2-Hydrazino-2-hydroxymethyl-propane-1,3-diol | 887591-91-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Hydrazino-2-hydroxymethyl-propane-1,3-diol
• 英文别名: 2-Hydrazinyl-2-(hydroxymethyl)-1,3-propanediol；2-hydrazinyl-2-(hydroxymethyl)propane-1,3-diol
• CAS: 887591-91-5
• 化学式: C₄H₁₂N₂O₃
• mdl: MFCD07786251
• 分子量: 136.151
• InChiKey: SGOQPVNCESJGKF-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  98.7
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Hydrazino-2-hydroxymethyl-propane-1,3-diol 、 1-[(1R,3R,4R,5S,6R,7R,8R,9R)-5,7-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-ethanone 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以70%的产率得到2-{N'-[1-[(1S,3R,4S,5S,6R,7R,8R,9R)-5,7-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-eth-(E)-ylidene]-hydrazino}-2-hydroxymethyl-propane-1,3-diol
  参考文献：
  名称：

  Approach towards an EPC-synthesis of nodusmicin-IV. Construction of the highly hindered trisubstituted double bond of nodusmicin

  摘要：

  The highly substituted subunit 6 of our convergent synthesis of nodusmicin was prepared utilizing Evans' oxazolidinone protocol. Compound 6 was then adjoined to the decalin subunit 7 using Martin's olefination method. To improve on the formation of the hindered trisubstituted double bond, the following model reactions were devised: reductive coupling of ester and keto functionality of tricycle 16 led to the alpha-hydroxyketone, which was converted to the cyclic sulfate 19 via the diol. Sodium naphthalide then converted 19 to the olefins 20. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01521-9

文献信息

• Development of a Concise Synthesis of Ouabagenin and Hydroxylated Corticosteroid Analogues
  作者：Hans Renata、Qianghui Zhou、Georg Dünstl、Jakob Felding、Rohan R. Merchant、Chien-Hung Yeh、Phil S. Baran

  DOI：10.1021/ja512022r

  日期：2015.1.28

  The natural product ouabagenin is a complex cardiotonic steroid with a highly oxygenated skeleton. This full account describes the development of a concise synthesis of ouabagenin, including the evolution of synthetic strategy to access hydroxylation at the C19 position of a steroid skeleton. In addition, approaches to install the requisite butenolide moiety at the C17 position are discussed. Lastly

  天然产物瓦巴根配基是一种复杂的强心类固醇，具有高度含氧的骨架。这篇完整的叙述描述了瓦巴根配基的简明合成的发展，包括在类固醇骨架的 C19 位置进行羟基化的合成策略的演变。此外，还讨论了在 C17 位置安装必需的丁烯酸内酯部分的方法。最后，该合成中开发的方法已应用于生成在 C19 位置带有羟基的皮质类固醇药物的新型类似物。