cyclopropanecarboxylic acid N'-(2-naphthalen-2-yl-acetyl)-hydrazide | 865811-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: cyclopropanecarboxylic acid N'-(2-naphthalen-2-yl-acetyl)-hydrazide
• 英文别名: N'-(2-naphthalen-2-ylacetyl)cyclopropanecarbohydrazide
• CAS: 865811-81-0
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: PKUALDYDRCQEMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclopropanecarboxylic acid N'-(2-naphthalen-2-yl-acetyl)-hydrazide 在 四碘甲烷 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以66%的产率得到2-(3-iodopropyl)-5-naphthalen-2-ylmethyl-[1,3,4]oxadiazole
  参考文献：
  名称：

  Halogen effects in Robinson–Gabriel type reaction of cyclopropanecarboxylic acid N′-substituted-hydrazides with PPh3/CX4

  摘要：

  We found that the reaction of cyclopropanecarboxylic acid N'- substituted -hydrazides with PPh3/CCl4 proceeded smoothly to give the corresponding normal Robinson-Gabriel type product 2-cyclopropyl-5-substituted-[1,3,4]-oxadiazoles in good yields. Using CBr4 or CI4 instead Of CCl4 in the above system, the ring opening of cyclopropane occurred after dehydration to give the corresponding 2-(3 -halopropyl) -5-substituted-[ 1, 3,4]-oxadiazoles (4 or 5) in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.048
• 作为产物：
  描述：

  2-萘-2-基乙酰肼 、 环丙基甲酰氯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以85%的产率得到cyclopropanecarboxylic acid N'-(2-naphthalen-2-yl-acetyl)-hydrazide
  参考文献：
  名称：

  Halogen effects in Robinson–Gabriel type reaction of cyclopropanecarboxylic acid N′-substituted-hydrazides with PPh3/CX4

  摘要：

  We found that the reaction of cyclopropanecarboxylic acid N'- substituted -hydrazides with PPh3/CCl4 proceeded smoothly to give the corresponding normal Robinson-Gabriel type product 2-cyclopropyl-5-substituted-[1,3,4]-oxadiazoles in good yields. Using CBr4 or CI4 instead Of CCl4 in the above system, the ring opening of cyclopropane occurred after dehydration to give the corresponding 2-(3 -halopropyl) -5-substituted-[ 1, 3,4]-oxadiazoles (4 or 5) in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.048

文献信息

• Halogen effects in Robinson–Gabriel type reaction of cyclopropanecarboxylic acid N′-substituted-hydrazides with PPh3/CX4
  作者：Yong-Hua Yang、Min Shi

  DOI：10.1016/j.tetlet.2005.07.048

  日期：2005.9

  We found that the reaction of cyclopropanecarboxylic acid N'- substituted -hydrazides with PPh3/CCl4 proceeded smoothly to give the corresponding normal Robinson-Gabriel type product 2-cyclopropyl-5-substituted-[1,3,4]-oxadiazoles in good yields. Using CBr4 or CI4 instead Of CCl4 in the above system, the ring opening of cyclopropane occurred after dehydration to give the corresponding 2-(3 -halopropyl) -5-substituted-[ 1, 3,4]-oxadiazoles (4 or 5) in good yields. (c) 2005 Elsevier Ltd. All rights reserved.