benzo[d][1,3]dioxole-5-d

• 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: benzo[d][1,3]dioxole-5-d
• 英文别名: 5-Deuterio-1,3-benzodioxole；5-deuterio-1,3-benzodioxole
• 化学式: C₇H₆O₂
• 分子量: 123.115
• InChiKey: FTNJQNQLEGKTGD-MICDWDOJSA-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

• 作为产物：
  描述：

  胡椒环 在 三苯基膦双(三氟甲磺酰亚胺)金 、 重水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以98%的产率得到benzo[d][1,3]dioxole-5-d
  参考文献：
  名称：

  Gold-Catalyzed Proto- and Deuterodeboronation

  摘要：

  A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-sigma-phenyl intermediate.

  DOI：

  10.1021/acs.joc.5b01041

文献信息

• NOVEL BENZO[D][1,3]-DIOXOL DERIVATIVES
  申请人：Tung Roger

  公开号：US20080033011A1

  公开（公告）日：2008-02-07

  The present invention relates to an isotopologue of paroxetine substituted with deuterium at the methylene carbon of the benzodioxol ring. The isotopologues of this invention selective serotonin reuptake inhibitors (SSRIs) and possess unique biopharmaceutical and metabolic properties compared to paroxetine. They may also be used to accurately determine the concentration of paroxetine in biological fluids and to determine metabolic patterns of paroxetine and its isotopologues. The invention further provides compositions comprising these deuterated isotopologues and methods of treating diseases and conditions that are responsive to increased neuronal serotonin transmission, alone and in combination with additional agents.

  本发明涉及一种取代苯并二氧戊环环上亚甲基碳上的氘代帕罗西汀同位素。本发明的同位素是选择性血清素再摄取抑制剂(SSRIs)，与帕罗西汀相比具有独特的生物制药和代谢特性。它们还可以用于准确测定生物液体中帕罗西汀的浓度以及确定帕罗西汀及其同位素的代谢模式。本发明还提供了包含这些氘代同位素的组合物和治疗对增加神经元血清素传递敏感的疾病和状况的方法，单独或与其他药物联合使用。
• Novel benzo[D][1,3]-dioxol derivatives
  申请人：Tung Roger

  公开号：US20070191432A1

  公开（公告）日：2007-08-16

  The present invention relates to an isotopologue of Compound 1 substituted with deuterium at the methylene carbon of the benzodioxol ring. The isotopologues of this invention selective serotonin reuptake inhibitors (SSRIs) and possess unique biopharmaceutical and metabolic properties compared to Compound 1. They may also be used to accurately determine the concentration of Compound 1 in biological fluids and to determine metabolic patterns of Compound 1 and its isotopologues. The invention further provides compositions comprising these deuterated isotopologues and methods of treating diseases and conditions that are responsive to increased neuronal serotonin transmission, alone and in combination with additional agents.

  本发明涉及一种在苯并二氧杂环环的亚甲基碳上取代氘的化合物1的同位素。本发明的同位素是选择性血清素再摄取抑制剂(SSRI)，与化合物1相比具有独特的生物制药和代谢特性。它们还可以用于准确确定生物液中化合物1的浓度，并确定化合物1及其同位素的代谢模式。本发明还提供了包含这些氘同位素的组合物以及治疗对增加神经元血清素传递敏感的疾病和病症的方法，单独或与其他药物联合使用。
• Novel benzo[d][1,3]-dioxol derivatives
  申请人：Tung Roger

  公开号：US20080287495A1

  公开（公告）日：2008-11-20

  The present invention relates to an isotopologue of Compound 1 substituted with deuterium at the methylene carbon of the benzodioxol ring. The isotopologues of this invention selective serotonin reuptake inhibitors (SSRIs) and possess unique biopharmaceutical and metabolic properties compared to Compound 1. They may also be used to accurately determine the concentration of Compound 1 in biological fluids and to determine metabolic patterns of Compound 1 and its isotopologues. The invention further provides compositions comprising these deuterated isotopologues and methods of treating diseases and conditions that are responsive to increased neuronal serotonin transmission, alone and in combination with additional agents.

  本发明涉及一种在苯二氧杂环环的亚甲基碳上用氘取代的化合物1的同位素。本发明的同位素选择性地抑制5-羟色胺再摄取，具有与化合物1相比独特的生物制药和代谢特性。它们还可用于准确测定生物液体中化合物1的浓度，并确定化合物1及其同位素的代谢模式。本发明还提供了包含这些氘同位素的组合物和治疗对增加神经元5-羟色胺传递敏感的疾病和病症的方法，单独或与其他药物联合使用。
• DEUTERATED BENZO[D][1,3]-DIOXOL DERIVATIVES
  申请人：Tung Roger

  公开号：US20100222589A1

  公开（公告）日：2010-09-02

  The present invention relates to an isotopologue of Compound 1 substituted with deuterium at the methylene carbon of the benzodioxol ring. The isotopologues of this invention selective serotonin reuptake inhibitors (SSRIs) and possess unique biopharmaceutical and metabolic properties compared to Compound 1. They may also be used to accurately determine the concentration of Compound 1 in biological fluids and to determine metabolic patterns of Compound 1 and its isotopologues. The invention further provides compositions comprising these deuterated isotopologues and methods of treating diseases and conditions that are responsive to increased neuronal serotonin transmission, alone and in combination with additional agents.

  本发明涉及一种在苯并二氧杂环环的亚甲基碳上用氘取代的化合物1的同位素。本发明的同位素选择性地抑制5-羟色胺再摄取抑制剂（SSRI），并且与化合物1相比具有独特的生物制药和代谢特性。它们还可以用于准确测定生物体液中化合物1的浓度，并确定化合物1及其同位素的代谢模式。本发明还提供了包含这些氘同位素的组合物和治疗对增加神经元5-羟色胺传递敏感的疾病和病症的方法，单独或与其他药物联合使用。
• NOVEL BENZO[d][1,3]-DIOXOL DERIVATIVES
  申请人：Tung Roger D.

  公开号：US20150196544A1

  公开（公告）日：2015-07-16

  The present invention relates to an isotopologue of Compound 1 substituted with deuterium at the methylene carbon of the benzodioxol ring. The isotopologues of this invention selective serotonin reuptake inhibitors (SSRIs) and possess unique biopharmaceutical and metabolic properties compared to Compound 1. They may also be used to accurately determine the concentration of Compound 1 in biological fluids and to determine metabolic patterns of Compound 1 and its isotopologues. The invention further provides compositions comprising these deuterated isotopologues and methods of treating diseases and conditions that are responsive to increased neuronal serotonin transmission, alone and in combination with additional agents.

  本发明涉及化合物1的同位素拓扑异构体，在苯并二氧杂环环的亚甲基碳上用氘取代。本发明的同位素拓扑异构体是选择性血清素再摄取抑制剂（SSRI），与化合物1相比具有独特的生物制药和代谢特性。它们还可以用于准确测定生物流体中化合物1的浓度，并确定化合物1及其同位素拓扑异构体的代谢模式。本发明还提供了包含这些氘化同位素拓扑异构体的组合物及其治疗对增加神经元血清素传递响应的疾病和病状的方法，单独使用或与其他药物联合使用。