6'-tert-butyl-8'-iodo-4'H-spiro[adamantane-2,2'-benzo[e][1,3]oxazine] | 61615-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6'-tert-butyl-8'-iodo-4'H-spiro[adamantane-2,2'-benzo[e][1,3]oxazine]
• 英文别名: 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.13,7)decane]；6-tert-butyl-8-iodospiro[3,4-dihydro-1,3-benzoxazine-2,2'-adamantane]
• CAS: 61615-88-1
• 化学式: C₂₁H₂₈INO
• 分子量: 437.364
• InChiKey: SJXDSEYOLSBXGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6'-tert-butyl-8'-iodo-4'H-spiro[adamantane-2,2'-benzo[e][1,3]oxazine] 、 碘甲烷 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以55%的产率得到6-(1,1-dimethylethyl)-3,4-dihydro-8-iodo-3-methylspiro<2H-1,3-benzoxazinium-2,2'-tricyclo<3.3.1.1^3,7>decane>
  参考文献：
  名称：

  2-(Aminomethyl)phenols, a new class of saluretic agents. 6. Effects of N,O-spiroannulation and subsequent quarternization

  摘要：

  The synthesis of a number of 3,4-dihydrospiro-2H-1,3-benzoxazines and their corresponding benzoxazinium salts are reported. The saluretic effects displayed by these N,O-spiroannulated 2-(aminomethyl)phenols appear to be, in part, inversely related to their respective in vivo rates of hydrolysis. Good antihypertensive effects are found only in spirobenzoxazinium 22. Thus, a combination of spiroannulation and quaternization on 2 to produce 22 leads to a loss of saluretic effects with maintenance of antihypertensive effects and, thereby, serves to separate these pharmacological properties.

  DOI：

  10.1021/jm00358a024
• 作为产物：
  描述：

  金刚烷酮 、 2-氨基甲基-4-叔丁基-6-碘苯酚 在 溶剂黄146 作用下， 以 苯 为溶剂， 反应 4.0h， 以89%的产率得到6'-tert-butyl-8'-iodo-4'H-spiro[adamantane-2,2'-benzo[e][1,3]oxazine]
  参考文献：
  名称：

  2-(Aminomethyl)phenols, a new class of saluretic agents. 6. Effects of N,O-spiroannulation and subsequent quarternization

  摘要：

  The synthesis of a number of 3,4-dihydrospiro-2H-1,3-benzoxazines and their corresponding benzoxazinium salts are reported. The saluretic effects displayed by these N,O-spiroannulated 2-(aminomethyl)phenols appear to be, in part, inversely related to their respective in vivo rates of hydrolysis. Good antihypertensive effects are found only in spirobenzoxazinium 22. Thus, a combination of spiroannulation and quaternization on 2 to produce 22 leads to a loss of saluretic effects with maintenance of antihypertensive effects and, thereby, serves to separate these pharmacological properties.

  DOI：

  10.1021/jm00358a024

文献信息

• 3,4-Dihydrospiro-2H-1,3-benzoxazines and their use in treating edema,
  申请人：Merck & Co., Inc.

  公开号：US04092414A1

  公开（公告）日：1978-05-30

  3,4-Dihydrospiro-2H-1,3-benzoxazines are prepared by condensing aminomethylphenols with cyclic ketones. The products are diuretic and anti-inflammatory agents, and are useful in the treatment of autoimmune diseases, such as multiple sclerosis.

  3,4-二氢螺-2H-1,3-苯并噁嗪是通过将氨甲基酚与环状酮缩合制备而成。该产品具有利尿和抗炎作用，并可用于治疗自身免疫性疾病，如多发性硬化症。
• STOKKER, G. E.;SCHULTZ, E. M.;SMITH, R. L.;CRAGOE, E. J. ,, JR;RUSSO, H. +, J. MED. CHEM., 1983, 26, N 4, 585-590
  作者：STOKKER, G. E.、SCHULTZ, E. M.、SMITH, R. L.、CRAGOE, E. J. ,, JR、RUSSO, H. +

  DOI：——

  日期：——
• 2-(Aminomethyl)phenols, a new class of saluretic agents. 6. Effects of N,O-spiroannulation and subsequent quarternization
  作者：G. E. Stokker、E. M. Schultz、R. L. Smith、E. J. Cragoe、H. F. Russo、L. S. Watson、C. T. Ludden、C. S. Sweet

  DOI：10.1021/jm00358a024

  日期：1983.4

  The synthesis of a number of 3,4-dihydrospiro-2H-1,3-benzoxazines and their corresponding benzoxazinium salts are reported. The saluretic effects displayed by these N,O-spiroannulated 2-(aminomethyl)phenols appear to be, in part, inversely related to their respective in vivo rates of hydrolysis. Good antihypertensive effects are found only in spirobenzoxazinium 22. Thus, a combination of spiroannulation and quaternization on 2 to produce 22 leads to a loss of saluretic effects with maintenance of antihypertensive effects and, thereby, serves to separate these pharmacological properties.