1-(1,3-dioxolan-2-yl)-5-phenylpentan-3-ol | 346423-24-3

• 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: 1-(1,3-dioxolan-2-yl)-5-phenylpentan-3-ol
• CAS: 346423-24-3
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: DWJPJPDCCOEECC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,3-dioxolan-2-yl)-5-phenylpentan-3-ol 在 盐酸 、 偶氮二甲酸二异丙酯 、 氨 、 氢气 、 三苯基膦 、 sodium chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 2-(2-苯基乙基)吡咯烷
  参考文献：
  名称：

  The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships

  摘要：

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.021
• 作为产物：
  描述：

  苯丙醛 、 (2-(1,3-dioxolan-2-yl)ethyl)magnesium bromide 生成 1-(1,3-dioxolan-2-yl)-5-phenylpentan-3-ol
  参考文献：
  名称：

  The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships

  摘要：

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.021

文献信息

• Constructing Saturated Guanidinum Heterocycles by Cycloaddition of <i>N</i>-Amidinyliminium Ions with Indoles
  作者：Tyler K. Allred、Michael B. Shaghafi、Pan-Pan Chen、Quan Tran、K. N. Houk、Larry E. Overman

  DOI：10.1021/acs.orglett.1c02832

  日期：2021.10.1

  step by regio- and stereoselective [4 + 2]-cycloadditions of N-amidinyliminium ions with indoles or benzothiophene. In contrast to reactions of these heterodienes with alkenes, density functional theory (DFT) calculations show that these cycloadditions take place in a concerted asynchronous fashion. The [4 + 2]-cycloaddition of N-amidinyliminium ions (1,3-diaza-1,3-dienes) with indoles and benzothiophene

  我们报告说，结构复杂的胍杂环可以通过N-脒基亚胺离子与吲哚或苯并噻吩的区域和立体选择性 [4 + 2]-环加成反应一步制备。与这些异二烯与烯烃的反应相反，密度泛函理论 (DFT) 计算表明，这些环加成以协调的异步方式发生。在[4 + 2] -环的Ñ -amidinyliminium离子（1,3-二氮杂-1,3-二烯）与吲哚和苯并噻吩是独特的，作为与[4 + 2]的-cycloadditions N- acyliminium离子（1- oxa-3-aza-1,3-diene）显然是未知的。
• Synthesis of Polycyclic Guanidines by Cyclocondensation Reactions of <i>N</i>-Amidinyliminium Ions
  作者：Larry E. Overman、John P. Wolfe

  DOI：10.1021/jo0100998

  日期：2001.5.1

  A new method for the synthesis of polycyclic guanidines is described. The N-amidinyliminium ion generated from alpha-(phenylthio)amidine precursor 16 by reaction with Cu(OTf)(2) undergoes cyclocondensation with 1,3-dienes, styrenes, and beta -dicarbonyl compounds to give 1-iminohexahydropyrrolo[1,2-c]pyrimidines having side chains at C3 and C7. In all cases, major products have a cis relationship of the C7 side chain and angular C4a hydrogen, whereas C3 side chains are incorporated with lower stereoselectivity (dr = 2-5:1) in cyclocondensations with dienes and styrenes to give stereoisomer 39 as the major product.. In contrast to most cycloadditions of alkenes with N-acyliminium ions, cyclocondensations of alkenes with N-amidinyliminium ions proceed by a stepwise pathway. Cyclocondensation of the cognate ureido aminal 31 with styrene provides the rare 2-imino-5,6-dihydro-4H-1,3-oxazine derivative 32, rather than a pyrimidine as the major product. The high stereoselectivity observed in condensations of 16 with benzyl acetoacetate to afford Biginelli adduct 29 supports the intermediacy of N-amidinyliminium ions in related tethered Biginelli condensations of guanidines reported earlier from our laboratories.
• The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships
  作者：Michael B. Shaghafi、David G. Barrett、Francis S. Willard、Larry E. Overman

  DOI：10.1016/j.bmcl.2014.01.021

  日期：2014.2

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.