1-(2,3-二氢苯并[b][1,4]二噁英-6-基)-2-丙酮 | 15033-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 1-(2,3-二氢苯并[b][1,4]二噁英-6-基)-2-丙酮
• 英文名称: 1-(3,4-ethylenedioxyphenyl)propan-2-one
• 英文别名: 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)propan-2-one；1-(2,3-dihydro-1,4-benzodioxin-6-yl)propan-2-one
• CAS: 15033-65-5
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD00210428
• 分子量: 192.214
• InChiKey: BKWCNNIPHHIQBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1-(2,3-二氢苯并[b][1,4]二噁英-6-基)-2-丙酮 在 盐酸 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 68.0h， 生成 (S)-(+)-1-(3,4-ethylenedioxyphenyl)-N-methyl-2-aminopropane hydrochloride
  参考文献：
  名称：

  Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

  摘要：

  N-Methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA; 'Ecstasy'; 1) and its beta-keto analog methylone (MDMC; 2) are popular drugs of abuse. Little is known about their ring-expanded ethylenedioxy homologs. Here, we prepared N-methyl-(3,4-ethylenedioxyphenyl)-2-aminopropane (EDMA; 3), both of its optical isomers, and beta-keto EDMA (i.e., EDMC; 4) to examine their effects at transporters for serotonin (SERT), dopamine (DAT), and norepinephrine (NET). In general, ring-expansion of the methylenedioxy group led to a several-fold reduction in potency at all three transporters. With respect to EDMA (3), S(+)3 was 6-fold, 50-fold, and 8-fold more potent than its R(-) enantiomer at SERT, DAT, and NET, respectively. Overall, in the absence of a beta-carbonyl group, the ethylenedioxy (i.e., 1,4-dioxane) substituent seems better accommodated at SERT than at DAT and NET. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.035
• 作为产物：
  描述：

  3,4-ethylenedioxy-β-methyl-β-nitrostyrene 在 铁粉 、 溶剂黄146 作用下， 反应 3.0h， 以78%的产率得到1-(2,3-二氢苯并[b][1,4]二噁英-6-基)-2-丙酮
  参考文献：
  名称：

  Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

  摘要：

  N-Methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA; 'Ecstasy'; 1) and its beta-keto analog methylone (MDMC; 2) are popular drugs of abuse. Little is known about their ring-expanded ethylenedioxy homologs. Here, we prepared N-methyl-(3,4-ethylenedioxyphenyl)-2-aminopropane (EDMA; 3), both of its optical isomers, and beta-keto EDMA (i.e., EDMC; 4) to examine their effects at transporters for serotonin (SERT), dopamine (DAT), and norepinephrine (NET). In general, ring-expansion of the methylenedioxy group led to a several-fold reduction in potency at all three transporters. With respect to EDMA (3), S(+)3 was 6-fold, 50-fold, and 8-fold more potent than its R(-) enantiomer at SERT, DAT, and NET, respectively. Overall, in the absence of a beta-carbonyl group, the ethylenedioxy (i.e., 1,4-dioxane) substituent seems better accommodated at SERT than at DAT and NET. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.035

文献信息

• Novel compounds
  申请人：——

  公开号：US20040235821A1

  公开（公告）日：2004-11-25

  The invention relates to thiophene carboxamides of formula (I), wherein R 1 , R 2 , R 3 , A, n and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. 1

  该发明涉及式(I)的噻吩羧酰胺，其中R1、R2、R3、A、n和X如规范中所定义，以及用于其制备的过程和中间体，包含它们的制药组合物以及它们在治疗中的使用。1
• Vanilloid Receptor Ligands, Pharmaceutical Compositions Containing Them, Process For Making Them, and Use Thereof to Treat Pain and Other Conditions
  申请人：Frank Robert

  公开号：US20110301156A1

  公开（公告）日：2011-12-08

  Vanilloid receptor ligand compounds corresponding to formula I: pharmaceutical compositions containing such compounds, a process for producing such compounds, and methods of using such compounds for treating or inhibiting pain and various other disorders or conditions.

  Vanilloid受体配体化合物I式对应的药物组成物，含有这种化合物的药物组成物，制备这种化合物的过程，以及使用这种化合物治疗或抑制疼痛和各种其他疾病或情况的方法。
• Shield Machine-like Substrate Walking Strategy-Based Pocket Engineering of F-Amine Dehydrogenase for Accessing Structurally Diverse Fused-Ring and Linked-Ring Aryl Ketones
  作者：Tao Wu、Yan Xu、Yao Nie、Xiaoqing Mu

  DOI：10.1021/acscatal.4c00068

  日期：2024.2.16

  Although amine dehydrogenases (AmDHs) are emerging as attractive biocatalysts for chiral amine synthesis, their synthetic application in structurally diverse arylamines remains challenging, given the limited substrate acceptance. Substrate walking is an effective coevolution strategy to confer targeted substrate acceptance to an enzyme through a stepwise mutagenesis landscape adaptation. Here, based

  尽管胺脱氢酶（AmDH）正在成为手性胺合成的有吸引力的生物催化剂，但由于底物接受度有限，它们在结构多样的芳胺中的合成应用仍然具有挑战性。底物行走是一种有效的共同进化策略，通过逐步诱变景观适应赋予酶目标底物接受能力。在此，基于传统的底物行走策略，我们报告了一种类似盾构机的底物行走策略，以快速从芽孢杆菌中进化出F- Bb AmDH ，以获取难以胺化的稠环和连接环芳基酮。合理选择一组苯环位于侧链末端且碳骨架规则延伸的单环芳基酮同系物作为过渡底物。基于过渡底物的活性和特异性增强，鉴定出具有扩展的目标稠环和连接环芳基酮接受性的优质突变体库，从而能够以高达 94% 的产率和 99 的产率合成药物和生物活性化合物相关的芳胺。 % ee ( R ) 或 99:1顺式/反式。基于结构的计算结果提供了对扩大底物接受度来源的分子见解。我们的工作展示了一种简洁的工程工作流程，用于结构多样的底物面板的酶的集体接受进化，并且在酶工程中具有广阔的前景。
• THIOPHENYL COMPOUNDS AS MEDICAMENTS
  申请人：AstraZeneca AB

  公开号：EP1421079B1

  公开（公告）日：2007-02-07
• NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：SNU R&DB FOUNDATION

  公开号：US20160340331A1

  公开（公告）日：2016-11-24

  A compound inhibiting Hsp90 and a pharmaceutical composition including the same as an active ingredient are described, which compound is represented by formula 2 and suppresses the expression of Hsp90, inhibits the accumulation of HIF-1α, the Hsp90 client protein, and efficiently inhibits the activation of VEGF. The compound displays low cytotoxicity and can be effectively used as an active ingredient of an anti-cancer agent, a diabetic retinopathy treating agent, and an anti-arthritic agent.