1,4-dimethoxy-2-vinyl-naphthalene | 150556-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dimethoxy-2-vinyl-naphthalene
• 英文别名: 1,4-dimethoxy-2-vinylnaphthalene；2-ethenyl-1,4-dimethoxynaphthalene
• CAS: 150556-60-8
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: LGGIYLJEBLYADQ-UHFFFAOYSA-N

物化性质

• 沸点：
  361.6±22.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2-vinyl-naphthalene 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 以95%的产率得到2-(1,2-dihydroxyethyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of Isagarin, a New Type of Tetracyclic Naphthoquinone from Pentas longiflora

  摘要：

  Isagarin (1) was synthesized in four steps from 1,4-dimethoxynaphthaldehyde (4). The key intermediate 2-(1,2-dihydroxyethyl)-1,4-naphthoquinon (3) was found to react with acylated pyridinium ylides to afford, after spontaneous intramolecular condensation, the desired natural product isagarin (1). Depending on the type of acylated pyridinium ylides, different types of new pyranonaphthoquinone derivatives were obtained.

  DOI：

  10.1021/jo9813888
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以77%的产率得到1,4-dimethoxy-2-vinyl-naphthalene
  参考文献：
  名称：

  Synthesis of Isagarin, a New Type of Tetracyclic Naphthoquinone from Pentas longiflora

  摘要：

  Isagarin (1) was synthesized in four steps from 1,4-dimethoxynaphthaldehyde (4). The key intermediate 2-(1,2-dihydroxyethyl)-1,4-naphthoquinon (3) was found to react with acylated pyridinium ylides to afford, after spontaneous intramolecular condensation, the desired natural product isagarin (1). Depending on the type of acylated pyridinium ylides, different types of new pyranonaphthoquinone derivatives were obtained.

  DOI：

  10.1021/jo9813888

文献信息

• Thiazolidine compounds containing a quinone group, their preparation and
  申请人：Sankyo Company, Limited

  公开号：US05338855A1

  公开（公告）日：1994-08-16

  Compounds of formula (I): ##STR1## (wherein: R.sup.1 is alkyl; R.sup.2 and R.sup.3 are each alkyl or alkoxy, or R.sup.2 and R.sup.3 together form an optionally substituted benzene ring and, when R.sup.2 and R.sup.3 together form said benzene ring, R.sup.1 is hydrogen, halogen or alkyl; R.sup.4 and R.sup.5 both represent hydrogen, or together represent a single carbon-carbon bond; W is a single bond or alkylene; and Z is a hydrogen atom or a cation) have valuable therapeutic and prophylactic activities, including anti-diabetic activities.

  式(I)的化合物：##STR1##（其中：R.sup.1是烷基；R.sup.2和R.sup.3分别是烷基或烷氧基，或者R.sup.2和R.sup.3共同形成一个可选择取代的苯环，当R.sup.2和R.sup.3共同形成该苯环时，R.sup.1是氢、卤素或烷基；R.sup.4和R.sup.5均表示氢，或共同表示一个碳-碳键；W是单键或烷基；Z是氢原子或阳离子），具有有价值的治疗和预防活性，包括抗糖尿病活性。
• Studies on synthesis of quinonylidene Hoveyda-type complexes
  作者：Krzysztof Grudzień、Michał Barbasiewicz

  DOI：10.1002/aoc.3294

  日期：2015.5

  In a quest of redox‐switchable metathesis catalysts we attempted synthesis of ruthenium quinonylidene complexes using two synthetic pathways. First, Hoveyda‐type complexes bearing chelating benzylidene and naphthylidene ligands substituted with two alkoxy/hydroxy groups were synthesized and characterized. The catalysts were tested in model ring‐closing metathesis reactions, and displayed interesting

  为了寻求可氧化还原转换的复分解催化剂，我们尝试使用两种合成途径合成钌醌金属亚基配合物。首先，合成并表征了带有被两个烷氧基/羟基取代的螯合亚苄基和亚萘基配体的霍维达型络合物。催化剂在模型闭环复分解反应中进行了测试，并显示出结构与催化活性之间有趣的相关性。不幸的是，将配合物氧化为苯并萘醌和萘醌衍生物的许多尝试均未成功。然而，第二种方法，使用钌前体与乙烯基醌配体的交换反应，得到了一种在1时观察到的瞬态不稳定产物。1 H NMR。实验数据表明，缺电子醌与钌中心的结合会导致内在不稳定的物种，该物种在环境条件下会发生二次反应。版权所有©2015 John Wiley＆Sons，Ltd.
• First enantioselective synthesis of isagarin, a natural product isolated from Pentas longiflora Oliv.
  作者：Jan Jacobs、Sven Claessens、Eva De Mol、Samir El Hady、Cristina Minguillón、Mercedes Álvarez、Norbert De Kimpe

  DOI：10.1016/j.tet.2010.04.105

  日期：2010.7

  For the first time, an enantioselective synthesis of both 1R,4S-isagarin 1a and 1S,4R-isagarin 1b was achieved starting from 1,4-dimethoxy-2-vinylnaphthalene 2. The key steps involve a Sharpless asymmetric dihydroxylation and reaction with an acetonylating pyridinium ylid. The different optical rotations and melting points of the enantiopure 1R,4S-isagarin 1a and 1S,4R-isagarin 1b with respect to the

  第一次，从1，4-二甲氧基-2-乙烯基萘2开始实现1 R，4 S -isagarin 1a和1 S，4 R -isagarin 1b的对映选择性合成。关键步骤涉及Sharpless不对称二羟基化反应，并与乙酰化吡啶鎓碘化物反应。对映体纯1 R，4 S -isagarin 1a和1 S，4 R -isagarin 1b相对于分离的天然产物的不同旋光度和熔点将得到解决。
• Thiazolidine compounds, their preparation and their therapeutic uses
  申请人：Sankyo Company Limited

  公开号：EP0549365B1

  公开（公告）日：1995-08-09
• Thiazolidine compounds containing a quinone group, their preparation and their therapeutic uses
  申请人：Sankyo Company Limited

  公开号：EP0549366B1

  公开（公告）日：1998-04-15