3-amino-2-butanol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-amino-2-butanol
• 英文别名: (+/-)-erythro-3-amino-butanol-(2)；(2S,3R)-3-aminobutan-2-ol
• 化学式: C₄H₁₁NO
• 分子量: 89.1374
• InChiKey: FERWBXLFSBWTDE-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-2-butanol 在 硫酸 作用下， 生成 sulfuric acid mono-((1RS,2SR)-2-amino-1-methyl-propyl) ester
  参考文献：
  名称：

  The Reactions of -Aminoalkyl Hydrogen Sulfates. I. The Preparation of Some Substituted Thiazolidine-2-thiones¹

  摘要：

  DOI：

  10.1021/jo01013a046
• 作为产物：
  描述：

  2,3-trans-epoxybutane 在 ammonium hydroxide 作用下， 生成 3-amino-2-butanol
  参考文献：
  名称：

  邻苯二甲酰亚胺二烯II。顺式和反式-2,3-二甲基-1-邻苯二甲酰亚胺基-氮丙啶。合成与溶剂分解† ‡

  摘要：

  邻苯二甲酰亚胺II 1 。顺式和反式-2,3-二甲基-1-邻苯二甲酰亚胺基氮丙啶。合成与溶剂分解反应2

  DOI：

  10.1002/hlca.19750580714

文献信息

• Direct synthesis of novel 2-imino-1,3-selenazolidine derivatives from O-methanesulfonyl β-amino alcohol hydrochlorides
  作者：Shigeo Ueda、Hideo Terauchi、Kenji Suzuki、Nobuhide Watanabe

  DOI：10.1016/j.tetlet.2004.11.064

  日期：2005.1

  nitric oxide synthase (iNOS). To our knowledge, only few methods have been reported for the synthesis of 4,5-dialkylsubstituted 2-imino-1,3-selenazolidine derivatives (2), which are the selenium analogue of 1. Herein, we report the direct synthesis of 2 from the corresponding O-methanesulfonyl β-amino alcohol hydrochlorides using potassium selenocyanate and evaluation for the inhibitory activity against

  最近，我们已经报道了4，5-二烷基取代的2-亚氨基-1，3-氮杂环丁烷衍生物（1）强烈抑制诱导型一氧化氮合酶（iNOS）。据我们所知，只有很少的方法已被报道用于4,5-二烷基取代的2-亚氨基-1,3- selenazolidine衍生物（合成2），这是的硒类似物1。在此，我们报道了使用硒氰酸钾从相应的O-甲磺酰基β-氨基醇盐酸盐直接合成2，并评估了新合成硒代硒唑烷衍生物对iNOS的抑制活性。
• Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers
  作者：Moriyasu Masui、Takayuki Shioiri

  DOI：10.1016/s0040-4039(98)01019-3

  日期：1998.7

  Asymmetric reduction of α-oxoketoxime ethers with the reagents prepared in situ from trimethyl borate and chiral amino alcohols derived from either L-proline or α-pinene was investigated. Both cyclic and acyclic α-oxoketoxime ethers were reduced to afford the corresponding chiral 1,2-amino alcohols with high enantioselectivities.

  研究了用由硼酸三甲酯和衍生自L-脯氨酸或α-chi烯的手性氨基醇原位制备的试剂对α-氧肟肟醚的不对称还原。环状和无环α-氧代肟醚都被还原，得到相应的具有高对映选择性的手性1,2-氨基醇。
• Bafford,R.A. et al., Bulletin de la Societe Chimique de France, 1973, p. 971 - 977
  作者：Bafford,R.A. et al.

  DOI：——

  日期：——
• Efficient Preparation of Biologically Important 1,2-Amino Alcohols
  作者：Pankaj Gupta、Abdul Rouf、Bhahwal A. Shah、Debaraj Mukherjee、Subhash C. Taneja

  DOI：10.1080/00397911.2011.603876

  日期：2013.1.1

  An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced alpha-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60 degrees C to yield biologically important 1,2-amino alcohols.
• Reaction of .alpha.-diketones with 2-amino alcohols. Intramolecular competitive 6-exo-trig vs 5-endo-trig processes. A systematic and kinetic study
  作者：Benito Alcaide、Joaquin Plumet、Ignacio M. Rodriguez-Campos、Severino Garcia-Blanco、Sagrario Martinez-Carrera

  DOI：10.1021/jo00034a046

  日期：1992.4

  2-Aminoethanol and C-substituted derivatives 1 react with diacetyl, benzil, and 1-phenyl-1,2-propanedione, models of alpha-diketones 2 to give with remarkable regio- and stereoselectivity 2-hydroxy-5,6-dihydro-2H-1,4-oxazines 3, cis-octahydro[1,4]oxazino[3,2-b]oxazines 4, alpha-imino ketones 6, 2-acetyl-1,3-oxazolidines 7, N,N'-bis(2-hydroxy-2-methylpropyl)-2,3-butanediimines 8, and 2,2'-dimethyl-2,2'-bioxazolidines 9 depending on the nature of the reagents and the reaction conditions. On the basis of isolated intermediates, a reasonable mechanism taking into account the stereoelectronic effects observed on the cyclization has been proposed for these processes. In addition, a kinetic study of the ring-chain-ring tautomeric equilibrium of oxazines 3a-c, 3i-k, and 3o-q has been studied by H-1 NMR and C-13 NMR. In solution, compounds 3a-c and 3i-k exhibit a three-component tautomeric equilibria consisting of the following: the beta-iminohemiacetal 3, the beta-hydroxyimino ketone 6, and the 2-acetyl- or 2-benzoyl-1,3-oxazolidine 7. The calculated rate constants for this process show that the equilibrium is shifted toward the formation of the five-membered ring by 0.4-4.8 kJ mol-1 over the six-membered ring depending on the substitution patterns. Compounds 3p-q exist in solution as equimolar mixtures of the ring and open-chain tautomers. Compound 3o exists predominantly in the open-chain form. In addition, 2-acylthiazolidines 13a-c do not evidence any dynamic processes in solution.