2-amino-5-chloro-[α-¹⁴C]benzophenone | 32464-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-5-chloro-[α-¹⁴C]benzophenone
• 英文别名: (2-amino-5-chlorophenyl)-phenyl(114C)methanone
• CAS: 32464-19-0
• 化学式: C₁₃H₁₀ClNO
• 分子量: 233.671
• InChiKey: ZUWXHHBROGLWNH-ALWQSETLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-5-chloro-[α-¹⁴C]benzophenone 、 甲基溴化镁 以 二丁醚 为溶剂， 反应 2.0h， 以100%的产率得到5-chloro-2-amino-α-methyl-α-phenyl-[α-14C]benzyl alcohol
  参考文献：
  名称：

  Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)

  摘要：

  Carbonation of phenyl lithium with (CO2)-C-14, followed by reduction of [(CO2)-C-14] benzoic acid, led to [alpha-C-14] benzyl alcohol 3, the oxidation of which afforded the [alpha-C-14] benzaldehyde 4. The latter, then condensed with pivoylamide 6 (trimethyl acetamide-N-(2-lithio-4chlorophenyl) gave 5-chloro-2 (t-Butylamide)-alpha-phenyl-[-alpha-C-14] benzyl alcohol 2 which was then oxidized to ketone 8 which it self were subsequently hydrolysed to 5-chloro-2-amino-[-alpha-C-14]benzophenone 9. Grignard reaction of 9 with methylmagnesium iodide gave 5-chloro-2-amino-alpha-methyl-alpha-phenyl-[-alpha-C-14] benzyl alcohol 10. Treatment of the alcohol 10 with ethylthioisocyanate, followed by cyclisation led to 6-chloro-2-(ethylamino)-4-methyl-4-phenyl-[-4-C-14]-benzoxazine 12. The latter was acidified to give rise to Etifoxine hydrochloride 13 in an overall yield of about 31%based on [C-14] barium carbonate.

  DOI：

  10.1002/(sici)1099-1344(199711)39:11<907::aid-jlcr38>3.0.co;2-2
• 作为产物：
  描述：

  N-[2-(benzoyl)-4-chlorophenyl]-2,2-dimethylpropanamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 2-amino-5-chloro-[α-¹⁴C]benzophenone
  参考文献：
  名称：

  Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)

  摘要：

  Carbonation of phenyl lithium with (CO2)-C-14, followed by reduction of [(CO2)-C-14] benzoic acid, led to [alpha-C-14] benzyl alcohol 3, the oxidation of which afforded the [alpha-C-14] benzaldehyde 4. The latter, then condensed with pivoylamide 6 (trimethyl acetamide-N-(2-lithio-4chlorophenyl) gave 5-chloro-2 (t-Butylamide)-alpha-phenyl-[-alpha-C-14] benzyl alcohol 2 which was then oxidized to ketone 8 which it self were subsequently hydrolysed to 5-chloro-2-amino-[-alpha-C-14]benzophenone 9. Grignard reaction of 9 with methylmagnesium iodide gave 5-chloro-2-amino-alpha-methyl-alpha-phenyl-[-alpha-C-14] benzyl alcohol 10. Treatment of the alcohol 10 with ethylthioisocyanate, followed by cyclisation led to 6-chloro-2-(ethylamino)-4-methyl-4-phenyl-[-4-C-14]-benzoxazine 12. The latter was acidified to give rise to Etifoxine hydrochloride 13 in an overall yield of about 31%based on [C-14] barium carbonate.

  DOI：

  10.1002/(sici)1099-1344(199711)39:11<907::aid-jlcr38>3.0.co;2-2

文献信息

• ISHIHAMA HIROSHI; KABUTO SHIGEO; TAMAKI TARO, RADIOISOTOPES, 1978, 27, NO 5, 235-240
  作者：ISHIHAMA HIROSHI、 KABUTO SHIGEO、 TAMAKI TARO

  DOI：——

  日期：——