5-(2-methoxyvinyl)benzo[d][1,3]dioxole | 906514-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(2-methoxyvinyl)benzo[d][1,3]dioxole
• 英文别名: 5-(2-Methoxyethenyl)-1,3-benzodioxole
• CAS: 906514-12-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: CYLPXUHJWJWYJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  285.0±9.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-methoxyvinyl)benzo[d][1,3]dioxole 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以40%的产率得到胡椒基甲醛
  参考文献：
  名称：

  催化不对称 Pictet-Spengler 平台作为天然生物碱的仿生多样化策略

  摘要：

  四氢异喹啉 (THIQ) 生物碱是一大类生物活性天然产物，其母体化合物和相关的下游生物合成次级代谢物跨越数千个孤立的结构。针对相关 THIQ 的化学酶合成方法依赖于 Pictet-Spenglerase，例如去甲克劳林合成酶 (NCS)，其范围严格限于与多巴胺相关的酚类底物。为了克服化学合成背景下的这些限制，我们在此报告了N的不对称 Pictet-Spengler 反应-氨基甲酰基-β-芳基乙胺与不同的醛对对映体富集的 THIQ。所得产物证明是合成THIQ、阿吗啡、四氢小檗碱、吗啡喃和雄仙碱天然产物的有效中间体。关于阳离子中间体稳定化的新型催化剂设计对于实现高反应性至关重要，同时实现生物相关底物反应的前所未有的立体选择性。

  DOI：

  10.1021/jacs.2c06664
• 作为产物：
  描述：

  胡椒醛 、 甲氧基甲基三苯基氯化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以83%的产率得到5-(2-methoxyvinyl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  高价碘（III）介导的炔丙基胍的级联环化和Kealiinine B和C的总合成

  摘要：

  开发了双乙酸苯基碘鎓（PIDA）促进的炔丙基胍的氧化级联环化。该方案为合成生物碱类kealiinines B和C以及同系物提供了一条有效途径。乙炔取代基的电子性质的差异导致两种环化方式。根据实验结果提出了一种合理的机制。

  DOI：

  10.1002/chem.201700934

文献信息

• Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues
  作者：Denis S. Ermolat'ev、Jitender B. Bariwal、Hans P. L. Steenackers、Sigrid C. J. De Keersmaecker、Erik V. Van der Eycken

  DOI：10.1002/anie.201004256

  日期：2010.12.3

  Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)‐catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds

  纳胺家族的生物碱仅需两个步骤就可以由多种炔丙基胺合成（参见方案：R 1 = Me，R 2 =取代的苄基，R 3 = Ar）。因此，除了在炔丙基胺中原位生成的碳二亚胺之外，银（I）催化的分子内加氢酰胺化作用以及随后的脱保护作用也使人们可以接近许多天然产物和生物活性化合物的杂环核。Boc =叔丁氧羰基，Cbz =碳苄氧基。
• Structural elucidation, bio-inspired synthesis, and biological activities of cyclic diarylpropanes from Horsfieldia kingii
  作者：Rui Zhan、Dashan Li、Yuan-Lie Liu、Xiao-Yan Xie、Lei Chen、Li-Dong Shao、Wen-Jing Wang、Ye-Gao Chen

  DOI：10.1016/j.tet.2020.131494

  日期：2020.10

  Bioactivity-guided phytochemical investigation on 70% aqueous acetone extracts of the twigs and leaves of Horsfieldia kingii led to the isolation of two novel cyclic diarylpropanes (1 and 2) bearing a 2,3-dihydro-1H-indene core, one new diarylpropane (3), six known diarylpropanes (4-9), one flavanol (10), and seven lignans (11-17). Their structures were determined by extensive spectroscopic analysis, electronic circular dichroism calculations, and X-ray diffraction crystallography. Moreover, a biomimetic synthesis of 1 and 2 were accomplished in four steps. The in vitro nitric oxide production inhibition tests of these compounds revealed that compounds (+/-)-2, (+)-2, (-)-2, and 10 were potential with IC50 values lower than 10 AM. Compound 2 could inhibit iNOS expression in LPS-induced RAW264.7 cells at a series of non-cytotoxic concentrations (<20 mu M). Furthermore, the bioassay results also suggested the primary SARs of 1-phenyl-2,3-dihydro-1H-indene based scaffold. (C) 2020 Elsevier Ltd. All rights reserved.
• Strategies for the construction of morphinan alkaloid AB-rings: regioselective Friedel-Crafts-type cyclisations of γ-aryl-β-benzoylamido acids with asymmetrically substituted γ-aryl rings
  作者：Stephen G. Davies、Euan C. Goddard、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson、Jonathan M. Withey

  DOI：10.1016/j.tetasy.2016.02.010

  日期：2016.4

  The regioselectivity of the Friedel-Crafts-type cyclisation of a range of gamma-aryl-B-benzoylamido acids, bearing oxy substituents at the C(3)- and C(4)-positions of the gamma-aryl ring, has been investigated. In all of the cases examined (with 3,4-dimethoxy, 3,4-methylenedioxy and 3-hydroxy-4-methoxy substituents) the Lewis acid promoted cyclisation proceeds with exclusive regioselectivity for attack at the C(6)-position rather than at the C(2)-position, and furnishes the corresponding N- and O-protected 3-amino-6,7-dihydroxy-1-tetralone derivatives. This inherent regioselectivity can be overturned by the regioselective introduction of chlorine as a blocking group for the C(6)-position; subsequent Lewis acid promoted cyclisation then proceeds with exclusive regioselectivity for attack at the C(2)-position to deliver the corresponding N- and O-protected 3-amino-5-chloro-7,8-dihydroxy-1-tetralone derivative. These complementary cyclisation protocols represent useful methods for the preparation of these benzo-fused carbocyclic ring systems, which are the functionalised AB-rings of a range of morphinan alkaloids. (C) 2016 Published by Elsevier Ltd.
• [EN] PROCESSES FOR THE PREPARATION OF THE ENANTIOMERS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE (MDMA) AND N-METHYL-1,3-BENZODIOXOLYLBUTANAMINE (MBDB)<br/>[FR] PROCÉDÉS DE PRÉPARATION DES ÉNANTIOMÈRES DE LA 3,4-MÉTHYLÈNEDIOXYMÉTHAMPHÉTAMINE (MDMA) ET DE LA N-MÉTHYL-1,3-BENZODIOXOLYLBUTANAMINE (MBDB)
  申请人：[en]PHARMALA BIOTECH INC.

  公开号：WO2022232949A1

  公开（公告）日：2022-11-10

  The present application includes a process for preparing the (R)- or (S)- enantiomers of 3,4-methylenedioxymethamphetamine ((R)-MDMA or (S)-MDMA) and (R)- or (S)-N-methyl-1,3-benzodioxolylbutanamine ((R)-MBDB or (S)-MBDB) using (R)- tert-butanesulfinamide or (S)-tert-butanesulfinamideas a chiral auxiliary. (I) The present application also includes novel intermediate compounds useful in the preparation of (R/S)-MDMA and (R/S)-MBDB.
• Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C
  作者：Guilong Tian、Pavel Fedoseev、Erik V. Van der Eycken

  DOI：10.1002/chem.201700934

  日期：2017.4.19

  An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental

  开发了双乙酸苯基碘鎓（PIDA）促进的炔丙基胍的氧化级联环化。该方案为合成生物碱类kealiinines B和C以及同系物提供了一条有效途径。乙炔取代基的电子性质的差异导致两种环化方式。根据实验结果提出了一种合理的机制。