(S)-2-(isopropylhydrazino)-3-phenyl-1-propanol | 915772-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(isopropylhydrazino)-3-phenyl-1-propanol
• CAS: 915772-82-6
• 化学式: C₁₂H₂₀N₂O
• 分子量: 208.304
• InChiKey: ZVIVOEBRTMQACF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.49
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(isopropylhydrazino)-3-phenyl-1-propanol 在 lithium hydride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (5S)-5-benzyl-4-isopropyl-3-(3-phenylpropanoyl)-2H-1,3,4-oxadiazinan-2-one
  参考文献：
  名称：

  Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

  摘要：

  An L-phenylalanine derived oxadiazinanone bearing an isopropyl group at the N-4-position was prepared and acylated with either hydrocinnamoyl or propanoyl chloride. These oxadiazinanones were utilized in titanium-mediated asymmetric aldol reactions with aromatic and aliphatic aldehydes. The diastereoselectivities observed from these reactions ranged from fair to very good and suggested that the N-4-isopropyl-L-phenylalanine based oxadiazinanones are conformationally and configurationally stable at the N-4-nitrogen. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.002
• 作为产物：
  描述：

  (S)-N-(1-hydroxy-3-phenylpropan-2-yl)-N-isopropylnitrous amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-(isopropylhydrazino)-3-phenyl-1-propanol
  参考文献：
  名称：

  Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes

  摘要：

  A series of oxadiazines derived from L-phenylalanine bearing phenolic substituents have been synthesized in a multistep one pot process This process involves the reaction of a mixed anhydride with a beta-hydrazino alcohol methanesulfonylation of the alcohol moiety and base induced cyclization The resultant oxadiazines were employed in the asymmetric addition of diethylzinc to aldehydes (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.09.010

文献信息

• Synthesis and X-ray crystal structures of chiral, nonracemic 5,6-dihydro-4H-1,3,4-oxadiazines
  作者：Shawn R. Hitchcock、Melissa A. Dean、Christopher J. Kelley、Kate L. Edler、Gregory M. Ferrence

  DOI：10.1002/jhet.402

  日期：——

  A series of chiral, nonracemic oxadiazines have been prepared from (1R,2S)‐ephedrine, (1R,2S)‐norephedrine, and L‐phenylalaninol. The synthesis of the Ephedra‐based oxadiazines was accomplished by a process of N‐nitrosation, reduction, acylation, and acid‐catalyzed cyclization. The trans‐ and cis‐diastereomeric oxadiazines derived from (1R,2S)‐ephedrine were analyzed by 1H NMR spectroscopy and by single

  已从（1 R，2 S）-麻黄碱，（1 R，2 S）-去氧麻黄碱和L-苯丙氨醇制备了一系列手性，非外消旋的恶二嗪。基于麻黄的恶二嗪的合成是通过N亚硝化，还原，酰化和酸催化的环化过程完成的。的反式-和CIS衍生自-diastereomeric恶二嗪（1 - [R，2小号） -麻黄碱通过分析1个H NMR光谱和通过单晶X射线晶体学分析。（1 R，2 S）-基于去甲氧麻黄碱的恶二嗪是基于1 H NMR光谱和类似于基于（1 R，2 S）-麻黄碱的恶二嗪的X射线晶体结构进行分配的。另外，以L-苯丙氨醇为模板，制备了一系列在N 4-氮处被异丙基取代的恶二嗪。这是通过将L-苯丙氨醇与丙酮进行还原性烷基化并随后形成酰肼来实现的。这些酰肼与甲磺酰氯通过碱介导的环化反应生成相应的恶二嗪。J.杂环化​​学。（2010）。