顺式-1-氨基-4-氯-2-丁烯 | 54880-27-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 顺式-1-氨基-4-氯-2-丁烯
• 英文名称: (Z)-4-chlorobut-2-en-1-amine hydrochloride
• 英文别名: cis-1-amino-4-chloro-2-butene；cis-4-chloro-2 butenylamine；cis-4-chloro-2-butenylamine；4-chloro-but-2c-enylamine；1-Amino-4-chlor-but-2c-en；4-Chlor-but-2c-enylamin；(2Z)-4-chloro-2-buten-1-amine；(Z)-4-chlorobut-2-en-1-amine
• CAS: 54880-27-2
• 化学式: C₄H₈ClN
• 分子量: 105.567
• InChiKey: DYUZZXXUVYQTQX-UPHRSURJSA-N

物化性质

• 沸点：
  172.5±28.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  顺式-1,4-二氯-2-丁烯	Z-1,4-dichlorobutene	1476-11-5	C4H6Cl2	124.998

反应信息

• 作为反应物：
  描述：

  顺式-1-氨基-4-氯-2-丁烯 、 二碳酸二叔丁酯 在 potassium carbonate 作用下， 以45%的产率得到N-Boc-3-吡咯啉
  参考文献：
  名称：

  Practical One-Pot and Large-Scale Synthesis of N-(tert-Butyloxycarbonyl)-3-pyrroline

  摘要：

  N-(tert-Butyloxycarbonyl)-3-pyrroline was prepared with high purity in large scale starting from cis-1,4-dichloro-2-butene via delepine reaction and subsequent cyclization in the presence of potassium carbonate followed by N-Boc protection in methanol. Judicious selection of base and solvent led to the use of a single solvent, i.e., methanol, for cyclization as well as for N-Boc protection to render the one-pot process from compound 2 more practical and greener than the stepwise version.

  DOI：

  10.1021/op8003037
• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 乌洛托品 在 氯仿 作用下， 生成 顺式-1-氨基-4-氯-2-丁烯
  参考文献：
  名称：

  Marszak-Fleury, Annales de Chimie (Cachan, France), 1958, vol. <13>3, p. 656,676

  摘要：

  DOI：

文献信息

• Synthesis of Novel Tetrahydroisoquinoline CXCR4 Antagonists with Rigidified Side-Chains
  作者：Edgars Jecs、Eric J. Miller、Robert J. Wilson、Huy H. Nguyen、Yesim A. Tahirovic、Brook M. Katzman、Valarie M. Truax、Michelle B. Kim、Katie M. Kuo、Tao Wang、Chi S. Sum、Mary E. Cvijic、Gretchen M. Schroeder、Lawrence J. Wilson、Dennis C. Liotta

  DOI：10.1021/acsmedchemlett.7b00406

  日期：2018.2.8

  potent TIQ15-derived CXCR4 antagonists is reported. In this investigation, the TIQ15 side-chain was constrained to improve its drug properties. The cyclohexylamino congener 15a was found to be a potent CXCR4 inhibitor (IC50 = 33 nM in CXCL12-mediated Ca2+ flux) with enhanced stability in liver microsomes and reduced inhibition of CYP450 (2D6). The improved CXCR4 antagonist 15a has potential therapeutic

  报道了有效的TIQ15衍生的CXCR4拮抗剂的结构活性关系研究。在这项研究中，TIQ15侧链被限制以改善其药物特性。发现环己基氨基同源物15a是有效的CXCR4抑制剂（在CXCL12介导的Ca 2+通量中IC 50 = 33 nM ），在肝微粒体中的稳定性增强，并且对CYP450（2D6）的抑制作用降低。改进的CXCR4拮抗剂15a具有作为单药或联合抗癌疗法的潜在治疗应用。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006020415A1

  公开（公告）日：2006-02-23

  The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind specifically to the chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 and/or CCR5 of a target cell.

  本发明提供了一种新型化合物，表现出对目标细胞免受HIV感染的保护效果，其特异地结合趋化因子受体，并影响自然配体或趋化因子与目标细胞的受体（如CXCR4和/或CCR5）的结合。
• A novel solid-phase synthesis of cyclic guanidines
  作者：Vladimir Y. Vvedensky、Boris V. Rogovoy、Alexander S. Kiselyov、Alexandre V. Ivachtchenko

  DOI：10.1016/j.tetlet.2005.10.039

  日期：2005.12

  We have developed a robust solid-phase approach to cyclic guanidines based on the Staudinger protocol. The synthetic sequence involves the reaction of the immobilized aza-Wittig reagents derived from the respective azidobenzoic acids with bifunctional amines. Convenient isolation and good yields of the desired products (34–84%) along with the diversity of the targeted molecules are distinctive features

  我们已经基于Staudinger协议开发了一种强大的固相方法制备环胍。合成顺序涉及衍生自各自叠氮苯甲酸的固定化aza-Wittig试剂与双官能胺的反应。方便的分离和所需产物的良好收率（34–84％）以及目标分子的多样性是所得文库的显着特征。
• Chemical Compounds
  申请人：Gudmundsson Kristjan

  公开号：US20080096861A1

  公开（公告）日：2008-04-24

  The present invention provides compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind to chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 of a target cell.

  本发明提供了一种化合物，它以结合趋化因子受体的方式对目标细胞表现出对HIV感染的保护作用，并且影响天然配体或趋化因子与目标细胞的CXCR4等受体的结合。
• Practical One-Pot and Large-Scale Synthesis of <i>N</i>-(<i>tert</i>-Butyloxycarbonyl)-3-pyrroline
  作者：Tammana Rajesh、Shaik Abdul Azeez、Erragunta Naresh、Gutta Madhusudhan、Kagga Mukkanti

  DOI：10.1021/op8003037

  日期：2009.5.15

  N-(tert-Butyloxycarbonyl)-3-pyrroline was prepared with high purity in large scale starting from cis-1,4-dichloro-2-butene via delepine reaction and subsequent cyclization in the presence of potassium carbonate followed by N-Boc protection in methanol. Judicious selection of base and solvent led to the use of a single solvent, i.e., methanol, for cyclization as well as for N-Boc protection to render the one-pot process from compound 2 more practical and greener than the stepwise version.