(甲氧基羰基)三甲基硼胺 | 91993-52-1

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 中文名称: (甲氧基羰基)三甲基硼胺
• 中文别名: 硼内胺盐甲酯；(甲氧羰基)硼烷三甲胺络合物；三甲胺-甲氧羰基硼烷
• 英文名称: trimethylamine-carbomethoxyborane
• 英文别名: trimethylamine-methoxycarbonylborane；Methoxycarbonyl-(trimethylazaniumyl)boranuide；methoxycarbonyl-(trimethylazaniumyl)boranuide
• CAS: 91993-52-1
• 化学式: C₅H₁₄BNO₂
• 分子量: 130.983
• InChiKey: XRWCWUJXGVSVTN-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(lit.)
• 稳定性/保质期：

  避免接触强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• RTECS号：
  ED7685000

反应信息

• 作为反应物：
  描述：

  (甲氧基羰基)三甲基硼胺 以 甲醇 、 乙腈 为溶剂， 生成 trimethylamine-cyano(methoxycarbonyl)borane
  参考文献：
  名称：

  Synthesis and examination of amine-cyanocarboxyboranes, the boron analogues of α-cyanocarboxylic acids: X-ray structural study of the first lactam containing a boron atom in the lactam ring

  摘要：

  The first representatives of chiral boron atom-containing amine-cyanomethoxycarbonyl boranes (A . BH(CN)COOMe) have been synthesized either from the corresponding amine-bromocyanomethoxycarbonylborane complexes with [BU4N]CN or from Me3N.BH(CN)COOMe and an amine in a base-exchange reaction. Acid hydrolyses of methyl esters generated the free acids (A.BH(CN)COOH), which are isoelectronic to the alpha-cyano carboxylic acids. Their pK(a) values and hydrolysis half-lives in acidic medium (that is rate of proton reduction) have been determined. Similarly to the alpha cyano carboxylic acids, the cyano group attached to the boron (in alpha position to the COOH group) increased the acid strength of carboxy boranes with 2.0-2.5 orders of magnitude. Independently from the type of the amine, pK(a) values of the amine-cyanocarboxyhoranes (6.34-5.82) decrease consistently with the increase of pK(b) values of the amines. Hydrolytic decomposition rate of the alkylamine complexes increases with increasing pKb values of the amines while the opposite was found for pyridine base complexes. When considering both types of the amines, hydrolysis half-lives of the complexes range over several orders of magnitude from 0.005 to 400 h. Based on these observations protonation of the amine nitrogen atom appears to be the rate determining step in the hydrolysis process. With loss of methanol, 2-NH2-py.BH(CN)COOMe transformed into a five membered lactam derivative. X-ray diffraction revealed that the pyridine ring is coplanar with the five membered lactam ring. In the crystal two molecules are connected in a head to tail arrangement by strong intermolecular H-bonds between N(2)-H and the carbonyl oxygen (01) with a donor and acceptor distance of 2.867(3) A. Three new cyanomethoxycarbonylborates having the composition of K[BHn(CN)(3-n)COOMe] (n = 1, 2) and K[B(OH)(CN)(2-) COOMe] have also been synthesized and their properties examined. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.06.066

文献信息

• SYNTHESES OF NOVEL SUBSTITUTED-BORANOPHOSPHATE NUCLEOSIDES
  作者：Kamesh Vyakaranam、Geeta Rana、Bernard F. Spielvogel、John A. Maguire、Narayan S. Hosmane

  DOI：10.1081/ncn-120015070

  日期：2002.11

  cyano, carboxy, or carbamoyl) borano] deoxynucleosides (3a-4c) and 5'-[diethylphosphite(cyano or carboxy) borano] deoxynucleosides (6a-7d) were prepared by a variety of synthetic procedures. The syntheses of the pyrophosphates (2a-2c), as precursors for 3a-4c, are also described.

  许多取代的（硼烷）核酸，3'-[亚磷酸二乙酯（氰基，羧基或氨基甲酰基）硼烷]脱氧核苷（3a-4c）和5'-[亚磷酸二乙酯（氰基或羧基）硼烷]脱氧核苷（6a-7d）通过各种合成程序制备。还描述了作为3a-4c的前体的焦磷酸盐（2a-2c）的合成。
• Sood, Anup; Spielvogel, Bernard F., Inorganic Chemistry, 1992, vol. 31, # 12, p. 2654 - 2655
  作者：Sood, Anup、Spielvogel, Bernard F.

  DOI：——

  日期：——