N-(1,4-dioxaspiro[4.5]dec-8-ylmethyl)acetamide | 299180-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(1,4-dioxaspiro[4.5]dec-8-ylmethyl)acetamide
• 英文别名: N-(1,4-dioxaspiro[4.5]decan-8-ylmethyl)acetamide
• CAS: 299180-11-3
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: XMNMVLBNESBOST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1,4-dioxaspiro[4.5]dec-8-ylmethyl)acetamide 在 氢氧化钾 、 甲酸 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 (+/-)-N-[(2-acetyl-4,5,6,7-tetrahydro-2H-izoindol-5-yl)methyl]acetamide
  参考文献：
  名称：

  A general synthetic approach to novel conformationally restricted arginine side chain mimetics

  摘要：

  A general synthesis of several novel partially saturated, conformationally restricted heterobicyclic arginine side chain mimetics is described. These compounds are interesting peptidomimetic building blocks for incorporation into trypsin-like serine protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01243-1
• 作为产物：
  描述：

  4-氰基环己酮缩乙二醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(1,4-dioxaspiro[4.5]dec-8-ylmethyl)acetamide
  参考文献：
  名称：

  A general synthetic approach to novel conformationally restricted arginine side chain mimetics

  摘要：

  A general synthesis of several novel partially saturated, conformationally restricted heterobicyclic arginine side chain mimetics is described. These compounds are interesting peptidomimetic building blocks for incorporation into trypsin-like serine protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01243-1

文献信息

• Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents
  作者：Noah Wagner-Carlberg、Tomislav Rovis

  DOI：10.1021/jacs.2c10552

  日期：2022.12.14

  general method for the intermolecular anti-Markovnikov hydroamidation of unactivated alkenes under mild conditions, utilizing Rh(III) catalysis in conjunction with dioxazolone amidating reagents and isopropanol as an environmentally friendly hydride source. The reaction tolerates a wide range of functional groups and efficiently converts electron-deficient alkenes, styrenes, and 1,1-disubstituted alkenes

  酰胺是所有药物中最常见的官能团之一，因此，引入酰胺部分的反应具有特别的价值。烯烃的分子间加氢酰胺化仍然是一种尚未充分探索的合成含酰胺化合物的方法。大多数氢酰胺化过程表现出马尔可夫尼科夫区域选择性，而目前的反马尔可夫尼科夫氢酰胺化方法在某种程度上仅限于活化的烯烃底物或自由基过程。在此，我们报告了一种在温和条件下对未活化的烯烃进行分子间反马可夫尼科夫氢酰胺化的通用方法，利用Rh(III)催化结合二恶唑酮酰胺化试剂和异丙醇作为环境友好的氢化物源。该反应可耐受多种官能团，可有效地将缺电子烯烃、苯乙烯和 1,1-二取代烯烃以及未活化的烯烃转化为相应的直链酰胺。机理研究揭示了可逆的氢化铑迁移插入步骤，从而导致抗马可夫尼科夫产物具有精细的选择性。
• A general synthesis of novel conformationally restricted arginine side-chain mimetics
  作者：Lucija P Mašič、Danijel Kikelj

  DOI：10.1016/s0040-4039(00)00869-8

  日期：2000.7

  6-(Aminomethyl)-5,6,7,8-tetrahydro-2-quinazolinamine and 4,5,6,7-tetrahydro-2H-indazol-5-ylmethanamine were synthesized as novel conformationally restricted arginine side-chain mimetics, designed for incorporation into trypsin-like serine protease inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.
• US7524871B2
  申请人：——

  公开号：US7524871B2

  公开（公告）日：2009-04-28
• A general synthetic approach to novel conformationally restricted arginine side chain mimetics
  作者：Lucija Peterlin-Mašič、Andreja Jurca、Petra Marinko、Anita Jančar、Danijel Kikelj

  DOI：10.1016/s0040-4020(01)01243-1

  日期：2002.2

  A general synthesis of several novel partially saturated, conformationally restricted heterobicyclic arginine side chain mimetics is described. These compounds are interesting peptidomimetic building blocks for incorporation into trypsin-like serine protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.