2-ethoxybenzo[d][1,3]dioxole-5-carbaldehyde | 1638296-86-2

• 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: 2-ethoxybenzo[d][1,3]dioxole-5-carbaldehyde
• 英文别名: 2-ethoxy-1,3-benzodioxole-5-carbaldehyde；42Xpf55ctm
• CAS: 1638296-86-2
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: BXPMJVXEFLMHOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethoxybenzo[d][1,3]dioxole-5-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以95%的产率得到3,4-(ethoxymethylenedioxy)benzyl alcohol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Hapten‐Clicked Analogues of The Antigenic Peptide Melan‐A/MART‐1 _26(27L)‐35

  摘要：

  AbstractA click‐chemistry‐based approach was implemented to prepare peptidomimetics designed in silico and made from aromatic azides and a propargylated GIGI‐mimicking platform derived from the altered Melan‐A/MART‐126(27L)‐35 antigenic peptide ELAGIGILTV. The CuI‐catalyzed Huisgen cycloaddition was carried out on solid support to generate rapidly a first series of peptidomimetics, which were evaluated for their capacity to dock at the interface between the major histocompatibility complex class‐I (MHC‐I) human leucocyte antigen (HLA)‐A2 and T‐cell receptors (TCRs). Despite being a weak HLA‐A2 ligand, one of these 11 first synthetic compounds bearing a p‐nitrobenzyl‐triazole side chain was recognized by the receptor proteins of Melan‐A/MART‐1‐specific T‐cells. After modification of the N and C termini of this agonist, which was intended to enhance HLA‐A2 binding, one of the resulting seven additional compounds triggered significant T‐cell responses. Thus, these results highlight the capacity of naturally circulating human TCRs that are specific for the native Melan‐A/MART‐126‐35 peptide to cross‐react with peptidomimetics bearing organic motifs structurally different from the native central amino acids.

  DOI：

  10.1002/cmdc.202000038
• 作为产物：
  描述：

  原甲酸三乙酯 、 3,4-二羟基苯甲醛 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.5h， 以68%的产率得到2-ethoxybenzo[d][1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  2-氨基-4-（2-乙氧基苯并[d] [1,3]二恶酚-5-基）-4H-吡喃-3-碳腈衍生物的合成及其生物学评价

  摘要：

  咪唑在温和的反应条件下开发了一类新的取代的2-氨基-4-（2-乙氧基苯并[d] [1,3]二恶酚-5-基）-4-H-吡喃-3-腈的衍生物。通过该催化方案，以高产率组装了各种功能化的2-氨基-4-（2-乙氧基苯并[d] [1,3]二恶酚-5-基）-4-H-吡喃-3-腈骨架。新合成的化合物已通过IR，1 H NMR，13 C NMR和质谱数据进行了表征。然后评估化合物的抗微生物活性。

  DOI：

  10.1002/jhet.3152

文献信息

• [EN] RESVERATROL ANALOGS AND THERAPEUTIC USES THEREOF<br/>[FR] ANALOGUES DE RESVÉRATROL ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：CT FOR DRUG RES AND DEV

  公开号：WO2014183221A1

  公开（公告）日：2014-11-20

  Resveratrol analogs and their use to inhibit Kv1.5 channels are provided. The resveratrol analogs are useful in the treatment of atrial arrhythmias, including atrial fibrillation (AF). Exemplary resveratrol analogs are compounds of general Formula (I):

  白藜芦醇类似物及其用于抑制Kv1.5通道的方法已提供。这些白藜芦醇类似物在治疗心房心律失常，包括心房颤动（AF）方面很有用。示例白藜芦醇类似物是一般式（I）的化合物：
• [EN] PROCESS FOR THE PREPARATION OF DROXIDOPA<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DROXIDOPA
  申请人：PIRAMAL ENTPR LTD

  公开号：WO2016147133A1

  公开（公告）日：2016-09-22

  The present invention provides a novel process for the preparation of droxidopa, a synthetic amino acid precursor of norepinephrine. The process is a stereoselective process for the preparation of droxidopa using asymmetric induction and thus avoids synthetic process involving chiral resolution. The present invention also provides novel intermediates of formula III, formula V and formula VI.

  本发明提供了一种新的方法，用于制备多巴酚羧酸（droxidopa），一种去甲肾上腺素的合成氨基酸前体。该方法是一种立体选择性方法，用于使用不对称诱导制备多巴酚羧酸，因此避免了涉及手性分离的合成过程。本发明还提供了三个新的中间体，分别为公式III、公式V和公式VI。
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF DROXIDOPA AND ITS INTERMEDIATE<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE DROXIDOPA ET SON INTERMÉDIAIRE
  申请人：PIRAMAL ENTPR LTD

  公开号：WO2017168313A1

  公开（公告）日：2017-10-05

  The present invention provides an improved process for preparation of L-threo-(2S,3R)-3-(3.4- dihydroxyphenyl)serine (I) (Droxidopa) and its salts; comprising (a) reaction of the aldehyde compound (III) (as described herein) with Metal complex (II) (as described herein), and (b) hydrolysis of the compound (IV) obtained from step (a) in presence of acid. The present invention also relates to a novel intermediates metal chiral complex (IV) for the preparation of Droxidopa.

  本发明提供了一种改进的L-threo-(2S,3R)-3-(3.4-二羟基苯基)丝氨酸（I）（Droxidopa）及其盐的制备方法，包括（a）将醛化合物（III）（如本文所述）与金属配合物（II）（如本文所述）反应，以及（b）在酸存在下水解步骤（a）所得化合物（IV）。本发明还涉及一种新的中间体金属手性配合物（IV），用于制备Droxidopa。
• Synthesis of 2-amino-4-(2-ethoxybenzo[d][1,3]dioxol-5-yl)-4<i>H</i>-pyran-3-Carbonitrile Derivatives and Their Biological Evaluation
  作者：Amresh Baitha、Ajay Gopinathan、Kartik Krishnan、Vijay V. Dabholkar

  DOI：10.1002/jhet.3152

  日期：2018.5

  A new class of substituted 2‐amino‐4‐(2‐ethoxybenzo[d][1,3]dioxol‐5‐yl)‐4H‐pyran‐3‐carbonitrile derivatives catalyzed by Imidazole under mild reaction conditions has been developed. A variety of functionalized 2‐amino‐4‐(2‐ethoxybenzo[d][1,3]dioxol‐5‐yl)‐4H‐pyran‐3‐carbonitrile scaffolds were assembled in high yields by this catalytic protocol. The newly synthesized compounds have been characterized

  咪唑在温和的反应条件下开发了一类新的取代的2-氨基-4-（2-乙氧基苯并[d] [1,3]二恶酚-5-基）-4-H-吡喃-3-腈的衍生物。通过该催化方案，以高产率组装了各种功能化的2-氨基-4-（2-乙氧基苯并[d] [1,3]二恶酚-5-基）-4-H-吡喃-3-腈骨架。新合成的化合物已通过IR，1 H NMR，13 C NMR和质谱数据进行了表征。然后评估化合物的抗微生物活性。
• Process for the preparation of droxidopa and its intermediate
  申请人：PIRAMAL PHARMA LIMITED

  公开号：US11192848B2

  公开（公告）日：2021-12-07

  The present invention provides an improved process for preparation of the L-threo-(2S,3R)-3-(3 4-dihydroxyphenyl)serine (I) or a salt thereof, which is known as Droxidopa; comprising (a) recovery of the by-product compound (V) (as described herein) from the crude compound (I), and (b) recycling and re-use it for the preparation of droxidopa. Accordingly, the present invention relates to an improved economical process for the preparation of L-threo-(2S,3R)-3-(3.4-dihydroxyphenyl)serine (I) or its pharmaceutically acceptable salts; wherein the process relates to recovery and recycling of the by-product compound (V) and also to re-use it for the preparation of droxidopa.

  本发明提供了一种制备 L-硫代-(2S,3R)-3-(3.4-二羟基苯基)丝氨酸(I)或其盐(称为屈昔多巴)的改进工艺，包括(a)从粗化合物(I)中回收副产物化合物(V)(如本文所述)，以及(b)回收并再次用于制备屈昔多巴。因此，本发明涉及一种制备 L-苏-(2S,3R)-3-(3.4-二羟基苯基)丝氨酸(I)或其药学上可接受的盐的改进的经济工艺；其中该工艺涉及副产物化合物(V)的回收和循环利用，还涉及将其重新用于制备屈昔多巴。