3-isoxazolecarboxylic acid 5-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-ethyl ester | 213383-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isoxazolecarboxylic acid 5-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-ethyl ester
• 英文别名: Ethyl 4-[1-(1,3-dioxolanyl)-ethyl]-5-methyl-isoxazole-3-carboxylate；Ethyl 5-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-1,2-oxazole-3-carboxylate
• CAS: 213383-62-1
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: OWIKSAWPBZRYGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-isoxazolecarboxylic acid 5-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-ethyl ester 在 samarium(III) chloride 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.25h， 生成 3-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-1,2-oxazole
  参考文献：
  名称：

  An improved procedure for the lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate

  摘要：

  Ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate was smoothly lithiated at the 5-methyl position, when the 4-acetyl group was protected with a 5,5-dimethyl-1,3-dioxanyl group. The lithio anion was quenched with a variety of electrophiles such as alkyl halides, aldehydes, TMSCl, and Me3SnCl in good to excellent yields. The lithiation of the unprotected compound and the 4-acetyl group protected as 1,3-dioxolanyl both failed. The effects of different bases have been investigated and the addition of LiCl significantly increased yields. Based on variable temperature NMR studies the 5,5-dimethyl-1,3-dioxanyl group appears to occupy a single chair conformation which may facilitate lateral metalation. This represents a facile entry into 5-functionalized 3-isoxazolyl carboxylic acid derivatives as prodrugs for the AMPA glutamate neurotransmitters of the central nervous system. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00781-5
• 作为产物：
  描述：

  3-isoxazolecarboxylic acid 5-methyl-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester 在 对甲苯磺酸 作用下， 以 丙酮 、 苯 为溶剂， 生成 3-isoxazolecarboxylic acid 5-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-ethyl ester
  参考文献：
  名称：

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

  摘要：

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt-Kindler reaction into the corresponding homologated methyl esters after deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01782-1

文献信息

• Lanthanide Catalyzed Synthesis of β-Hydroxyl Amides
  作者：P. Zhou、N. R. Natale

  DOI：10.1080/00397919808004440

  日期：1998.9

  Abstract Lanthanide (III) chloride improved the reaction of carboxylic esters with β-amino alkoxides (generated in situ from β-amino alcohols) and produced β-hydroxyl amides under mild conditions, and in high yields.

  摘要 镧系元素 (III) 氯化物改进了羧酸酯与 β-氨基醇盐（由 β-氨基醇原位生成）的反应，并在温和的条件下以高产率制备了 β-羟基酰胺。
• Inhibitors of Histone Deacetylase
  申请人：Delorme Daniel

  公开号：US20070213330A1

  公开（公告）日：2007-09-13

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶的技术。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了治疗细胞增殖性疾病和病况的组合物和方法。
• US7253204B2
  申请人：——

  公开号：US7253204B2

  公开（公告）日：2007-08-07
• US8088805B2
  申请人：——

  公开号：US8088805B2

  公开（公告）日：2012-01-03
• An improved procedure for the lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate
  作者：David J Burkhart、Peiwen Zhou、Alex Blumenfeld、Brendan Twamley、Nicholas R Natale

  DOI：10.1016/s0040-4020(01)00781-5

  日期：2001.9

  Ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate was smoothly lithiated at the 5-methyl position, when the 4-acetyl group was protected with a 5,5-dimethyl-1,3-dioxanyl group. The lithio anion was quenched with a variety of electrophiles such as alkyl halides, aldehydes, TMSCl, and Me3SnCl in good to excellent yields. The lithiation of the unprotected compound and the 4-acetyl group protected as 1,3-dioxolanyl both failed. The effects of different bases have been investigated and the addition of LiCl significantly increased yields. Based on variable temperature NMR studies the 5,5-dimethyl-1,3-dioxanyl group appears to occupy a single chair conformation which may facilitate lateral metalation. This represents a facile entry into 5-functionalized 3-isoxazolyl carboxylic acid derivatives as prodrugs for the AMPA glutamate neurotransmitters of the central nervous system. (C) 2001 Elsevier Science Ltd. All rights reserved.