(R)-(+)-2-methoxypropionamide | 22543-21-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-(+)-2-methoxypropionamide
• 英文别名: (R)-2-methoxy-propionamide；d(+)-α-methoxy-propionamide；d(+)-α-Methoxy-propionamid；d(+)-O-Methyl-lactamid；(R)-(-)-2-methoxypropionamide；(2R)-2-methoxypropanamide
• CAS: 22543-21-1
• 化学式: C₄H₉NO₂
• 分子量: 103.121
• InChiKey: WOGXHNJBKGZMHV-GSVOUGTGSA-N

物化性质

• 熔点：
  81 °C
• 沸点：
  102-110 °C(Press: 2 Torr)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-methoxypropionamide 在 磷酸酐 作用下， 以44%的产率得到(R)-(+)-2-甲氧基丙腈
  参考文献：
  名称：

  Sorbitol Dehydrogenase Inhibitors (SDIs):  A New Potent, Enantiomeric SDI, 4-[2-1R-Hydroxy-ethyl)-pyrimidin-4-yl]-piperazine-1-sulfonic Acid Dimethylamide

  摘要：

  We report here on our medicinal chemistry and pharmacology efforts to provide a potent sorbitol dehydrogenase inhibitor (SDI) as a tool to probe a recently disclosed hypothesis centered on the role of sorbitol dehydrogenase (SDH) in the second step of the polyol pathway, under conditions of high glucose flux. Starting from a weak literature lead, 2, and through newly developed structure-activity relationships, we have designed and executed an unambiguous synthesis of enantiomeric SDI, 6, which is at least 10x more potent than 2. Also, 6 potently inhibits SDH in streptozotocin-diabetic rat sciatic nerve. We have described an expedient synthesis of a key building template, 33, for future research in the SDI area that may facilitate the discovery of even more potent SDIs with longer duration of action in vivo.

  DOI：

  10.1021/jm0102001
• 作为产物：
  描述：

  R-(+)-2-methoxypropionic acid chloride 在 氨 、 苯 作用下， 生成 (R)-(+)-2-methoxypropionamide
  参考文献：
  名称：

  Freudenberg; Markert, Chemische Berichte, 1927, vol. 60, p. 2447

  摘要：

  DOI：

文献信息

• Bromoporphyrins as Versatile Synthons for Modular Construction of Chiral Porphyrins:  Cobalt-Catalyzed Highly Enantioselective and Diastereoselective Cyclopropanation
  作者：Ying Chen、Kimberly B. Fields、X. Peter Zhang

  DOI：10.1021/ja044889l

  日期：2004.11.1

  to be versatile synthons for modular construction of chiral porphyrins via palladium-catalyzed amidation reactions with chiral amides. The quadruple carbon-nitrogen bond formation reactions were accomplished in high yields with different chiral amide building blocks under mild conditions, forming a family of D2-symmetric chiral porphyrins. Cobalt(II) complexes of these chiral porphyrins were prepared

  5,10-双(2',6'-二溴苯基)卟啉在 10 和 20 位具有各种取代基，被证明是通过钯催化的手性酰胺酰胺化反应模块化构建手性卟啉的通用合成子。在温和的条件下，使用不同的手性酰胺结构单元以高产率完成了四重碳氮键形成反应，形成了 D2 对称手性卟啉家族。这些手性卟啉的钴 (II) 配合物以高产率制备，并且在实用的一锅法（烯烃作为限制性试剂且不缓慢添加重氮试剂）下显示为高对映选择性和非对映选择性环丙烷化的活性催化剂。
• Cobalt-based catalysts for the cyclization of alkenes
  申请人：Zhang Peter X.

  公开号：US20060030718A1

  公开（公告）日：2006-02-09

  Metal-ligand complexes, including cobalt-ligand complexes, such as a cobalt-porphyrin complex, and their use as catalysts in the cyclization of alkenes.

  金属配合物，包括钴配体配合物，如钴卟啉配合物，以及它们在烯烃环化反应中作为催化剂的使用。
• Freudenberg; Markert, Chemische Berichte, 1927, vol. 60, p. 2447
  作者：Freudenberg、Markert

  DOI：——

  日期：——
• Sorbitol Dehydrogenase Inhibitors (SDIs):  A New Potent, Enantiomeric SDI, 4-[2-1<i>R</i>-Hydroxy-ethyl)-pyrimidin-4-yl]-piperazine-1-sulfonic Acid Dimethylamide
  作者：Banavara L. Mylari、Peter J. Oates、David A. Beebe、Nathaniel S. Brackett、James B. Coutcher、Michael S. Dina、William J. Zembrowski

  DOI：10.1021/jm0102001

  日期：2001.8.1

  We report here on our medicinal chemistry and pharmacology efforts to provide a potent sorbitol dehydrogenase inhibitor (SDI) as a tool to probe a recently disclosed hypothesis centered on the role of sorbitol dehydrogenase (SDH) in the second step of the polyol pathway, under conditions of high glucose flux. Starting from a weak literature lead, 2, and through newly developed structure-activity relationships, we have designed and executed an unambiguous synthesis of enantiomeric SDI, 6, which is at least 10x more potent than 2. Also, 6 potently inhibits SDH in streptozotocin-diabetic rat sciatic nerve. We have described an expedient synthesis of a key building template, 33, for future research in the SDI area that may facilitate the discovery of even more potent SDIs with longer duration of action in vivo.