5-chloro-2-(β-ethylthiourido)-α-methyl-α-phenyl-[α-14C]benzyl alcohol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-2-(β-ethylthiourido)-α-methyl-α-phenyl-[α-14C]benzyl alcohol
• 英文别名: 1-[4-chloro-2-(1-hydroxy-1-phenyl(114C)ethyl)phenyl]-3-ethylthiourea
• 化学式: C₁₇H₁₉ClN₂OS
• 分子量: 336.859
• InChiKey: PSQXUHVOOSIWTL-GZXVCZRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(β-ethylthiourido)-α-methyl-α-phenyl-[α-14C]benzyl alcohol 在 lead(II) oxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到6-chloro-2-ethylamino-4-methyl-4-phenyl-[4-14C]-4H-3.1 benzoxazine
  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：

  异硫氰酸乙酯 、 5-chloro-2-amino-α-methyl-α-phenyl-[α-14C]benzyl alcohol 以 甲苯 、 Petroleum ether 为溶剂， 反应 5.0h， 以90%的产率得到5-chloro-2-(β-ethylthiourido)-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

文献信息

• Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)
  作者：Elmostafa Azim、Jean Michel Dupuy、Françis Lepage、Annie Veyre、Jean Claude Madelmont

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

  日期：1997.11

  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.