2,5,5-trimethyl-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c]chromene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,5,5-trimethyl-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c]chromene
• 英文别名: (2S,4aS,10bS)-2,5,5-trimethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]chromene
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: QTLDMKVNVOUSIV-VHRBIJSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-甲基-5-庚烯-2-醇 、 水杨醛 在 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 苯 为溶剂， 反应 4.0h， 以96%的产率得到2,5,5-trimethyl-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c]chromene
  参考文献：
  名称：

  水杨醛与不饱和醇一锅缩合反应合成 3,4,4a,10b-四氢-2H,5H-吡喃并[3,2-c][1]苯并吡喃

  摘要：

  在原甲酸三甲酯和催化量的对甲苯磺酸的存在下，水杨醛与 5-甲基-4-己烯-1-醇 (4a) 或 6-甲基-5-庚烯-2-醇 (4b) 在苯中反应rt 以高产率和完全立体选择性得到有角度稠合的反式-5,5-二甲基-3,4,4a,10b-四氢-2H,5H-吡喃并[3,2-c][1]苯并吡喃 (6)。

  DOI：

  10.1246/cl.1996.889

文献信息

• Modular Design of Chiral Conjugate-Base-Stabilized Carboxylic Acids: Catalytic Enantioselective [4 + 2] Cycloadditions of Acetals
  作者：Zhengbo Zhu、Minami Odagi、Nantamon Supantanapong、Weici Xu、Jaan Saame、Helmi-Ulrika Kirm、Khalil A. Abboud、Ivo Leito、Daniel Seidel

  DOI：10.1021/jacs.0c07212

  日期：2020.9.9

  Readily available 1,2-amino alcohols provide the framework for a new generation of chiral carboxylic acid catalysts that rival the acidity of the widely used chiral phosphoric acid catalyst (S)-TRIP. Covalently linked thiourea sites stabilize the carboxylate conjugate bases of these catalysts via anion-binding, an interaction that is largely responsible for the low pKa values. The utility of the new

  易于获得的 1,2-氨基醇为新一代手性羧酸催化剂提供了框架，其酸度可与广泛使用的手性磷酸催化剂 (S)-TRIP 的酸度相媲美。共价连接的硫脲位点通过阴离子结合稳定这些催化剂的羧酸盐共轭碱，这种相互作用是造成低 pKa 值的主要原因。新催化剂的效用在水杨醛衍生的缩醛与高烯丙醇和双烯丙醇的具有挑战性的 [4+2] 环加成的背景下进行了说明，以高度对映选择性的方式提供多环色满。
• Stereoselective Synthesis of Pyrano[3,2-<i>c</i>]benzopyrans via Intramolecular Cycloaddition of <i>o</i>-Quinonemethides Generated from Salicylaldehydes and Unsaturated Alcohols under Very Mild Conditions
  作者：Hidekazu Miyazaki、Kiyoshi Honda、Masatoshi Asami、Seiichi Inoue

  DOI：10.1021/jo991132h

  日期：1999.12.1

  Intramolecular [4 + 2] cycloaddition reaction of 6-(4-alkenyloxymethylene)-2,4-cyclohexadien-1-ones generated from the reaction between substituted salicylaldehydes and unsaturated alcohols under mild conditions was investigated. In general, the reaction furnished tricyclic compounds containing the pyranobenzopyran skeleton with trans-fused B/C ring in very good yields (Tables 1 and 2). Furthermore, geometry of the olefinic bond of the starting material is retained during the reaction.
• A simple and expeditious synthesis of 2,3,6-trisubstituted tetrahydropyrans through (3,5)-oxonium-ene cyclization using molecular iodine
  作者：N. Prudhvi Raju、B. Jagan Mohan Reddy、R. Anjibabu、K. Muralikrishna、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2013.04.104

  日期：2013.7

  A variety of aldehydes undergo a smooth coupling with 6-methylhept-5-en-2ol in the presence of molecular iodine to afford the 2,3,6-trisubstituted tetrahydropyrans in good yields through 3,5-oxonium-ene cyclization under mild and neutral conditions. This method is simple, convenient, and cost-effective. (C) 2013 Elsevier Ltd. All rights reserved.
• Diverse Cyclization Catalyzed by In(OTf)₃ for the Convergent Assembly of Substituted Tetrahydrofurans and Tetrahydropyrans
  作者：Teck-Peng Loh、Qi-Ying Hu、Kui-Thong Tan、Hin-Soon Cheng

  DOI：10.1021/ol016228o

  日期：2001.8.1

  [GRAPHICS]A novel In(OTf)(3)-catalyzed (3,5) oxonium-ene type cyclization for the facile construction of various multisubstituted tetrahydrofurans and tetrahydropyrans was successfully developed. Further mechanistic investigations unveiled an ln(OTf)(3)-catalyzed skeletal reorganization of the tetrahydrofuran to its thermodynamic isomer under thermal conditions.
• Diastereoselective Synthesis of Angularly Fused Pyranochromenes
  作者：Gakul Baishya、Barnali Sarmah、Nabajyoti Hazarika、Pranab Das

  DOI：10.1055/s-0034-1378831

  日期：——

  o-Quinonemethides generated by condensation of 6-methylhept-5-en-2-ol with various salicylaldehydes in the presence of 30 mol% of fluoroboric acid etherate or triflic acid undergo [4+2]-cycloaddition reaction in situ to afford angularly fused pyranochromene derivatives in good yields and excellent diastereoselectivities.