5,8-二甲氧基-2,2-二甲基-2H-色烯 | 113949-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5,8-二甲氧基-2,2-二甲基-2H-色烯
• 英文名称: 2,2-dimethyl-5,8-dimethoxy-2H-1-benzopyrane
• 英文别名: 5,8-dimethoxy-2,2-dimethyl-2H-chromene；2,2-dimethyl-5,8-dimethoxychromene；5,8-dimethoxy-2,2-dimethylchromene
• CAS: 113949-29-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: SZTFORJKIVHMFP-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  328.1±42.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909199090

反应信息

• 作为反应物：
  描述：

  5,8-二甲氧基-2,2-二甲基-2H-色烯 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以66%的产率得到2,2-dimethyl-5,8-dihydro-2H-1-benzopyran-5,8-dione
  参考文献：
  名称：

  Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone

  摘要：

  A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.

  DOI：

  10.1021/acs.orglett.9b00090
• 作为产物：
  描述：

  methyl (E)-3-(2,5-dimethoxyphenyl)acrylate 在 萘-1,4-二腈 、 magnesium 作用下， 以 水 、 乙腈 为溶剂， 反应 2.67h， 生成 5,8-二甲氧基-2,2-二甲基-2H-色烯
  参考文献：
  名称：

  Synthetic application of photoinduced single electron transfer reactions: a convenient synthetic approach for the 2,2-dimethyl-2H-chromene system

  摘要：

  DOI：

  10.1021/jo00245a047

文献信息

• Total synthesis of seco-lateriflorone
  作者：Eric J Tisdale、Binh G Vong、Hongmei Li、Sun Hee Kim、Chinmay Chowdhury、Emmanuel A Theodorakis

  DOI：10.1016/s0040-4020(03)00862-7

  日期：2003.8

  convergent strategy toward the synthesis of lateriflorone (5) is described. Our approach is based on biosynthetic considerations and draws on a sequence of prenylation, oxygenation and Claisen reactions for the construction of chromenequinone 6, and a tandem Claisen/Diels–Alder reaction cascade for the synthesis of caged tricycle 7. Union of fragments 6 and 7 led to the synthesis of seco-lateriflorone (49)

  描述了一种趋向于合成lateiflorone（5）的策略。我们的方法是基于生物合成的考虑，并利用一系列的异戊烯化，氧化和克莱森反应来构建亚甲基苯醌6，以及串联的克莱森/狄尔斯-阿尔德反应级联反应来合成笼型三轮车7。片段的联盟6和7导致的合成开环-lateriflorone（49）。
• Studies of chromenes. Part 9. Syntheses of chromenequinones
  作者：Philip E. Brown、Robert A. Lewis、Mark A. Waring

  DOI：10.1039/p19900002979

  日期：——

  Syntheses of 2,2-dimethylchromene-5,8-quinone, 2,2-dimethylchromene-6,7-quinone, and 6,7-dimethoxy-2,2-dimethylchromene-5,8-quinone are described. Being easily bioreducible to electron-rich chromenes these compounds, and their oxirane derivatives, are of interest as possible anti-tumour alkylating agents.

  描述了2，2-二甲基色烯-5，8-醌，2，2-二甲基色烯-6，7-醌和6，7-二甲氧基-2，2-二甲基色烯-5，8-醌的合成。这些化合物及其环氧乙烷衍生物易于被富电子的二烯生物还原，因此作为可能的抗肿瘤烷基化剂受到关注。
• Synthesis of (<i>S</i>)-4-hydroxy-α-lapachone and biotransformation of some 4-chromanones by <i>Mortierella</i><i>isabellina</i> ATCC 42613
  作者：Herbert L. Holland、Jia Qi、T. Samuel Manoharan

  DOI：10.1139/v95-174

  日期：1995.9.1

  1-Methoxy-2-naphthol was converted by MOM ether formation, lithiation at C-3, reaction with 3,3-dimethylacryloyl chloride, cyclization, and oxidation using cerium ammonium nitrate to 4-keto-α-lapachone (2,2-dimethyl-4-keto-1-oxa-1,2,3,4-tetrahydroanthra-5,10-quinone). Reduction by biotransformation using Mortierellaisabellina ATCC 42613 gave (S)-4-hydroxy-α-lapachone in high (> 95%) optical purity. Reduction of several 2,2-dimethyl-4-chromanones to the corresponding (S)-alcohols by M. isabellina is also reported. Keywords: biotransformation, chemoenzymatic, 4-hydroxy-α-lapachone, Mortierellaisabellina.

  1-甲氧基-2-萘酚通过MOM醚形成、C-3处的锂化、与3,3-二甲基丙烯酰氯反应、环化以及使用铈铵硝酸盐氧化转化为4-酮基-α-拉帕醌（2,2-二甲基-4-酮-1-氧杂-1,2,3,4-四氢蒽-5,10-喹啉）。使用MOrtierellaisabellina ATCC 42613的生物转化还原得到高（> 95%）光学纯度的（S）-4-羟基-α-拉帕醌。报道了M. isabellina将几种2,2-二甲基-4-色酮还原为相应的（S）-醇类。关键词：生物转化、化学酶、4-羟基-α-拉帕醌、MOrtierellaisabellina。
• SYNTHESIS OF 2,2-DIMETHYL-3, 4-EPOXY-2<b><i>H</i></b>-NAPHTHO[2,3-<i>b</i>]PYRAN-5, 10-DIONE
  作者：Ricardo A. Tapia、Claudia Lizama、Claudio López、Jaime A. Valderrama

  DOI：10.1081/scc-100000588

  日期：2001.1

  A short and convenient synthesis of benzopyranoquinone 6 and its application to the preparation of epoxynaphthopyanoquinone 1 is described.
• Regioselective Synthesis of the Bridged Tricyclic Core of <i>Garcinia </i>Natural Products via Intramolecular Aryl Acrylate Cycloadditions
  作者：Eric J. Tisdale、Chinmay Chowdhury、Binh G. Vong、Hongmei Li、Emmanuel A. Theodorakis

  DOI：10.1021/ol017278w

  日期：2002.3.1

  [GRAPHICS]Two different routes to the tricyclic core of Garcinia-derived natural products are described. The first approach is based on a tandem Claisen/Diels-Alder rearrangement and delivers the desired lactone 14. The second approach, employing a Wessely oxidation/Diels-Alder protocol, leads to the same caged heterocycle, albeit with modified constitution.