diphenylborinic acid 3-benzylcarbamoyl-propyl ester | 1144099-52-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diphenylborinic acid 3-benzylcarbamoyl-propyl ester
• 英文别名: diphenylborinic acid 3-benzylcarbamoylpropyl ester；N-benzyl-4-diphenylboranyloxybutanamide
• CAS: 1144099-52-4
• 化学式: C₂₃H₂₄BNO₂
• 分子量: 357.26
• InChiKey: MNYGBZAFQXWSRU-UHFFFAOYSA-N

物化性质

• 沸点：
  549.7±50.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苄基-4-羟基丁酰胺 、 二苯基硼酸酐 以 甲苯 为溶剂， 以88%的产率得到diphenylborinic acid 3-benzylcarbamoyl-propyl ester
  参考文献：
  名称：

  Seven membered ring chelates derived from γ-hydroxyamides and triphenyltin or diphenylboron

  摘要：

  N-Benzyl-4-hydroxy-butyramide (1), 4-hydroxy-N-[(R)-1-phenyl-ethyl]-butyramide (2), and (R)-4hydroxy-2-methyl-N-[(R)-1-phenyl-ethyl]-butyramide (3a) were used to prepare new diphenylboron and triphenyltinoxy compounds: diphenylborinic acid 3-benzylcarbamoyl-propyl ester (4), diphenylborinic acid 3-[(R)-1-phenyl-ethylcarbamoyl]-propyl ester (5) and diphenylborinic acid (R)-3-[(R)-1-phenyl-ethylcarbamoyl]-butyl ester (6), N-benzyl-4-triphenyltinoxy-butyramide (7), 4-triphenyltinoxy-N-[(R)-1-phenyl-ethyl]-butyramide (8), and (R)-4-triphenyltinoxy-2-methyl-N-[(R)-1-phenyl-ethyl]-butyramide (9). The X-ray diffraction analysis of a crystalline structure of the new gamma-hydroxyamide 3a is reported, as well as that of the first example of a crystalline structure where a diphenylborinic ester forms a seven membered chelate, by a carbonyl coordination to boron (4). Structural studies of tin and boron esters were performed by NMR. The C=O internal coordination to tin atoms, affording seven membered rings, was observed by Sn-119 NMR experiments at low temperature. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.10.039

文献信息

• Seven membered ring chelates derived from γ-hydroxyamides and triphenyltin or diphenylboron
  作者：Raúl Salas-Coronado、Raúl Colorado-Peralta、Sonia A. Sánchez-Ruiz、Rosalinda Contreras、Angelina Flores-Parra

  DOI：10.1016/j.jorganchem.2008.10.039

  日期：2009.3

  N-Benzyl-4-hydroxy-butyramide (1), 4-hydroxy-N-[(R)-1-phenyl-ethyl]-butyramide (2), and (R)-4hydroxy-2-methyl-N-[(R)-1-phenyl-ethyl]-butyramide (3a) were used to prepare new diphenylboron and triphenyltinoxy compounds: diphenylborinic acid 3-benzylcarbamoyl-propyl ester (4), diphenylborinic acid 3-[(R)-1-phenyl-ethylcarbamoyl]-propyl ester (5) and diphenylborinic acid (R)-3-[(R)-1-phenyl-ethylcarbamoyl]-butyl ester (6), N-benzyl-4-triphenyltinoxy-butyramide (7), 4-triphenyltinoxy-N-[(R)-1-phenyl-ethyl]-butyramide (8), and (R)-4-triphenyltinoxy-2-methyl-N-[(R)-1-phenyl-ethyl]-butyramide (9). The X-ray diffraction analysis of a crystalline structure of the new gamma-hydroxyamide 3a is reported, as well as that of the first example of a crystalline structure where a diphenylborinic ester forms a seven membered chelate, by a carbonyl coordination to boron (4). Structural studies of tin and boron esters were performed by NMR. The C=O internal coordination to tin atoms, affording seven membered rings, was observed by Sn-119 NMR experiments at low temperature. (C) 2008 Elsevier B.V. All rights reserved.