1-N-(3-fluoroadamantyl) isocyanate | 126525-49-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-N-(3-fluoroadamantyl) isocyanate
• 英文别名: (3-fluoroadamantan-1-yl)isocyanate；3-fluoro-1-isocyanatoadamantane；1-Fluoro-3-isocyanatoadamantane
• CAS: 126525-49-3
• 化学式: C₁₁H₁₄FNO
• 分子量: 195.237
• InChiKey: QDOCIUUYMKVAMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-N-(3-fluoroadamantyl) isocyanate 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到1,3-bis(3-fluoroadamantan-1-yl)urea
  参考文献：
  名称：

  Synthesis and properties of 1-(3-fluoroadamantan-1-yl)-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis[3-(3-fluoroadamantan-1-yl)ureas], promising inhibitors of epoxide hydrolase sEH

  摘要：

  通过3-羟基金刚烷-1-羧酸与石川试剂的反应，以及随后与二苯基磷酰叠氮的反应，开发出一种三阶段方法，以76%的产率制备3-氟-1-异氰酸金刚烷。3-氟-1-异氰酸金刚烷与多种脂肪族二胺、含氟苯胺和反式-4-氨基（环己氧基）苯甲酸的反应，可得到一系列

  DOI：

  10.1007/s11172-022-3620-1
• 作为产物：
  描述：

  1-N-(3-fluoroadamantyl) urea 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以73%的产率得到1-N-(3-fluoroadamantyl) isocyanate
  参考文献：
  名称：

  Anderson, Gloria L.; Randolph, Betty J.; Harruna, Issifu I., Synthetic Communications, 1989, vol. 19, # 11-12, p. 1955 - 1964

  摘要：

  DOI：

文献信息

• 1-(1-Acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea (AR9281) as a potent, selective, and orally available soluble epoxide hydrolase inhibitor with efficacy in rodent models of hypertension and dysglycemia
  作者：Sampath-Kumar Anandan、Heather Kay Webb、Dawn Chen、Yi-Xin (Jim) Wang、Basker R. Aavula、Sylvaine Cases、Ying Cheng、Zung N. Do、Upasana Mehra、Vinh Tran、Jon Vincelette、Joanna Waszczuk、Kathy White、Kenneth R. Wong、Le-Ning Zhang、Paul D. Jones、Bruce D. Hammock、Dinesh V. Patel、Randall Whitcomb、D. Euan MacIntyre、James Sabry、Richard Gless

  DOI：10.1016/j.bmcl.2010.12.042

  日期：2011.2

  1-(1-Acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea 14a (AR9281), a potent and selective soluble epoxide hydrolase inhibitor, was recently tested in a phase 2a clinical setting for its effectiveness in reducing blood pressure and improving insulin resistance in pre-diabetic patients. In a mouse model of diet induced obesity, AR9281 attenuated the enhanced glucose excursion following an intraperitoneal glucose tolerance test. AR9281 also attenuated the increase in blood pressure in angiotensin-II-induced hypertension in rats. These effects were dose-dependent and well correlated with inhibition of the sEH activity in whole blood, consistent with a role of sEH in the observed pharmacology in rodents. (C) 2010 Elsevier Ltd. All rights reserved.
• ANDERSON, GLORIA L.;RANDOLPH, BETTY J., SYNTH. COMMUN., 19,(1989) N1-12, C. 1955-1963
  作者：ANDERSON, GLORIA L.、RANDOLPH, BETTY J.

  DOI：——

  日期：——
• Anderson, Gloria L.; Randolph, Betty J.; Harruna, Issifu I., Synthetic Communications, 1989, vol. 19, # 11-12, p. 1955 - 1964
  作者：Anderson, Gloria L.、Randolph, Betty J.、Harruna, Issifu I.

  DOI：——

  日期：——
• Synthesis and properties of 1-(3-fluoroadamantan-1-yl)-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis[3-(3-fluoroadamantan-1-yl)ureas], promising inhibitors of epoxide hydrolase sEH
  作者：B. P. Gladkikh、D. V. Danilov、V. S. D’yachenko、V. V. Burmistrov、G. M. Butov、I. A. Novakov

  DOI：10.1007/s11172-022-3620-1

  日期：2022.9

  A three-stage method for the preparation of 3-fluoro-1-isocyanatoadamantane in 76% yield was developed using the reaction of 3-hydroxyadamantane-1-carboxylic acid with Ishikawa’s reagent and subsequent reaction with diphenylphosphoryl azide. The reaction of 3-fluoro-1-isocyanatoadamantane with a number of aliphatic diamines, fluorine-containing anilines, and trans-4-amino(cyclohexyloxy)benzoic acid afforded a new series of targeted inhibitors of epoxide hydrolase sEH in 43–89% yields. The absence of a methylene bridge between the adamantane and urea moieties led to an increase in the melting points of the synthesized compounds, while the introduction of a fluorine atom reduces their melting points compared to nonfluorinated analogs.

  通过3-羟基金刚烷-1-羧酸与石川试剂的反应，以及随后与二苯基磷酰叠氮的反应，开发出一种三阶段方法，以76%的产率制备3-氟-1-异氰酸金刚烷。3-氟-1-异氰酸金刚烷与多种脂肪族二胺、含氟苯胺和反式-4-氨基（环己氧基）苯甲酸的反应，可得到一系列