(S)-1-(allyloxy)-3-phenylpropan-2-amine | 1440196-22-4

• 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)-1-(allyloxy)-3-phenylpropan-2-amine
• 英文别名: (2S)-1-phenyl-3-prop-2-enoxypropan-2-amine
• CAS: 1440196-22-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: XKPJEEMBYHUHEJ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(allyloxy)-3-phenylpropan-2-amine 在 ethylene dichloride hydrochloride 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 (2S)-N-[(2S)-1-phenyl-3-prop-2-enoxypropan-2-yl]piperidine-2-carboxamide
  参考文献：
  名称：

  Stereoselective Synthesis of Rapamycin Fragment To Build a Macrocyclic Toolbox

  摘要：

  A stereoselective synthesis of a rapamycin fragment is developed and further utilized toward building a macrocyclic chemical toolbox. The amino alcohol moiety embedded in the 22-membered macrocyclic ring allowed for the addition of a variation in the chiral side chain. The key reactions leading to the synthesis of the rapamycin-derived pyran fragment include the following: (i) Paterson aldol, (ii) stereoselective β-OH carbonyl reduction, and (iii) regio- and stereoselective intramolecular oxy-Michael reaction. The other piece needed for building the macrocyclic diversity was obtained from the coupling of various amino alcohol moieties with S-pipecolic acid.

  DOI：

  10.1021/ol5034833
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醇 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (S)-1-(allyloxy)-3-phenylpropan-2-amine
  参考文献：
  名称：

  从 C-Linked 碳水化合物构建大环工具箱，从斑马鱼测定中识别抗血管生成剂

  摘要：

  我们报告了从碳水化合物合成四种不同类型的大环衍生糖杂化物，这些碳水化合物在大环骨架中具有氨基酸部分。这些大环糖杂化物是...

  DOI：

  10.1002/ejoc.201300548

文献信息

• Tetrahydroquinoline-Derived Macrocyclic Toolbox: The Discovery of Antiangiogenesis Agents in Zebrafish Assay
  作者：Shiva Krishna Reddy Guduru、Srinivas Chamakuri、Gayathri Chandrasekar、Satish Srinivas Kitambi、Prabhat Arya

  DOI：10.1021/ml400026n

  日期：2013.7.11

  incorporate the macrocyclic rings onto the privileged substructure, i.e., tetrahydroquinoline scaffold, is developed. The presence of an amino acid-derived moiety in the macrocyclic skeleton provides an opportunity to modulate the nature of the chiral side chain. Further, evaluation in a zebrafish screen identified three active small molecules (2.5b, 3.2d, and 4.2) as antiangiogenesis agents at 2.5 muM

  开发了一种将大环结合到特权子结构（即四氢喹啉骨架）上的新颖方法。大环骨架中氨基酸衍生部分的存在为调节手性侧链的性质提供了机会。此外，在斑马鱼筛选中的评估确定了三个活性小分子（2.5b，3.2d和4.2）为2.5μM的抗血管生成剂。
• Practical Stereoselective Synthesis of Eribulin Fragment toward Building a Hybrid Macrocyclic Toolbox
  作者：Ravikumar Jimmidi、Shiva Krishna Reddy Guduru、Prabhat Arya

  DOI：10.1021/ol503464s

  日期：2015.2.6

  A practical stereoselective synthesis to obtain the substituted furan ring as the substructure of eribulin is developed. An asymmetric syn-aldol and intramolecular oxy-Michael were two key steps in our approach. The functionalized furan derivatives were then utilized further to build the 14- and 12-membered macrocyclic diversity as trans- and cis-fused (C-29 and C-30) compounds. This is the first report

  开发了一种实用的立体选择性合成方法，以获得取代的呋喃环作为eribulin的亚结构。不对称的顺式羟醛和分子内的氧-迈克尔是我们方法中的两个关键步骤。然后将官能化的呋喃衍生物进一步利用构建14-和12-元大环多样性反式-和顺-融合（C-29和C-30）的化合物。这是首次建立具有大环小分子的化学工具箱的化学工具箱，该大环小分子具有包含eribulin及其非对映异构体亚结构的反式或顺式稠合的14或12元环。
• Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan
  作者：Margherita Pirola、Alessandra Puglisi、Laura Raimondi、Alessandra Forni、Maurizio Benaglia

  DOI：10.3390/molecules24122260

  日期：——

  agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation

  已经分批研究了一种立体选择性合成策略，用于制备三氟甲胺模拟物的三氟甲胺模拟物，涉及非对映选择性、无金属催化步骤，并以良好的收率和高非对映选择性提供目标分子。合成顺序的一个关键点是在手性路易斯碱的存在下用三氯硅烷作为还原剂催化还原氟化烯胺。通过 X 射线分析明确指定了关键中间体的绝对构型。还研究了利用连续流动反应的合成；也就是说，目标分子的高级中间体仅在两个流入合成模块中合成，避免了中间体的分离和纯化，
• N-Heterocyclic Carbene-Catalyzed Highly Enantioselective Macrolactonization to Access Planar-Chiral Macrocycles
  作者：Jiaming Wang、Meng Wang、Yilu Wen、Peng Teng、Chenyang Li、Changgui Zhao

  DOI：10.1021/acs.orglett.3c04200

  日期：2024.2.9

  An N-heterocyclic carbene (NHC)-catalyzed atroposelective macrolactonization has been disclosed. This approach affords planar-chiral macrocycles in high yields with excellent enantioselectivities over a broad substrate scope. Controlled experiments suggest that the enantioselectivity might arise from the cation–n interaction between the acyl azolium and the electron-rich moiety in the substrate. This

  已经公开了N-杂环卡宾(NHC)催化的阻转选择性大内酯化。这种方法能够以高产率提供平面手性大环化合物，并在广泛的底物范围内具有优异的对映选择性。对照实验表明，对映选择性可能源于酰基唑鎓与底物中富电子部分之间的阳离子-n相互作用。该机制得到了密度泛函理论计算的支持，这也表明了稳定过渡态中重要的 π-π 相互作用。