Dideuterium benzo[d][1,3]dioxol | 14049-42-4

• 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: Dideuterium benzo[d][1,3]dioxol
• 英文别名: 1,2-(Methylene-d2-dioxy)benzene；2,2-dideuterio-1,3-benzodioxole
• CAS: 14049-42-4
• 化学式: C₇H₆O₂
• 分子量: 124.108
• InChiKey: FTNJQNQLEGKTGD-BFWBPSQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 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：

  Dideuterium benzo[d][1,3]dioxol 在 三氧化硫 N,N-二甲基甲酰胺络合物 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 20.83h， 生成 tert-butyl N-[(2S,3R)-3-deuterio-4-[(2,2-dideuterio-1,3-benzodioxol-5-yl)sulfonyl-[1,1,2,3,3,3-hexadeuterio-2-(trideuteriomethyl)propyl]amino]-3-hydroxy-1-(4-phenylmethoxyphenyl)butan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs

  摘要：

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.001
• 作为产物：
  描述：

  邻苯二酚 在 重水 作用下， 以 二氯甲烷-D2 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Dideuterium benzo[d][1,3]dioxol
  参考文献：
  名称：

  [EN] ISOTOPOLOGES, SALTS, CRYSTALLINE FORMS, STEREOISOMERS, OF METHYLONE AND ETHYLONE AND METHODS OF USE THEREOF
  [FR] ISOTOPOLOGUES, SELS, FORMES CRISTALLINES, STÉRÉOISOMÈRES, DE MÉTHYLONE ET D'ÉTHYLONE ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  Described herein are isotopically enriched analogs of methylone (e.g., deuterated analogs of methylone (e.g., (S)-methylone and (R)-methylone) with improved characteristics. Also described herein are salts (such as hydrochloride salt) and solid forms (e.g., crystalline forms) of methylone. Also described herein are stereoisomers (e.g., enantiomers) of methylone. The present disclosure also provides methods of making and methods of use of the methylone or methylone analogs and solid forms of 3,4-methylenedioxy-N-ethylcathinone hydrochloride described herein to treat brain and neurological disorders such as depression.

  公开号：

  WO2023081403A1
• 作为试剂：
  描述：

  1-氯-4-[1-(4-氯苯基)乙烯基]苯 在 indium(III) bromide 、 Dideuterium benzo[d][1,3]dioxol 、 水 作用下， 以80%的产率得到4,4′-(ethane-1,1-diyl-1-d)bis(chlorobenzene)
  参考文献：
  名称：

  烯烃中的催化转移氢化和区域选择性氢-氘加成

  摘要：

  为芳香族和脂肪族 1,1-二-和三取代烯烃的氢化开发了一种独特且有价值的方法。在催化 InBr 3的存在下，容易获得的 1,3-苯并二氧杂环戊烷和存在于反应混合物中的残留 H 2 O 被用作氢气替代物，并证明是通过改变两侧的烯烃结合氘的实用来源起始氘代 1,3-苯并二恶唑或 D 2 O的来源。实验研究表明，氢化物从 1,3-苯并二恶唑转移到由 H 2 O–InBr 3加合物使烯烃质子化产生的碳阳离子中间体仍然是关键步骤。

  DOI：

  10.1021/acs.joc.3c00272

文献信息

• Synthesis of deuterated catechols and benzo[D][1,3]dioxoles and derivatives thereof
  申请人：Jones Andrew D.

  公开号：US20090143432A1

  公开（公告）日：2009-06-04

  The present invention provides a convenient and efficient process for the synthesis of d 2 -benzo[d][1,3]dioxoles.
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010135424A1

  公开（公告）日：2010-11-25

  The present invention relates to highly functionalized 1,3-diamino-propan-2-ols and pharmaceutically acceptable salts thereof. More specifically, the invention relates to highly functionalized 1,3-diamino-propan-2-ols that are derivatives of the HIV protease inhibitors brecanavir.
• Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs
  作者：Emile J. Velthuisen、Todd M. Baughman、Brian A. Johns、David P. Temelkoff、Jason G. Weatherhead

  DOI：10.1016/j.ejmech.2013.02.001

  日期：2013.5

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.
• [EN] ISOTOPOLOGES, SALTS, CRYSTALLINE FORMS, STEREOISOMERS, OF METHYLONE AND ETHYLONE AND METHODS OF USE THEREOF<br/>[FR] ISOTOPOLOGUES, SELS, FORMES CRISTALLINES, STÉRÉOISOMÈRES, DE MÉTHYLONE ET D'ÉTHYLONE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：[en]TERRAN BIOSCIENCES INC.

  公开号：WO2023081403A1

  公开（公告）日：2023-05-11

  Described herein are isotopically enriched analogs of methylone (e.g., deuterated analogs of methylone (e.g., (S)-methylone and (R)-methylone) with improved characteristics. Also described herein are salts (such as hydrochloride salt) and solid forms (e.g., crystalline forms) of methylone. Also described herein are stereoisomers (e.g., enantiomers) of methylone. The present disclosure also provides methods of making and methods of use of the methylone or methylone analogs and solid forms of 3,4-methylenedioxy-N-ethylcathinone hydrochloride described herein to treat brain and neurological disorders such as depression.