9-cyclopropyl-9H-carbazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-cyclopropyl-9H-carbazole
• 英文别名: 9-cyclopropylcarbazole；N-cyclopropylcarbazole；9-Cyclopropylcarbazole
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: LYHSHBMGIXFZMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-chlorocyclopropyl phenyl sulfoxide 、 lithium carbazolide 在 异丙基氯化镁 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以43%的产率得到9-cyclopropyl-9H-carbazole
  参考文献：
  名称：

  Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

  摘要：

  Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 degrees C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give alpha-ammo-substituted cyclopropylmagnesiums. The reaction of the a-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.080

文献信息

• Copper-Mediated <i>N</i>-Cyclopropylation of Azoles, Amides, and Sulfonamides by Cyclopropylboronic Acid
  作者：Sébastien Bénard、Luc Neuville、Jieping Zhu

  DOI：10.1021/jo801033y

  日期：2008.8.1

  Reaction of azoles, amides, and sulfonamides in dichloroethane with readily available cyclopropylboronic acid in the presence of copper acetate and sodium carbonate afforded the N-cyclopropyl derivatives in good to excellent yields.
• <i>N</i>-Cyclopropylation of Indoles and Cyclic Amides with Copper(II) Reagent
  作者：Takayuki Tsuritani、Neil A. Strotman、Yuhei Yamamoto、Masashi Kawasaki、Nobuyoshi Yasuda、Toshiaki Mase

  DOI：10.1021/ol800376f

  日期：2008.4.1

  Copper-mediated coupling reactions of cyclopropylboronic acid with indoles and cyclic amides are described. The process utilizes catalytic or stoichiometric amounts of copper(II) acetate, DMAP, and NaHMDS at 95 degrees C under an atmosphere containing oxygen. A variety of functional groups remain intact throughout the reaction.
• Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles
  作者：Tsuyoshi Satoh、Mariko Miura、Ken Sakai、Yoshimi Yokoyama

  DOI：10.1016/j.tet.2006.01.080

  日期：2006.4

  Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 degrees C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give alpha-ammo-substituted cyclopropylmagnesiums. The reaction of the a-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized. (c) 2006 Elsevier Ltd. All rights reserved.