2-(cyclopropylmethyl)aniline | 1224733-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(cyclopropylmethyl)aniline
• 英文别名: 2-aminobenzylcyclopropane
• CAS: 1224733-72-5
• 化学式: C₁₀H₁₃N
• mdl: MFCD19215715
• 分子量: 147.22
• InChiKey: JAMNIFGXCWPBTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-(cyclopropylmethyl)aniline 在 [Rh(cod)2]BARF 、 富马酸二甲酯 、 氢气 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 苯甲腈 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 100.0~120.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 以79%的产率得到3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one
  参考文献：
  名称：

  非活化环丙烷的氮导向 C-C 键活化羰基化 N-杂环化

  摘要：

  在 Rh 催化条件下，仲胺和苯胺作为导向基团促进非活化环丙烷的区域选择性 C-C 键活化。由此产生的氨基稳定的罗丹环在形成具有挑战性的七元和八元内酰胺的过程中经历了羰基化 C-N 键的形成。这些过程代表了在反应设计中利用非活化环丙烷的 C-C 键氧化加成的罕见例子。

  DOI：

  10.1021/jacs.2c02921
• 作为产物：
  描述：

  1-(环丙基甲基)-2-硝基苯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以86%的产率得到2-(cyclopropylmethyl)aniline
  参考文献：
  名称：

  4H-3,1-benzoxazines from benzyl cyclopropanes. First example of acid catalyzed rearrangement in ortho-substituted benzylcyclo-propanes

  摘要：

  The synthesis of 2-N-acylamino-substituted benzylcyclopropanes has been carried out. It was established that under the action of acids 2-N-acylamino-substituted benzylcyclopropanes are rearranged into the corresponding 4H-3,1-benzoxazines and not into the expected 3,1-benzoxazepines. It was shown that a similar type of rearrangement is also characteristic for 2-N-acylamino-substituted allylbenzenes.

  DOI：

  10.1007/s10593-009-0400-x

文献信息

• BIS AROMATIC COMPOUNDS FOR USE AS LTC4 SYNTHASE INHIBITORS
  申请人：Biolipox AB

  公开号：EP2406223A2

  公开（公告）日：2012-01-18
• [EN] GLYCORTICOID RECEPTOR ANTAGONISTS FOR TREATMENT OF DIABETES<br/>[FR] ANTAGONISTES DE RECEPTEURS DE GLUCOCORTICOIDES POUR TRAITEMENT DE DIABETES
  申请人：ABBOTT LAB

  公开号：WO2002070507A2

  公开（公告）日：2002-09-12

  Compounds of formula (I) are useful for treating type (II) diabetes, obesity, hyperglycemia, inadequate glucose clearance, hyperinsulinemia, hypertriglyceridemia, and high-circulating glucocorticoid levels, preparations of the compounds, compositions containing the compounds, and methods of treatment using the compounds.
• [EN] BIS AROMATIC COMPOUNDS FOR USE AS LTC4 SYNTHASE INHIBITORS<br/>[FR] COMPOSÉS BIS AROMATIQUES DESTINÉS À UTILISATION EN TANT QU'INHIBITEURS DE LTC4 SYNTHASE
  申请人：BIOLIPOX AB

  公开号：WO2010103297A2

  公开（公告）日：2010-09-16

  There is provided compounds of formula (I), wherein Y, ring A1 D1, D2a, D2b, D3, L1, Y1, L3 and Y3 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of leukotriene C4 synthase is desired and/or required, and particularly in the treatment of a respiratory disorder and/or inflammation.
• 4H-3,1-benzoxazines from benzyl cyclopropanes. First example of acid catalyzed rearrangement in ortho-substituted benzylcyclo-propanes
  作者：E. V. Trofimova、B. P. Archegov、A. N. Fedotov、R. A. Gazzaeva、S. S. Mochalov、N. S. Zefirov

  DOI：10.1007/s10593-009-0400-x

  日期：2009.9

  The synthesis of 2-N-acylamino-substituted benzylcyclopropanes has been carried out. It was established that under the action of acids 2-N-acylamino-substituted benzylcyclopropanes are rearranged into the corresponding 4H-3,1-benzoxazines and not into the expected 3,1-benzoxazepines. It was shown that a similar type of rearrangement is also characteristic for 2-N-acylamino-substituted allylbenzenes.
• Carbonylative N-Heterocyclization via Nitrogen-Directed C–C Bond Activation of Nonactivated Cyclopropanes
  作者：Adam D. J. Calow、David Dailler、John F. Bower

  DOI：10.1021/jacs.2c02921

  日期：2022.6.29

  as directing groups to facilitate regioselective C–C bond activation of nonactivated cyclopropanes. The resulting amino-stabilized rhodacycles undergo carbonylative C–N bond formation en route to challenging seven- and eight-membered lactams. The processes represent rare examples where C–C bond oxidative addition of nonactivated cyclopropanes is exploited in reaction design.

  在 Rh 催化条件下，仲胺和苯胺作为导向基团促进非活化环丙烷的区域选择性 C-C 键活化。由此产生的氨基稳定的罗丹环在形成具有挑战性的七元和八元内酰胺的过程中经历了羰基化 C-N 键的形成。这些过程代表了在反应设计中利用非活化环丙烷的 C-C 键氧化加成的罕见例子。