N-(5-benzyloxy-2-pentynyl)phthalimide | 219756-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(5-benzyloxy-2-pentynyl)phthalimide
• 英文别名: 2-(5-Phenylmethoxypent-2-ynyl)isoindole-1,3-dione
• CAS: 219756-76-0
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: LTCDVISGRJRAKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-benzyloxy-2-pentynyl)phthalimide 在 dimethyl sulfide 、 Pd/C 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and characterization of a protected amino alcohol containing ortho-carborane

  摘要：

  The reaction between the alkyne, N-(5-Benzyloxy-2-pentynyl)phthalimide and decaborane (14) in the presence of dimethyl sulfide resulted in the isolation of 1-C6H4(CO)(2)NCH2-2-C6H5CH2OCH2CH2-1, 2-C2B10H10 (5), 1-methylphthalimido-2-ethylbenzyl ether-o-carborane, in moderate yield. Compound 5 was characterized by single crystal X-ray diffraction study. Compound 5 crystallizes in the PT space group, a = 10.5328 (5) Angstrom, b = 11.9209 (6) Angstrom, c = 10.3451 (3) Angstrom, alpha = 110.492 (3)degrees, beta = 102.868 (3)degrees, gamma = 87.279 (2)degrees, Z = 2, D-calc = 1.226 g/cm(3), R = 0.0491 for 3521 reflections with F>4.0 sigma. Deprotection of the ether linkage of 5 results in the formation of 1-C6H4(CO)(2)NCH2-2-HOCH2CH2-1, 2-C2B10H10 (6), 1-methylphthalimido-2-ethylalcohol-o-carborane. The transformation is accomplished by hydrogenation of (5) over a Pd/C catalyst and resulted in the efficient conversion of (5) into (6) (83% yield). Experimental details and analytical data leading to the identification of the reported compounds is provided. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(98)00121-1