tert-butyl (2S)-2-[(2R)-2-hydroxypropyl]pyrrolidine-1-carboxylate | 1350627-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S)-2-[(2R)-2-hydroxypropyl]pyrrolidine-1-carboxylate
• 英文别名: (S)-tert-butyl 2-((R)-2-hydroxypropyl)pyrrolidine-1-carboxylate；(2S)-tert-butyl 2-[(2R)-2-hydroxypropyl]pyrrolidine-1-carboxylate
• CAS: 1350627-37-0
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: PEIYIQMKMZTUHV-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(2R)-2-hydroxypropyl]pyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以87%的产率得到(2R)-1-[(2S)-1-methylpyrrolidin-2-yl]propan-2-ol
  参考文献：
  名称：

  Total Synthesis of Hygrolines and Pseudohygrolines

  摘要：

  A concise two-step synthesis of all four diastereoisomeric hygrolines ((-)-hygroline (1), (+)-hygroline (2), (-)-pseudohygroline (3), (+)-pseudohygroline (4)) has been developed based on the (-)-sparteine (5)- or (+)-sparteine surrogate 11-mediated enantioselective lithiation of N-Boc pyrrolidine (6), followed by reaction of the chiral anion with (S)- or (R)-propylene oxide. Reduction of the resulting N-Boc amino alcohols furnished hygrolines and pseudohygrolines in 30% to 56% overall yields with dr's > 95:5.

  DOI：

  10.1021/jo4017343
• 作为产物：
  描述：

  (S)-tert-butyl 2-(2-(methoxy(methyl)amino)-2-oxoethyl)pyrrolidine-1-carboxylate 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 tert-butyl (2S)-2-[(2R)-2-hydroxypropyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Conioidine A 的合成和立体化学分配：四种非对映异构体的 DNA 和 HSA 结合研究

  摘要：

  Conioidine A ( 1 ) 于 1993 年以未知的相对和绝对构型分离出来，通过间接技术被认为是一种 DNA 结合化合物。已从d - 和l - 脯氨酸合成了 conioidine A 的四种立体异构体，并且已确定天然产物具有 (4 R ,6 R ) 绝对构型。已经通过荧光光谱法和等温滴定量热法 (ITC) 研究了 conioidine 非对映异构体与小牛胸腺 DNA (CT DNA) 和人血清白蛋白 (HSA) 的结合。所有立体异构体与 DNA 的结合至少比对照化合物 netropsin 弱一个数量级；然而，观察到 (4 R,6 S ) 立体异构体。

  DOI：

  10.1021/acs.jnatprod.0c00871

文献信息

• Henry–Nef reaction: a practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
  作者：Chinmay Bhat、Santosh G. Tilve

  DOI：10.1016/j.tet.2013.05.055

  日期：2013.7

  for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (−)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key

  本文描述了由亨利和Nef组合反应开发的协同方案，用于合成含有1,3-氨基酮和1,3-氨基醇单元的2-取代的吡咯烷和哌啶生物碱。该协议的实用性通过12种天然产物的不对称合成得到了证明，其中首次出现了（-）- N-甲基胆碱的不对称合成。所描述的一碳同系物还提供了另一种合成关键中间体高脯氨醇和高胡椒醇的中间体的途径，这些中间体用作几种生物碱的合成前体，并由α-氨基酸构建β-氨基酸。
• Synthetic Studies of Alkaloids Containing Pyrrolidine and Piperidine Structural Motifs
  作者：Chinmay Bhat

  DOI：10.1002/open.201402128

  日期：2015.4

  Avenues to asymmetric alkaloids! Various 2‐substituted pyrrolidine and piperidine chiral bioactive natural products were synthesized using a ‘chiral pool’ method. l‐proline and l‐pipecolinic acids with one chiral center served as the best precursors for the synthesis of these alkaloids. Overall, 14 total synthetic and 11 formal synthetic approaches were developed.

  不对称生物碱的大道！使用“手性库”方法合成了各种2-取代的吡咯烷和哌啶手性生物活性天然产物。带有一个手性中心的l-脯氨酸和l- pipecolinic酸是合成这些生物碱的最佳前体。总的来说，共开发了14种综合合成方法和11种正式合成方法。
• Synthesis of (−)-hygrine, (−)-norhygrine, (−)-pseudohygroline and (−)-hygroline via Nef reaction
  作者：Chinmay Bhat、Santosh G. Tilve

  DOI：10.1016/j.tetlet.2011.09.118

  日期：2011.12

  Synthesis of tropane alkaloids (-)-hygrine, (-)-norhygrine and sedum alkaloids (-)-pseudohygroline and (-)-hygroline is described from L-proline via Henry and Nef reactions. (C) 2011 Elsevier Ltd. All rights reserved.
• A generic small-molecule microarray immobilization strategy
  作者：Mariona Vallès-Miret、Mark Bradley

  DOI：10.1016/j.tetlet.2011.10.055

  日期：2011.12

  Small-molecule microarrays are often limited by the requirement for each compound undergoing immobilization to contain a common functional group or by the need to prepare glass slides containing photo-reactive groups. Herein, we present a generic strategy that allows any compound library to be immobilized. This was achieved by printing a fluorous-tagged photo-reactive 3-aryl-3-trifluoromethyldiazirine, which undergoes non-selective insertion into compounds following UV-activation, onto fluorous-functionalized glass slides. The arrays could be reused following aqueous stripping and re-assessment of the compounds with the same protein or another target of interest. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.