，直接合成各种三氟硼酸烷基钾盐，从而实现烷基胺的无金属脱氨基硼化。如此高的反应活性的关键是利用吡啶盐活化的烷基胺，并以催化量的联吡啶型路易斯碱作为促进剂。这种转变显示出良好的官能团相容性（例如，不受酮，吲哚，内部烯烃或未活化的烷基氯的存在的阻碍），并且可以用作复杂化合物中胺基的硼酸酯化的强大合成工具。力学实验和计算表明了一种机制，其中路易斯碱激活了B 2 cat 2 单元截获由硼还原剂单电子转移（SET）产生的烷基。