3-dimethoxymethyl-4-methyl-4-(2-pyridyl)cyclohex-2-en-1-omebutan-2-one | 245673-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-dimethoxymethyl-4-methyl-4-(2-pyridyl)cyclohex-2-en-1-omebutan-2-one
• 英文别名: 3-(Dimethoxymethyl)-4-methyl-4-pyridin-2-ylcyclohex-2-en-1-one
• CAS: 245673-36-3
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: CMIZIAIEKCSBSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-dimethoxymethyl-4-methyl-4-(2-pyridyl)cyclohex-2-en-1-omebutan-2-one 在 palladium dihydroxide sodium tetrahydroborate 、 甲酸 、 NH₃*THF 、 氢气 、 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正戊烷 为溶剂， 反应 171.0h， 生成 2-(1β-(5β-benzyloxy-2β-methyl-2α-[2-pyridyl])cyclohexyl)ethanol
  参考文献：
  名称：

  First synthesis of (±)-10β-hydroxy-13β-methylcyclohexa[a]quinolizidine. A convenient route to the ABC-part of 8-azasteroids

  摘要：

  The first synthesis of racemic 10 beta-hydroxy-13 beta-methylcyclohexa[a]quinolizidine is reported. Original construction of AC-bicyclic system is achieved by lateral metallation of 2-ethylpyridine followed by a Robinson annelation, with the creation of a quaternary picolinic carbon center. Functionalization of the A-ring and construction of the B-ring by a stereocontrolled reduction of the pyridinium salt and final hydrogenations afford the ABC-part of an 8-azasteroid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00497-4
• 作为产物：
  描述：

  2-乙基吡啶 在 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 3.0h， 生成 3-dimethoxymethyl-4-methyl-4-(2-pyridyl)cyclohex-2-en-1-omebutan-2-one
  参考文献：
  名称：

  First synthesis of (±)-10β-hydroxy-13β-methylcyclohexa[a]quinolizidine. A convenient route to the ABC-part of 8-azasteroids

  摘要：

  The first synthesis of racemic 10 beta-hydroxy-13 beta-methylcyclohexa[a]quinolizidine is reported. Original construction of AC-bicyclic system is achieved by lateral metallation of 2-ethylpyridine followed by a Robinson annelation, with the creation of a quaternary picolinic carbon center. Functionalization of the A-ring and construction of the B-ring by a stereocontrolled reduction of the pyridinium salt and final hydrogenations afford the ABC-part of an 8-azasteroid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00497-4

文献信息

• First synthesis of (±)-10β-hydroxy-13β-methylcyclohexa[a]quinolizidine. A convenient route to the ABC-part of 8-azasteroids
  作者：Sylvain Célanire、Isabelle Salliot-Maire、Pierre Ribéreau、Alain Godard、Guy Quéguiner

  DOI：10.1016/s0040-4020(99)00497-4

  日期：1999.7

  The first synthesis of racemic 10 beta-hydroxy-13 beta-methylcyclohexa[a]quinolizidine is reported. Original construction of AC-bicyclic system is achieved by lateral metallation of 2-ethylpyridine followed by a Robinson annelation, with the creation of a quaternary picolinic carbon center. Functionalization of the A-ring and construction of the B-ring by a stereocontrolled reduction of the pyridinium salt and final hydrogenations afford the ABC-part of an 8-azasteroid. (C) 1999 Elsevier Science Ltd. All rights reserved.