ethyl 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetate | 36691-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetate
• 英文别名: N-[4-(carbethoxymethyl)-phenyl]-phthalimide；Ethyl 2-[4-(1,3-dioxoisoindol-2-yl)phenyl]acetate
• CAS: 36691-06-2
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: CJORTZHHUZARCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetate 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2-(4-氨基苯基)丙酸乙酯
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132
• 作为产物：
  描述：

  苯酐 、 4-氨基苯乙酸乙酯 以 溶剂黄146 为溶剂， 反应 18.0h， 生成 ethyl 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetate
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132

文献信息

• A Facile Deprotection of Secondary Acetamides
  作者：Stefan G. Koenig、Charles P. Vandenbossche、Hang Zhao、Patrick Mousaw、Surendra P. Singh、Roger P. Bakale

  DOI：10.1021/ol802482d

  日期：2009.1.15

  Imidoyl chlorides, generated from secondary acetamides and oxalyl chloride, can be harnessed for a selective and practical deprotection sequence. Treatment of these intermediates with 2 equiv of propylene glycol and warming enables the rapid release of amine hydrochloride salts in good yields. Notably, the reaction conditions are mild enough to allow for a swift deprotection with no observed epimerization

  由仲乙酰胺和草酰氯产生的亚氨基酰氯可用于选择性和实用的脱保护顺序。用2当量的丙二醇处理这些中间体并加热可快速释放胺盐酸盐，且收率高。值得注意的是，反应条件温和到足以允许快速脱保护而没有观察到氨基中心的差向异构化。
• US4118504A
  申请人：——

  公开号：US4118504A

  公开（公告）日：1978-10-03
• Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors
  作者：Kenji Yoshikawa、Toshiharu Yoshino、Yoshihiro Yokomizo、Kouichi Uoto、Hiroyuki Naito、Katsuhiro Kawakami、Akiyoshi Mochizuki、Tsutomu Nagata、Makoto Suzuki、Hideyuki Kanno、Makoto Takemura、Toshiharu Ohta

  DOI：10.1016/j.bmcl.2011.01.132

  日期：2011.4

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.