1-(2-propynyl)-1-cyclopentanecarboxylic acid | 1242265-30-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2-propynyl)-1-cyclopentanecarboxylic acid
• 英文别名: 1-(Prop-2-yn-1-yl)cyclopentane-1-carboxylic acid；1-prop-2-ynylcyclopentane-1-carboxylic acid
• CAS: 1242265-30-0
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: MUJVFRALWHJTRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-propynyl)-1-cyclopentanecarboxylic acid 、 2-amino-N'-phenylbenzohydrazide 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以84%的产率得到3a'-methyl-4'-(phenylamino)-3a',4'-dihydro-1'H-spiro[cyclopentane-1,2'-pyrrolo[1,2-a]quinazoline]-1',5'(3'H)-dione
  参考文献：
  名称：

  新型线性和成角稠合喹唑啉酮：通过金 (I) 催化的级联反应和抗癌活性合成

  摘要：

  通过开发金 (I) 催化的 2-氨基苯甲酰肼和炔酸之间的级联反应，建立了一种强大的基于库的新稠合喹唑啉酮方法。在体外将选定的化合物施用于肺 (A549) 和乳腺癌细胞 (MDA-MB-231 和 MCF-7)，发现其中一些成功地抑制了细胞增殖。

  DOI：

  10.1002/ejoc.201101822
• 作为产物：
  描述：

  methyl 1-(prop-2-yn-1-yl)cyclopentanecarboxylate 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以81%的产率得到1-(2-propynyl)-1-cyclopentanecarboxylic acid
  参考文献：
  名称：

  Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused Dihydrobenzimidazoles and Tetrahydroquinazolines

  摘要：

  A process involving gold(I)-catalyzed formal double hydroamination of alkynes, bearing a tethered carboxylic group, for the synthesis of fused dihydrobenzimidazoles and tetrahydroquinazolines has been developed. A series of transition metal catalysts have been screened for this transformation, and a catalyst system consisting of Ph3PAuCl (1 mol %) and AgOTf (1 mol %) was found to be the best. The procedure entails the reaction of easily accessible starting materials such as alkynoic acids and 1,2-diaminobenzenes/2-aminobenzylamines in the presence of the catalyst in 1,2-dichloroethane at 100 degrees C. In the case of alpha-substituted alkynoic acids, the corresponding products were obtained in high diastereoselectivities; the structure of the diastereomers has been unambiguously characterized by NMR techniques. The mechanism of the reaction is discussed, and the origin of the diastereoselectivities is addressed. It was observed that under the microwave irradiation conditions, the reaction time is significantly shortened (0.5 h).

  DOI：

  10.1021/jo1013228

文献信息

• Relay Catalytic Branching Cascade: A Technique to Access Diverse Molecular Scaffolds
  作者：Nitin T. Patil、Valmik S. Shinde、Balasubramanian Sridhar

  DOI：10.1002/anie.201208738

  日期：2013.2.18

  Skeletal diversity: The reactions of alkynoic acids (A, common type of substrates) with various scaffold‐building agents (B) under gold catalysis produce a series of multifunctional polyheterocyclic structures (see scheme). The approach enables the preparation of compound libraries with high skeletal diversity.

  骨骼多样性：在金催化下，炔酸（A，常见的底物类型）与各种支架构建剂（B）的反应产生了一系列多功能的多杂环结构（参见方案）。该方法能够制备具有高骨架多样性的化合物文库。
• NOUVEAUX DERIVES D'INDOLIZINE, LEUR PRÉPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：SANOFI

  公开号：EP2640724A1

  公开（公告）日：2013-09-25
• [EN] NOVEL INDOLIZINE DERIVATIVES, AND PREPARATION AND THERAPEUTIC USE THEREOF<br/>[FR] NOUVEAUX DERIVES D'INDOLIZINE, LEUR PRÉPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：SANOFI SA

  公开号：WO2012066234A1

  公开（公告）日：2012-05-24

  L'invention concerne des dérivés d'indolizine, de formule générale (I) dans laquelle A, B, m, W, n, et R2 sont tels que définis dans la revendication 1, ainsi que leur procédé de préparation et leur application en thérapeutique.
• Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused Dihydrobenzimidazoles and Tetrahydroquinazolines
  作者：Nitin T. Patil、Anil Kumar Mutyala、Pediredla G. V. V. Lakshmi、Balakrishna Gajula、Balasubramanian Sridhar、Gurava Reddy Pottireddygari、Tadikamalla Prabhakar Rao

  DOI：10.1021/jo1013228

  日期：2010.9.3

  A process involving gold(I)-catalyzed formal double hydroamination of alkynes, bearing a tethered carboxylic group, for the synthesis of fused dihydrobenzimidazoles and tetrahydroquinazolines has been developed. A series of transition metal catalysts have been screened for this transformation, and a catalyst system consisting of Ph3PAuCl (1 mol %) and AgOTf (1 mol %) was found to be the best. The procedure entails the reaction of easily accessible starting materials such as alkynoic acids and 1,2-diaminobenzenes/2-aminobenzylamines in the presence of the catalyst in 1,2-dichloroethane at 100 degrees C. In the case of alpha-substituted alkynoic acids, the corresponding products were obtained in high diastereoselectivities; the structure of the diastereomers has been unambiguously characterized by NMR techniques. The mechanism of the reaction is discussed, and the origin of the diastereoselectivities is addressed. It was observed that under the microwave irradiation conditions, the reaction time is significantly shortened (0.5 h).
• New Linearly and Angularly Fused Quinazolinones: Synthesis through Gold(I)-Catalyzed Cascade Reactions and Anticancer Activities
  作者：Nitin T. Patil、Pediredla G. V. V. Lakshmi、Balasubramanian Sridhar、Sujata Patra、Manika Pal Bhadra、Chitta Ranjan Patra

  DOI：10.1002/ejoc.201101822

  日期：2012.3

  A robust library-based approach to new fused quinazolinones by the development of gold(I)-catalyzed cascade reactions between 2-aminobenzohydrazides and alkynoic acids is documented. Selected compounds were administered to lung (A549) and breast cancer cells (MDA-MB-231 and MCF-7) in vitro and it was found that some successfully inhibited cell proliferation.

  通过开发金 (I) 催化的 2-氨基苯甲酰肼和炔酸之间的级联反应，建立了一种强大的基于库的新稠合喹唑啉酮方法。在体外将选定的化合物施用于肺 (A549) 和乳腺癌细胞 (MDA-MB-231 和 MCF-7)，发现其中一些成功地抑制了细胞增殖。