(N-B)phenyl[iminodiacetate-O,N]borane | 109674-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (N-B)phenyl[iminodiacetate-O,N]borane
• 英文别名: (N->B)-phenyl[iminodiacetate-O,O',N]borane；phenyl(iminodiacetate-O,O',N)borane；1-Phenyl-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octane-3,7-dione
• CAS: 109674-44-4
• 化学式: C₁₀H₁₀BNO₄
• 分子量: 219.005
• InChiKey: HTSMDCXDYUINGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.17
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (N-B)phenyl[iminodiacetate-O,N]borane 、 2-碘乙酰胺 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以43%的产率得到(N->B)phenyl[N-carbamoylmethyl-aminodiacetate-O,O',N]borane
  参考文献：
  名称：

  Syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes

  摘要：

  The syntheses of (N-->B)phenyl[N-alkylaminodiacetate-O,O',N]boranes (2 to 6) and their corresponding N-alkylaminodiacetic acids (7 to 10) are reported. All compounds (except 6) were characterized by H-1, B-11 (for boron heterocycles), C-13 NMR, infrared spectroscopy and mass spectrometry. The H-1 NMR spectrum of compound 3 shows that it is a chiral molecule, its structure was determined by homonuclear decoupling experiments, H-1 NMR and HETCOR. The study of the intramolecular N-->B coordination by dynamic NMR afforded a Delta G double dagger value of 98.4 kJ mol(-1) for compound 3. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0277-5387(96)00109-x
• 作为产物：
  描述：

  亚氨基二乙酸 、 苯硼酸 以 二甲基亚砜 、 苯 为溶剂， 以79%的产率得到(N-B)phenyl[iminodiacetate-O,N]borane
  参考文献：
  名称：

  源自亚氨基二乙酸的新型双环有机基硼酸酯

  摘要：

  苯基硼酸或dinethylthexyboronic酯与iminodiacetic-或反应ñ -methyliminodiacetic酸导致高产率的空气稳定的双环酯（NB）苯基[iminodiacete- ø，Ñ ]硼烷（1），（NB）苯基[ Ñ - methyliminodiacetate- ø，ñ ]硼烷（2），（NB）thexy [亚氨基二乙酸[ ø，ñ ]硼烷（3）和（NB）叔己基[ ñ -methyliminodiacetate- ø，ñ ]硼烷（4）。这些由1 H，11 B和13表示13 C NMR光谱显示具有强分子内NB配位的刚性双环结构。

  DOI：

  10.1016/0022-328x(86)80169-3

文献信息

• New strategy to the synthesis of (N→B) phenyl[N-alkyliminodiacetate-O,O′,N]boranes: The crystal structure of (N→B) phenyl[N-benzyliminodiacetate-O,O′,N]borane, (N→B)phenyl[N-(4-methyl)benzyliminodiacetate-O,O′,N]borane and (N→B) phenyl[N-phenacyliminodiacetate-O,O′,N]borane
  作者：Teresa Mancilla Percino、Roxana Magaly Flores Ancona、Marisol López Martínez

  DOI：10.1016/j.poly.2009.05.043

  日期：2009.9

  A new, mild and friendly method for the synthesis of (N -> B) pheny[N-alkyliminodiacetate-O,O',N]boranes 2-7 is reported. All compounds were identified by H-1, B-11, C-13 NMR and their high resolution mass spectra (HRMS) are reported. The structure of the compounds 2, 4 and 5 were established by single crystal X-ray. Compounds 2 and 4 crystallized with two independent molecules 2A, 2B and 4A, 4B. respectively in the asymmetric unit. These molecular structures established the bicyclic structure showing a N -> B bond length of 1.666 (2) angstrom for 2A, 1.675 (2) angstrom for 2B, 1.675 (3) angstrom for 4A, 1.663 (3) angstrom for 4B and 1.679 (2) angstrom for 5, as well as different torsion angles of the junction, 28.70 (2)degrees (C11-B1-N6-C17) for 2A, 21.50 (2)degrees (C11a-B1a-N6a-C17a) for 2B, 25.76 (0.26)degrees (C11-B1-N6-C17) for 4A, 21.96 (0.28)degrees (C11a-B1a-N6a-C17a) for 4B and -29.22 (0.20)degrees (C5-N1-B1-C13) for 5. (C) 2009 Elsevier Ltd. All rights reserved.
• Syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes
  作者：Teresa Mancilla、Lourdes Carrillo、Ma.de la Paz Reducindo

  DOI：10.1016/0277-5387(96)00109-x

  日期：1996.8

  The syntheses of (N-->B)phenyl[N-alkylaminodiacetate-O,O',N]boranes (2 to 6) and their corresponding N-alkylaminodiacetic acids (7 to 10) are reported. All compounds (except 6) were characterized by H-1, B-11 (for boron heterocycles), C-13 NMR, infrared spectroscopy and mass spectrometry. The H-1 NMR spectrum of compound 3 shows that it is a chiral molecule, its structure was determined by homonuclear decoupling experiments, H-1 NMR and HETCOR. The study of the intramolecular N-->B coordination by dynamic NMR afforded a Delta G double dagger value of 98.4 kJ mol(-1) for compound 3. Copyright (C) 1996 Elsevier Science Ltd
• New bicyclic organylboronic esters derived from iminodiacetic acids
  作者：Teresa Mancilla、Rosalinda Contreras、Bernd Wrackmeyer

  DOI：10.1016/0022-328x(86)80169-3

  日期：1986.6

  The reactions of phenylboronic acid or dinethylthexyboronic ester with iminodiacetic- or N-methyliminodiacetic acids lead to high yield to the air-stable bicyclic esters (N-B)phenyl[iminodiacete-O,N]borane (1), (N-B)phenyl[N-methyliminodiacetate-O,N]borane (2), (N-B)thexy[iminodiacetate[O,N]borane (3) and (N-B)thexyl[N-methyliminodiacetate-O,N]borane (4). These are shown by 1H, 11B and 13C NMR spectroscopy

  苯基硼酸或dinethylthexyboronic酯与iminodiacetic-或反应ñ -methyliminodiacetic酸导致高产率的空气稳定的双环酯（NB）苯基[iminodiacete- ø，Ñ ]硼烷（1），（NB）苯基[ Ñ - methyliminodiacetate- ø，ñ ]硼烷（2），（NB）thexy [亚氨基二乙酸[ ø，ñ ]硼烷（3）和（NB）叔己基[ ñ -methyliminodiacetate- ø，ñ ]硼烷（4）。这些由1 H，11 B和13表示13 C NMR光谱显示具有强分子内NB配位的刚性双环结构。