(RS)-5-tert-butyl-4-chloro[3H]methyl-3-methoxyisoxazole | 252354-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-5-tert-butyl-4-chloro[3H]methyl-3-methoxyisoxazole
• 英文别名: 5-Tert-butyl-4-[chloro(tritio)methyl]-3-methoxy-1,2-oxazole
• CAS: 252354-22-6
• 化学式: C₉H₁₄ClNO₂
• 分子量: 205.661
• InChiKey: YTBPEUXDPQWLOO-XHHURNKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-5-tert-butyl-4-chloro[3H]methyl-3-methoxyisoxazole 在 氢溴酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 rac-2-amino-3-(5-tert-butyl-3-hydroxyisoxazolyl)-[3-3H]propionic acid
  参考文献：
  名称：

  Synthesis of deuterium and tritium labelled ( RS )‐2‐amino‐3‐(5‐ tert ‐butyl‐3‐hydroxy‐4‐isoxazolyl)‐propionic acid (ATPA), a selective kainic acid receptor agonist

  摘要：

  (RS)-2-Amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA) is an excitatory amino acid receptor agonist showing selectivity for the kainic acid receptor subtype GluR5. As part of the pharmacological characterization of GluR5 receptors, we now report the synthesis of [H-3]ATPA based on a four-step synthesis using 5-tert-butyl-3-methoxy-4-isoxazolylcarbaldehyde as the starting material. Using this synthetic procedure deuterium and tritium labelled ATPA have been prepared. [H-3]ATPA, with a specific activity of 17 Ci/mmol, was obtained with a radiochemical purity of 98.9%. Attempts to demonstrate specific binding of [H-3]ATPA under conventional rat brain membrane receptor binding conditions were unsuccessful.

  DOI：

  10.1002/(sici)1099-1344(199910)42:10<937::aid-jlcr252>3.0.co;2-#
• 作为产物：
  描述：

  5-tert-butyl-3-methoxyisoxazole-4-carbaldehyde 在 氯化亚砜 、 sodium borotritide 作用下， 以 异丙醇 为溶剂， 反应 2.5h， 生成 (RS)-5-tert-butyl-4-chloro[3H]methyl-3-methoxyisoxazole
  参考文献：
  名称：

  Synthesis of deuterium and tritium labelled ( RS )‐2‐amino‐3‐(5‐ tert ‐butyl‐3‐hydroxy‐4‐isoxazolyl)‐propionic acid (ATPA), a selective kainic acid receptor agonist

  摘要：

  (RS)-2-Amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA) is an excitatory amino acid receptor agonist showing selectivity for the kainic acid receptor subtype GluR5. As part of the pharmacological characterization of GluR5 receptors, we now report the synthesis of [H-3]ATPA based on a four-step synthesis using 5-tert-butyl-3-methoxy-4-isoxazolylcarbaldehyde as the starting material. Using this synthetic procedure deuterium and tritium labelled ATPA have been prepared. [H-3]ATPA, with a specific activity of 17 Ci/mmol, was obtained with a radiochemical purity of 98.9%. Attempts to demonstrate specific binding of [H-3]ATPA under conventional rat brain membrane receptor binding conditions were unsuccessful.

  DOI：

  10.1002/(sici)1099-1344(199910)42:10<937::aid-jlcr252>3.0.co;2-#

文献信息

• Synthesis of deuterium and tritium labelled ( <i>RS</i> )‐2‐amino‐3‐(5‐ <i>tert</i> ‐butyl‐3‐hydroxy‐4‐isoxazolyl)‐propionic acid (ATPA), a selective kainic acid receptor agonist
  作者：Tommy N. Johansen、Calvin R. Hawes、Gareth J. Ellis、Bjarke Ebert、Tine B. Stensbøl、Dorthe da Graça Thrige、Povl Krogsgaard‐Larsen

  DOI：10.1002/(sici)1099-1344(199910)42:10<937::aid-jlcr252>3.0.co;2-#

  日期：1999.10

  (RS)-2-Amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA) is an excitatory amino acid receptor agonist showing selectivity for the kainic acid receptor subtype GluR5. As part of the pharmacological characterization of GluR5 receptors, we now report the synthesis of [H-3]ATPA based on a four-step synthesis using 5-tert-butyl-3-methoxy-4-isoxazolylcarbaldehyde as the starting material. Using this synthetic procedure deuterium and tritium labelled ATPA have been prepared. [H-3]ATPA, with a specific activity of 17 Ci/mmol, was obtained with a radiochemical purity of 98.9%. Attempts to demonstrate specific binding of [H-3]ATPA under conventional rat brain membrane receptor binding conditions were unsuccessful.