2,2-dimethyl-3,4,6,7-tetrahydro-2H-cyclopenta[b]pyran-5-one | 1260424-80-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 2,2-dimethyl-3,4,6,7-tetrahydro-2H-cyclopenta[b]pyran-5-one
• 英文别名: 2,2-dimethyl-3,4,6,7-tetrahydrocyclopenta[b]pyran-5(2H)-one；2,2-Dimethyl-3,4,6,7-tetrahydrocyclopenta[b]pyran-5-one；2,2-dimethyl-3,4,6,7-tetrahydrocyclopenta[b]pyran-5-one
• CAS: 1260424-80-3
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: NLTNHHRGGNOPSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-bis(3-methylbut-2-en-1-yl)cyclopentane-1,3-dione 在 aluminum (III) chloride 作用下， 以 1,4-二氧六环 为溶剂， 以70%的产率得到2,2-dimethyl-3,4,6,7-tetrahydro-2H-cyclopenta[b]pyran-5-one
  参考文献：
  名称：

  New chemical access for pyran core embedded derivatives from bisalkenylated 1,3-diketones and 1,3-diketoesters via tandem C-dealkenylation and cyclization

  摘要：

  New chemical access has been developed for the synthesis of pyran core embedded derivatives from 1,3-diketones and 1,3-diketoesters, in which the active methylene group of 1,3-diketone or 1,3-diketoester was alkenylated with three equivalents of alkenyl bromides in presence NaH to give bisalkenyl 1,3-diketones or 1,3-diketoesters and the resultant bisalkenyl 1,3-diketones or 1,3-diketoesters were reacted with AlCl3 at room temperature to furnish pyran core embedded derivatives in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.030

文献信息

• Isoprene: A Promising Coupling Partner in C–H Functionalizations
  作者：Qing-An Chen、Wei-Song Zhang、Yan-Cheng Hu

  DOI：10.1055/s-0040-1707172

  日期：2020.10

  basic industrial feedstock isoprene is an ideal alternative precursor. However, given that electronically unbiased isoprene might undergo six possible addition modes in the coupling reactions, it is difficult to control the selectivity. This article summarizes the strategies we have developed to achieve regioselective C–H functionalizations of isoprene under transition-metal and acid catalysis. 1 Introduction

  五碳二甲基烯丙基单元，如异戊二烯和反异戊二烯，广泛分布于天然吲哚生物碱和萜类化合物中。在传统方法中，这些有价值的基序通常来自带有离去基团的底物，但这些过程伴随着化学计量副产物的产生。从经济和环境的角度来看，基本工业原料异戊二烯是理想的替代前体。然而，考虑到电子无偏异戊二烯在偶联反应中可能经历六种可能的加成模式，很难控制选择性。本文总结了我们为在过渡金属和酸催化下实现异戊二烯的区域选择性 C-H 功能化而开发的策略。
• In(OTf)₃-catalysed easy access to dihydropyranocoumarin and dihydropyranochromone derivatives
  作者：Naouel Boufroua、Elisabet Dunach、Fabien Fontaine-Vive、Samia Achouche-Bouzroura、Sophie Poulain-Martini

  DOI：10.1039/d0nj00080a

  日期：——

  Allylation/cyclization of β-ketolactone-type heterocyclic compounds, under In(OTf)₃-catalysis, for the construction of biologically active dihydropyranocoumarin and dihydropyranochromone derivatives.

  β-酮内酯类杂环化合物的烯丙基化/环化反应，在In(OTf)₃催化下进行，用于构建具有生物活性的二氢吡喃香豆素和二氢吡喃色酮衍生物。
• Acid-catalyzed chemoselective C- and O- prenylation of cyclic 1,3-diketones
  作者：Ying Li、Yan-Cheng Hu、Ding-Wei Ji、Wei-Song Zhang、Gu-Cheng He、Yu-Feng Cong、Qing-An Chen

  DOI：10.1016/s1872-2067(20)63575-6

  日期：2020.9

  Abstract The chemoselective C- and O-prenylation of cyclic 1,3-diketones was achieved by tuning the prenyl source and catalyst. In the presence of the solid acid Nafion, the coupling of 1,3-cyclohexanediones with isoprene gave C-prenylated 5-chromenones. Alternatively, using prenol as the substrate with the Lewis acid AlCl3 as the catalyst resulted in the exclusive O-prenylation of 1,3-cyclohexanediones

  摘要 通过调整异戊二烯源和催化剂，实现了环状 1,3-二酮的化学选择性 C-和 O-异戊二烯化。在固体酸 Nafion 的存在下，1,3-环己二酮与异戊二烯的偶联得到 C-异戊二烯化的 5-色酮。或者，使用异戊烯醇作为底物，路易斯酸 AlCl3 作为催化剂导致 1,3-环己二酮的专属 O-异戊二烯化。值得注意的是，所得产品可以很容易地进行芳构化，以提供难以制备的异戊二烯化间苯二酚。我们的方法具有高度选择性、原子经济性、操作简单、易于扩展，并且在整个有机合成中具有潜在应用。