tert-butyl 3-(3-chloro-4-cyanophenoxy)cyclobutanecarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl 3-(3-chloro-4-cyanophenoxy)cyclobutanecarboxylate
• 英文别名: (1R,3R)-tert-Butyl 3-(3-chloro-4-cyanophenoxy)cyclobutanecarboxylate；3-(3-Chloro-4-cyano-phenoxy)-cyclobutanecarboxylic acid tert-butyl ester；tert-butyl 3-(3-chloro-4-cyanophenoxy)cyclobutane-1-carboxylate
• 化学式: C₁₆H₁₈ClNO₃
• 分子量: 307.777
• InChiKey: AZKQKXZFKDZODH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(3-chloro-4-cyanophenoxy)cyclobutanecarboxylate 在 水 、 羟胺 、 三乙胺 、 di(2H-imidazol-2-yl)methanone 作用下， 以 水 、 二甲基亚砜 、 乙酸乙酯 、 乙腈 为溶剂， 反应 19.0h， 生成 trans-3-[3-chloro-4-{5-(5-chloro-6-isopropoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl}phenoxy]cyclobutanecarboxylic acid
  参考文献：
  名称：

  Development of a Scalable Synthesis of Oxadiazole Based S1P₁ Receptor Agonists

  摘要：

  A robust and scalable synthesis was developed for the preparation of oxadiazole based SIP, inhibitors. A new method for the separation of triphenylphosphine oxide from reaction products and an improved method for the synthesis of oxadiazoles in the presence of DBU were incorporated into the process to achieve its scalability.

  DOI：

  10.1021/op300345v
• 作为产物：
  描述：

  2-氯-4-羟基苯甲腈 、 、 三苯基膦 、 偶氮二甲酸二叔丁酯 在 甲醇 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 18.58h， 以to yield 3-(3-Chloro-4-cyano-phenoxy)-cyclobutanecarboxylic acid tert-butyl ester, (6.03 g, 60%) as a white solid的产率得到tert-butyl 3-(3-chloro-4-cyanophenoxy)cyclobutanecarboxylate
  参考文献：
  名称：

  Novel Oxadiazole Compounds

  摘要：

  本发明涉及新型噁二唑类化合物、含有该类化合物的制药组合物，以及将这些化合物或组合物作为S1P家族G蛋白偶联受体的激动剂或拮抗剂，用于治疗与S1P家族受体活性调节相关的疾病，特别是通过提供有益的免疫抑制作用。

  公开号：

  US20110207704A1

文献信息

• [EN] NOVEL OXADIAZOLE COMPOUNDS<br/>[FR] COMPOSÉS INÉDITS D'OXADIAZOLE
  申请人：ABBOTT LAB

  公开号：WO2011071570A1

  公开（公告）日：2011-06-16

  Novel oxadiazole compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions as agonists or antagonists of the S1P family of G protein-coupled receptors for treating diseases associated with modulation of S1P family receptor activity, in particular by affording a beneficial immunosuppressive effect are disclosed.

  新型噁二唑化合物，含有这种化合物的药物组合物以及将这些化合物或组合物用作治疗与调节S1P家族G蛋白偶联受体活性相关的疾病的激动剂或拮抗剂的用途被披露，特别是通过提供有益的免疫抑制作用。
• NOVEL OXADIAZOLE COMPOUNDS
  申请人：Abbott Laboratories

  公开号：EP2509424A1

  公开（公告）日：2012-10-17
• Development of a Scalable Synthesis of Oxadiazole Based S1P₁ Receptor Agonists
  作者：Kirill Lukin、Vimal Kishore、Thomas Gordon

  DOI：10.1021/op300345v

  日期：2013.4.19

  A robust and scalable synthesis was developed for the preparation of oxadiazole based SIP, inhibitors. A new method for the separation of triphenylphosphine oxide from reaction products and an improved method for the synthesis of oxadiazoles in the presence of DBU were incorporated into the process to achieve its scalability.
• Novel Oxadiazole Compounds
  申请人：Cusack Kevin P.

  公开号：US20110207704A1

  公开（公告）日：2011-08-25

  Novel oxadiazole compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions as agonists or antagonists of the S1P family of G protein-coupled receptors for treating diseases associated with modulation of S1P family receptor activity, in particular by affording a beneficial immunosuppressive effect are disclosed.

  本发明涉及新型噁二唑类化合物、含有该类化合物的制药组合物，以及将这些化合物或组合物作为S1P家族G蛋白偶联受体的激动剂或拮抗剂，用于治疗与S1P家族受体活性调节相关的疾病，特别是通过提供有益的免疫抑制作用。