4-cyclopentyl-1-butyne | 141345-07-5

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 4-cyclopentyl-1-butyne
• 英文别名: (But-3-yn-1-yl)cyclopentane；but-3-ynylcyclopentane
• CAS: 141345-07-5
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: OMYWKSZLTXAMIG-UHFFFAOYSA-N

物化性质

• 沸点：
  156.0±9.0 °C(Predicted)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-cyclopentyl-1-butyne 在 正丁基锂 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 silver(I) acetate 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  使用 SEt 作为无痕导向基团的炔烃光催化磺酰基碳环化：获得环戊烯和茚

  摘要：

  开发了使用 SEt 作为无痕导向基团的末端炔烃的光催化磺酰基碳环化，提供了从容易获得的起始材料中轻松获得高度取代的环戊烯和茚的方法。它代表了全碳系统的反鲍德温 5-endo-trig 自由基环化的新进展，这可能对快速构建五元碳环很有价值。

  DOI：

  10.1002/anie.202110864
• 作为产物：
  描述：

  2-环戊基乙醇 在 硫酸 、 氢溴酸 作用下， 以 二甲基亚砜 为溶剂， 反应 11.0h， 生成 4-cyclopentyl-1-butyne
  参考文献：
  名称：

  Nucleosides and nucleotides. 107. 2-(Cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects

  摘要：

  Adenosine receptor-binding profiles in rat brain tissues and antihypertensive effects in spontaneously hypertensive rats (SHR) of a series of 2-(cycloalkylalkynyl)adenosines (2-CAAs) and their congeners are described. The structure-activity relationship of this series of compounds is discussed, focusing on the length of the alkynyl side chain and bulkiness of the terminal cycloalkyl substituents in terms of binding activity and cardiovascular effects. All the 2-CAAs had a preferential affinity for A2 receptors. Of these derivatives, 2-(3-cyclopentyl-1-propyn-1-yl)adenosine (10b) exhibited the most selective affinity for A2 receptors (K(i) ratio: A1/A2 = 70) on the basis of receptor binding. In the C-2 binding region of adenosine, compounds often have potent and/or selective A2 activity from introduction of an acetylenic group at the C-2 position followed by one methylene residue further followed by a hydrophobic substituent such as a cycloalkyl ring at the terminal position of the alkynyl side chain. Intravenous injection of 10b up to 100-mu-g/kg had a potent hypotensive effect without a marked decrease in heart rate in anesthetized SHR. Compounds 10j-s, with a hydroxyl group in the C-3" position of the alkynyl side chain, had a potent affinity for both A1 and A2 receptors, but they were not highly selective for A2 receptors. These compounds caused a marked bradycardia upon intravenous administration in anesthetized SHR. Oral administration of 10b (0.1-1 mg/kg) had a potent and long-lasting antihypertensive effect in conscious SHR.

  DOI：

  10.1021/jm00090a017

文献信息

• Alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders
  申请人：Scott Ian Leslie

  公开号：US20090062353A1

  公开（公告）日：2009-03-05

  Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.

  本发明提供了炔基苯衍生物化合物，其药物组成物及使用该化合物和组成物治疗眼科疾病和疾患的方法，例如老年性黄斑变性和斯塔格特病。
• Alkynyl Phenyl Derivative Compounds for Treating Ophthalmic Diseases and Disorders
  申请人：Scott Ian Leslie

  公开号：US20120004269A1

  公开（公告）日：2012-01-05

  Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.

  本发明提供了炔基苯衍生物化合物、其制药组合物以及使用该化合物和组合物治疗眼科疾病和障碍的方法，例如老年性黄斑变性和Stargardt病。
• ALKYNYL PHENYL DERIVATIVE COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS
  申请人：Scott Ian Leslie

  公开号：US20130018077A1

  公开（公告）日：2013-01-17

  Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.

  本发明提供了炔基苯衍生物化合物、其制药组合物以及使用该化合物和组合物治疗眼科疾病和疾病的方法，例如老年性黄斑变性和Stargardt病。
• Photocatalytic Sulfonylcarbocyclization of Alkynes Using SEt as a Traceless Directing Group: Access to Cyclopentenes and Indenes
  作者：Yulu Zhou、Yizhou Qin、Qinggui Wang、Zuxiao Zhang、Gangguo Zhu

  DOI：10.1002/anie.202110864

  日期：2022.1.3

  A photocatalytic sulfonylcarbocyclization of terminal alkynes using SEt as a traceless directing group is developed, providing a facile access to highly substituted cyclopentenes and indenes from readily available starting materials. It represents a new advance on anti-Baldwin 5-endo-trig radical cyclization of all-carbon systems, which may be valuable for the fast construction of five-membered carbocycles

  开发了使用 SEt 作为无痕导向基团的末端炔烃的光催化磺酰基碳环化，提供了从容易获得的起始材料中轻松获得高度取代的环戊烯和茚的方法。它代表了全碳系统的反鲍德温 5-endo-trig 自由基环化的新进展，这可能对快速构建五元碳环很有价值。
• Nucleosides and nucleotides. 107. 2-(Cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects
  作者：Toichi Abiru、Takanori Miyashita、Yohko Watanabe、Toyofumi Yamaguchi、Haruhiko Machida、Akira Matsuda

  DOI：10.1021/jm00090a017

  日期：1992.6

  Adenosine receptor-binding profiles in rat brain tissues and antihypertensive effects in spontaneously hypertensive rats (SHR) of a series of 2-(cycloalkylalkynyl)adenosines (2-CAAs) and their congeners are described. The structure-activity relationship of this series of compounds is discussed, focusing on the length of the alkynyl side chain and bulkiness of the terminal cycloalkyl substituents in terms of binding activity and cardiovascular effects. All the 2-CAAs had a preferential affinity for A2 receptors. Of these derivatives, 2-(3-cyclopentyl-1-propyn-1-yl)adenosine (10b) exhibited the most selective affinity for A2 receptors (K(i) ratio: A1/A2 = 70) on the basis of receptor binding. In the C-2 binding region of adenosine, compounds often have potent and/or selective A2 activity from introduction of an acetylenic group at the C-2 position followed by one methylene residue further followed by a hydrophobic substituent such as a cycloalkyl ring at the terminal position of the alkynyl side chain. Intravenous injection of 10b up to 100-mu-g/kg had a potent hypotensive effect without a marked decrease in heart rate in anesthetized SHR. Compounds 10j-s, with a hydroxyl group in the C-3" position of the alkynyl side chain, had a potent affinity for both A1 and A2 receptors, but they were not highly selective for A2 receptors. These compounds caused a marked bradycardia upon intravenous administration in anesthetized SHR. Oral administration of 10b (0.1-1 mg/kg) had a potent and long-lasting antihypertensive effect in conscious SHR.