3-chloro-N-cyclopropylaniline | 1368173-78-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-chloro-N-cyclopropylaniline
• 英文别名: 3-chloro-N-cyclopropylbenzenamine
• CAS: 1368173-78-7
• 化学式: C₉H₁₀ClN
• 分子量: 167.638
• InChiKey: BOFNFAVPFUOZNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  methyl phenylethynyl sulfone 、 3-chloro-N-cyclopropylaniline 在 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline bis[(2-diphenyl-phosphino)phenyl]ether copper(I) hexafluorophosphate 作用下， 以 甲苯 为溶剂， 以75 %的产率得到3-chloro-N-(3-(methylsulfonyl)-2-phenylcyclopent-2-en-1-yl)aniline
  参考文献：
  名称：

  P/N-杂配 Cu(I)-光敏剂催化的 [3 + 2] 氨基环丙烷和功能化炔烃的区域特异性环化

  摘要：

  我们在这里报告了在光氧化还原催化条件下，由P / N -杂配 Cu(I) 光敏剂实现的氨基环丙烷和各种功能化炔烃之间的区域特异性 [3 + 2] 环化。因此，可以实现 3-氨基环戊烯衍生物的发散结构，包括甲基磺酰基-、芳基磺酰基-、氯-、酯-和三氟甲基-官能化的氨基环戊烯，具有高区域选择性、广泛的底物相容性以及温和和环境友好的反应条件等优点。

  DOI：

  10.1021/acs.joc.2c02138
• 作为产物：
  描述：

  2-(3-chlorophenoxy)-N-cyclopropylacetamide 在 potassium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 甲苯 为溶剂， 以71%的产率得到3-chloro-N-cyclopropylaniline
  参考文献：
  名称：

  An Efficient Synthesis of N-Cyclopropylanilines by a Smiles Rearrangement

  摘要：

  Treatment of 2-chloro-N-cyclopropylacetamide with phenols gave the corresponding 2-aryloxy-N-cyclopropylacetamides, which on treatment with a base gave the corresponding N-cyclopropylanilines.

  DOI：

  10.1055/s-0032-1318389

文献信息

• Inhibitors of Ion Channels
  申请人：Marron Brian Edward

  公开号：US20130072471A1

  公开（公告）日：2013-03-21

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-gated sodium channels. More particularly, the invention provides substituted aryl sulfonamides, compositions comprising these compounds, as well as methods of using these compounds or compositions in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrence of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a voltage-gated sodium channel.

  本发明提供了在通过抑制电压门控钠通道中的钠离子流来治疗疾病方面有用的化合物、组合物和方法。更具体地，本发明提供了取代芳基磺酰胺、包含这些化合物的组合物，以及使用这些化合物或组合物治疗中枢或外周神经系统疾病，特别是疼痛和慢性疼痛的方法，通过阻断与所示条件的发生或复发相关的钠通道来实现。本发明的化合物、组合物和方法特别适用于通过抑制电压门控钠通道中的离子流来治疗神经病性或炎症性疼痛。
• INHIBITORS OF ION CHANNELS
  申请人：Marron Brian Edward

  公开号：US20090143358A1

  公开（公告）日：2009-06-04

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-gated sodium channels. More particularly, the invention provides substituted aryl sulfonamides, compositions comprising these compounds, as well as methods of using these compounds or compositions in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrence of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a voltage-gated sodium channel.

  本发明提供了化合物、组合物和方法，通过抑制电压门控钠通道中的钠离子流来治疗疾病。更具体地，本发明提供了取代芳基磺酰胺、包含这些化合物的组合物，以及使用这些化合物或组合物治疗中枢或外周神经系统疾病，特别是疼痛和慢性疼痛的方法，通过阻止与所示疾病的发生或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制电压门控钠通道中的离子流来治疗神经病理性或炎症性疼痛。
• Room-Temperature CuI-Catalyzed <i>N</i>-Arylation of Cyclopropylamine
  作者：Peng Hong、Xinhai Zhu、Xin Lai、Zinan Gong、Manna Huang、Yiqian Wan

  DOI：10.1021/acs.joc.3c01357

  日期：2024.1.5

  A general and efficient CuI/N-carbazolyl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the N-arylation of cyclopropylamine using aryl bromides at room temperature. Herein, 5 mol % CuI and 5 mol % of the ligand were used to synthesize N-aryl cyclopropylamines in moderate to excellent yields. This protocol was scaled up to produce the desired product at gram levels and has been generalized

  开发了一种通用且高效的 CuI/ N-咔唑基-1H-吡咯-2-碳酰肼催化剂体系，用于在室温下使用芳基溴进行环丙胺的N-芳基化。在此，使用 5 mol% CuI 和 5 mol% 配体以中等至优异的产率合成N-芳基环丙胺。该方案被放大以生产克级的所需产物，并已推广到室温下芳基溴和胺之间的 C-N 偶联。
• Synthesis of 3-aminotetrahydro-1<i>H</i>-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides
  作者：Xiaofei Zhang、Yao Wang、Jiaxin Liu、Chengpeng Tian、Xiang Li、Pan Xie、Zhenyu Zhu、Tuanli Yao

  DOI：10.1039/d3cc04674e

  日期：——

  cyclopropylanilines is reported. This cascade radical reaction constructs two new C–C bonds and two rings to afford 3-aminotetrahydro-1H-carbazols with high atom and step economy. The mechanism is rationalized as involving sequential distonic radical cation formation/isocyanide insertion/5-exo-trig cyclization/intramolecular iminium ion addition/tautomerization.

  据报道，2-烯基芳基异氰化物和环丙基苯胺之间发生可见光诱导的环加成反应。这种级联自由基反应构建了两个新的 C-C 键和两个环，得到具有高原子和步骤经济性的 3-氨基四氢-1 H-咔唑。该机制被合理化为涉及顺序双张力自由基阳离子形成/异氰化物插入/5-外-三环化/分子内亚胺离子加成/互变异构化。
• Iron(II)-Catalyzed Radical [3 + 2] Cyclization of <i>N</i>-Aryl Cyclopropylamines for the Synthesis of Polyfunctionalized Cyclopentylamines
  作者：Shuo Lv、Wen-Feng Xu、Ting-You Yang、Ming-Xing Lan、Ren-Xu Xiao、Xue-Qing Mou、Yong-Zheng Chen、Bao-Dong Cui

  DOI：10.1021/acs.orglett.4c00757

  日期：2024.4.19

  A facile iron(II)-catalyzed radical [3 + 2] cyclization of N-aryl cyclopropylamines with various alkenes to access the structurally polyfunctionalized cyclopentylamine scaffolds has been developed. Using low-cost FeCl2·4H2O as catalyst, N-aryl cyclopropylamines could be utilized to react with a wide range of alkenes including exocyclic/acyclic terminal alkenes, cycloalkenes, alkenes from the natural-occurring

  已经开发出一种简单的铁(II)催化的N-芳基环丙胺与各种烯烃的自由基[3+2]环化，以获得结构上多官能化的环戊胺支架。使用低成本的FeCl 2 ·4H 2 O作为催化剂， N-芳基环丙胺可用于与多种烯烃反应，包括环外/无环末端烯烃、环烯烃、天然化合物的烯烃（香豆内酯、木香内酯）、和已知药物（布洛芬、 L-苯丙氨酸、氟比洛芬），以通常良好的产率和非对映选择性获得与不同有用基序融合的各种环戊胺。该方案的亮点还在于无需额外的氧化剂、无碱、EtOH为溶剂、克级合成以及合成产物的进一步多样化转化。更重要的是，基于机理研究实验，提出了铁（II）介导的氢自由基解离途径。