5-hydroxy-4,4-dimethylpentyl 2,2-dimethylpropanate | 114273-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-hydroxy-4,4-dimethylpentyl 2,2-dimethylpropanate
• 英文别名: 5-Hydroxy-4,4-dimethylpentyl 2,2-dimethylpropanoate；(5-hydroxy-4,4-dimethylpentyl) 2,2-dimethylpropanoate
• CAS: 114273-70-0
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: UILJQUIMPMSLDX-UHFFFAOYSA-N

物化性质

• 沸点：
  285.0±23.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡喃 、 5-hydroxy-4,4-dimethylpentyl 2,2-dimethylpropanate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到5-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4,4-dimethylpentyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  EXTERNALLY MASKED NEOPENTYL SULFONYL ESTER CYCLIZATION RELEASE PRODRUGS OF ACAMPROSATE, COMPOSITIONS THEREOF, AND METHODS OF USE

  摘要：

  掩蔽的氮取代和氧取代的新戊烷磺酰酯丙戊酸酯前药，包含这种前药的药物组合物，以及使用这种前药和组合物治疗疾病的方法被披露。具体来说，披露了表现出增强口服生物利用度的丙戊酸酯前药和使用丙戊酸酯前药治疗神经退行性疾病、精神疾病、情绪障碍、焦虑障碍、躯体形式障碍、运动障碍、物质滥用障碍、暴饮暴食障碍、皮层扩散性抑郁相关障碍、耳鸣、睡眠障碍、多发性硬化和疼痛的方法。

  公开号：

  US20090082464A1
• 作为产物：
  描述：

  4,4-Dimethylpentyl 2,2-dimethylpropanoate 在 双氧水 、 溶剂黄146 、 C₄₆H₄₀F₁₈MnN₆O₆S₂ 作用下， 以23 %的产率得到5-hydroxy-4,4-dimethylpentyl 2,2-dimethylpropanate
  参考文献：
  名称：

  10.1002/anie.202402858

  摘要：

  AbstractThe tert‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic and organometallic molecules. Because of the combination of a high bond dissociation energy (~100 kcal mol−1) and limited accessibility, in the absence of directing groups, neither radical nor organometallic approaches are effective for the chemical modification of tert‐butyl C−H bonds. Herein we overcome these limits by employing a highly electrophilic manganese catalyst, [Mn(CF3bpeb)(OTf)2], that operates in the strong hydrogen bond donor solvent nonafluoro‐tert‐butyl alcohol (NFTBA) and catalytically activates hydrogen peroxide to generate a powerful manganese‐oxo species that effectively oxidizes tert‐butyl C−H bonds. Leveraging on the interplay of steric, electronic, medium and torsional effects, site‐selective and product chemoselective hydroxylation of the tert‐butyl group is accomplished with broad reaction scope, delivering primary alcohols as largely dominant products in preparative yields. Late‐stage hydroxylation at tert‐butyl sites is demonstrated on 6 densely functionalized molecules of pharmaceutical interest. This work uncovers a novel disconnection approach, harnessing tert‐butyl as a potential functional group in strategic synthetic planning for complex molecular architectures.

  DOI：

  10.1002/anie.202402858

文献信息

• [EN] EXTERNALLY MASKED NEOPENTYL SULFONYL ESTER CYCLIZATION RELEASE PRODRUGS OF ACAMPROSATE, COMPOSITIONS THEREOF, AND METHODS OF USE<br/>[FR] PROMÉDICAMENTS DE LIBÉRATION DE CYCLISATION D'ESTER DE NÉOPENTYLE SULFONYLE D'ESTER D'ACIDE PANTOÏQUE MASQUÉS EXTÉRIEUREMENT, LEURS COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：XENOPORT INC

  公开号：WO2009033079A1

  公开（公告）日：2009-03-12

  Masked nitrogen-substituted and oxygen-substituted neopentyl sulfonyl ester prodrugs of acamprosate of formulae (I) and (III), pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs exhibiting enhanced oral bioavailability and methods of using acamprosate prodrugs to treat neurodegenerative disorders, psychotic disorders, mood disorders, anxiety disorders, somatoform disorders, movement disorders, substance abuse disorders, binge eating disorders, cortical spreading depression related disorders, tinnitus, sleeping disorders, multiple sclerosis and pain are disclosed.
• EXTERNALLY MASKED NEOPENTYL SULFONYL ESTER CYCLIZATION RELEASE PRODRUGS OF ACAMPROSATE, COMPOSITIONS THEREOF, AND METHODS OF USE
  申请人：Jandeleit Bernd

  公开号：US20090082464A1

  公开（公告）日：2009-03-26

  Masked nitrogen-substituted and oxygen-substituted neopentyl sulfonyl ester prodrugs of acamprosate, pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs exhibiting enhanced oral bioavailability and methods of using acamprosate prodrugs to treat neurodegenerative disorders, psychotic disorders, mood disorders, anxiety disorders, somatoform disorders, movement disorders, substance abuse disorders, binge eating disorder, cortical spreading depression related disorders, tinnitus, sleeping disorders, multiple sclerosis, and pain are disclosed.

  掩蔽的氮取代和氧取代的新戊烷磺酰酯丙戊酸酯前药，包含这种前药的药物组合物，以及使用这种前药和组合物治疗疾病的方法被披露。具体来说，披露了表现出增强口服生物利用度的丙戊酸酯前药和使用丙戊酸酯前药治疗神经退行性疾病、精神疾病、情绪障碍、焦虑障碍、躯体形式障碍、运动障碍、物质滥用障碍、暴饮暴食障碍、皮层扩散性抑郁相关障碍、耳鸣、睡眠障碍、多发性硬化和疼痛的方法。
• 10.1002/anie.202402858
  作者：Chan, Siu-Chung、Palone, Andrea、Bietti, Massimo、Costas, Miquel

  DOI：10.1002/anie.202402858

  日期：——

  AbstractThe tert‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic and organometallic molecules. Because of the combination of a high bond dissociation energy (~100 kcal mol−1) and limited accessibility, in the absence of directing groups, neither radical nor organometallic approaches are effective for the chemical modification of tert‐butyl C−H bonds. Herein we overcome these limits by employing a highly electrophilic manganese catalyst, [Mn(CF3bpeb)(OTf)2], that operates in the strong hydrogen bond donor solvent nonafluoro‐tert‐butyl alcohol (NFTBA) and catalytically activates hydrogen peroxide to generate a powerful manganese‐oxo species that effectively oxidizes tert‐butyl C−H bonds. Leveraging on the interplay of steric, electronic, medium and torsional effects, site‐selective and product chemoselective hydroxylation of the tert‐butyl group is accomplished with broad reaction scope, delivering primary alcohols as largely dominant products in preparative yields. Late‐stage hydroxylation at tert‐butyl sites is demonstrated on 6 densely functionalized molecules of pharmaceutical interest. This work uncovers a novel disconnection approach, harnessing tert‐butyl as a potential functional group in strategic synthetic planning for complex molecular architectures.