(2S,3R)-1-Ethyl-3-(2-methylbutyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3R)-1-Ethyl-3-(2-methylbutyl)piperidine
• 英文别名: (2’S,3S)-stenusine；(2'S,3S)-stenusine；(2S,3S)-stenusine；(S,S)-Stenusine；Stenusine；(3S)-1-ethyl-3-[(2S)-2-methylbutyl]piperidine
• 化学式: C₁₂H₂₅N
• 分子量: 183.337
• InChiKey: DYZADDXQHPDPNW-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基吡啶 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 氢气 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (2S,3R)-1-Ethyl-3-(2-methylbutyl)piperidine
  参考文献：
  名称：

  Short synthesis of stenusine and norstenusine, two spreading alkaloids from Stenus beetles (Coleoptera: Staphylinidae)

  摘要：

  Each of the both spreading alkaloids stenusine and norstenusine could be synthesized starting from commercially available 3-picoline in a two-step synthesis in yields of 74% and 67% in gram scale. The stereoisomeric ratio of the synthesized (+)-stenusine is similar to that of stenusine from Stenus comma. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.024

文献信息

• Straightforward Synthesis of All Stenusine and Norstenusine Stereoisomers
  作者：Tobias Müller、Konrad Dettner、Karlheinz Seifert

  DOI：10.1002/ejoc.201100612

  日期：2011.10

  All the stereoisomers of stenusine (1) and norstenusine (21) have been efficiently synthesized by the asymmetric hydrogenation of pyridines. The (2R,3S)- and (2R,3R)-isomers of 1, that are difficult to prepare, have been synthesized for the first time using a chemoenzymatic approach in eight steps with an 8 % total yield. All the target compounds were obtained in good stereochemical purity by using

  stenusine (1) 和norstenusine (21) 的所有立体异构体都已通过吡啶的不对称氢化有效合成。难以制备的 (2R,3S)- 和 (2R,3R)-异构体 1 已首次使用化学酶法分八步合成，总产率为 8%。通过使用非常简单和廉价的试剂和助剂，所有目标化合物均以良好的立体化学纯度获得。
• An Expeditious Total Synthesis of the Natural Stereomeric Mixture of Stenusine Following a Possible Biogenetic Pathway
  作者：Erwan Poupon、Nicole Kunesch、Henri‐Philippe Husson

  DOI：10.1002/(sici)1521-3773(20000417)39:8<1493::aid-anie1493>3.0.co;2-#

  日期：2000.4.17
• Enantioselective synthesis and determination of the configuration of stenusine, the spreading agent of the beetle Stenus comma
  作者：Dieter Enders、Joerg Tiebes、Norbert De Kimpe、Marian Keppens、Christian Stevens、Guy Smagghe、Oliver Betz

  DOI：10.1021/jo00070a024

  日期：1993.8

  The enantioselective total synthesis of two of the four possible stereoisomers of stenusine (1), the spreading agent of the beetle Stenus comma, is described. The silyl ether-substituted aldehyde SAMP hydrazone 2 was alkylated with (S)-1-bromo-2-methylbutane (3) yielding the hydrazone 4 in high diastereomeric purity (de >95 %). By several steps including the reduction of the hydrazone functionality and the cleavage of the N-N bond of the intermediates, 4 was converted into the BOC-protected amino alcohol 6. Subsequent cyclization of 6 afforded the (S,S) diastereomer of stenusine with 96.6 % de, >99.9 % ee, and in 11.3 % overall yield. Repetition of this synthesis using the aldehyde RAMP hydrazone (R)-2 as the starting material produced (SR)-1 with 95.0 % de, >99 % ee, and in 8.2 % overall yield. The synthetic samples of 1 were employed to investigate the stereochemistry of natural stenusine by means of GC analysis on both a chiral and an achiral, stationary phase. As a result of these studies natural stenusine was found to be a mixture of all four stereoisomers in a ratio of (S,S)/(SR)/(RR)/(R:S) = 43:40:13:4.
• Short synthesis of stenusine and norstenusine, two spreading alkaloids from Stenus beetles (Coleoptera: Staphylinidae)
  作者：Thomas Gedig、Konrad Dettner、Karlheinz Seifert

  DOI：10.1016/j.tet.2007.01.024

  日期：2007.3

  Each of the both spreading alkaloids stenusine and norstenusine could be synthesized starting from commercially available 3-picoline in a two-step synthesis in yields of 74% and 67% in gram scale. The stereoisomeric ratio of the synthesized (+)-stenusine is similar to that of stenusine from Stenus comma. (c) 2007 Elsevier Ltd. All rights reserved.