2-(2-phenylpropan-2-yl)benzo[d]isothiazol-3(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(2-phenylpropan-2-yl)benzo[d]isothiazol-3(2H)-one
• 英文别名: 1,1-Dioxo-2-(2-phenylpropan-2-yl)-1,2-benzothiazol-3-one；1,1-dioxo-2-(2-phenylpropan-2-yl)-1,2-benzothiazol-3-one
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: HOJCZSUULNXREG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基-2-丙醇 在 Lindlar's catalyst 重铬酸吡啶 、 sodium azide 、 四甲基乙二胺 、 氢气 、 仲丁基锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 2-(2-phenylpropan-2-yl)benzo[d]isothiazol-3(2H)-one
  参考文献：
  名称：

  Directed Ortho Metalation−Cross Coupling Strategies. N-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins

  摘要：

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).

  DOI：

  10.1021/jo062385v

文献信息

• Inhibitors of Mitochondrial Fission
  申请人：Queen's University at Kingston

  公开号：US20200323829A1

  公开（公告）日：2020-10-15

  Pharmaceutical compositions that include inhibitors of mitochondrial fission are described for the treatment and/or mitigation of cancer, pulmonary arterial hypertension, cardioprotection, stroke, coronary heart disease, neurological disorder, a neurodegenerative disease, Parksinonism, Huntington's Chorea, Alzheimer's disease, diabetic cardiomyopathy, fatty liver diseases, non-alcoholic fatty liver diseases, or alcohol-related liver disease.

  描述了包括线粒体分裂抑制剂的药物组合物，用于治疗和/或缓解癌症、肺动脉高压、心脏保护、中风、冠心病、神经紊乱、神经退行性疾病、帕金森病、亨廷顿舞蹈症、阿尔茨海默病、糖尿病心肌病、脂肪肝病、非酒精性脂肪肝病或与酒精相关的肝病。
• Inhibitors of mitochondrial fission
  申请人：Queen's University at Kingston

  公开号：US11229629B2

  公开（公告）日：2022-01-25

  Pharmaceutical compositions that include inhibitors of mitochondrial fission are described for the treatment and/or mitigation of cancer, pulmonary arterial hypertension, cardioprotection, stroke, coronary heart disease, neurological disorder, a neurodegenerative disease, Parksinonism, Huntington's Chorea, Alzheimer's disease, diabetic cardiomyopathy, fatty liver diseases, non-alcoholic fatty liver diseases, or alcohol-related liver disease.

  包含线粒体裂变抑制剂的药物组合物被描述用于治疗和/或缓解癌症、肺动脉高压、心脏保护、中风、冠心病、神经系统疾病、神经退行性疾病、帕金森病、亨廷顿舞蹈症、阿尔茨海默病、糖尿病心肌病、脂肪肝、非酒精性脂肪肝或酒精相关肝病。
• <i>N</i>-Cumyl Benzamide, Sulfonamide, and Aryl <i>O</i>-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics
  作者：Costa Metallinos、Sven Nerdinger、Victor Snieckus

  DOI：10.1021/ol990846b

  日期：1999.10.1

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.
• Directed <i>Ortho</i> Metalation−Cross Coupling Strategies. <i>N</i>-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins
  作者：Jérôme Blanchet、Todd Macklin、Patrick Ang、Costa Metallinos、Victor Snieckus

  DOI：10.1021/jo062385v

  日期：2007.4.1

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).