[2α(1E,3E),4β]-2-(1,3-pentadienyl)-4-piperidinol

• 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: [2α(1E,3E),4β]-2-(1,3-pentadienyl)-4-piperidinol
• 英文别名: (2S,4S)-(-)-2-(penta-1',3'-dienyl)piperidin-4-ol；(2S,4S)-(-)-SS20846A；(2S,4S)-2-[(1E,3E)-penta-1,3-dienyl]piperidin-4-ol
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: HUJDEHIXVKEMDT-OOPZPQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4-己二烯醛 在 titanium(IV) tetraethanolate 、 lithium aluminium tetrahydride 、 zinc(II) tetrahydroborate 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 [2α(1E,3E),4β]-2-(1,3-pentadienyl)-4-piperidinol
  参考文献：
  名称：

  δ-氨基β-酮酸酯，一种为生物碱合成设计的多官能度手性结构单元。（R）-（+）-2-苯基哌啶和（-）-SS20846A的不对称合成。

  摘要：

  [公式：见正文]δ-氨基β-酮酸酯3和11是为生物碱合成设计的多官能手性结构单元，由相应的亚磺胺（N-亚磺酰基亚胺）一步制备。分别描述了分别由3和11合成的2-苯基哌啶（7）和SS20846A（14）的简明高对映选择性四步合成方法。

  DOI：

  10.1021/ol005580j

文献信息

• Diastereoselective [4 + 2] type cycloaddition of 1-azatriene iron-tricarbonyl complex: Asymmetric synthesis of a piperidien alkaloid
  作者：Yoshiji Takemoto、Shigeo Ueda、Jun Takeuchi、Takahisa Nakamoto、Chuzo Iwata

  DOI：10.1016/s0040-4039(00)78507-8

  日期：1994.11

  A LiClO4 catalyzed cycloaddition reaction of 1-azatriene iron-tricarbonyl complex 2b with Danishefsky's diene proceeds in highly stereoselective manner to give diastereomerically pure 2-substituted dehydropiperidinone derivative 3b. The chiral cycloadduct 3b* is converted into a biologically active piperidine alkaloid SS20846A in 3 steps, by which its absolute configuration is revealed as 2S,4S.

  1-氮杂三烯铁-三羰基络合物2b与Danishefsky's二烯的LiClO 4催化的环加成反应以高度立体选择性的方式进行，得到非对映体纯的2-取代的脱氢哌啶酮衍生物3b。手性环加成3B *被转换成具有生物活性的哌啶生物碱SS20846A在3个步骤，通过该其绝对构型被揭示为2小号，4小号。
• Total synthesis of SS20846A via intramolecular Pd(II)-catalyzed cyclization
  作者：Hajime Yokoyama、Kumiko Otaya、Seiji Yamaguchi、Yoshiro Hirai

  DOI：10.1016/s0040-4039(98)01225-8

  日期：1998.8

  A stereoselective total synthesis of SS20846A was efficiently accomplished by means of an intramolecular palladium(II)-catalyzed cyclization. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Efficient Chiral Induction by Diene Iron-Tricarbonyl Moiety. IV.: Asymmetric Total Synthesis of a Piperidine Alkaloid, SS20846A.
  作者：Yoshiji TAKEMOTO、Shigeo UEDA、Jun TAKEUCHI、Yasutaka BABA、Chuzo IWATA

  DOI：10.1248/cpb.45.1906

  日期：——

  By LiClO4-catalyzed cycloaddition with Danishefsky's diene 5, an optically active 1-azatriene Fe(CO)3 complex was converted into the 2-substituted dehydropiperidinone 8, from which a piperidine alkaloid 1 (SS20846A) was synthesized in an enantiomerically pure form via successive reduction and removal of the protecting groups. Although the reduction of the ketone 3 proceeded with cis-selectivity even with a hindered reducing agent, the desired trans-alcohol 4 could be obtained by the reaction with sodium borohydride in the presence of cerium(III) chloride. The cis-selective reduction of 3 originates from the equatorial attack of a hydride on conformer A, in which the diene Fe(CO)3 moeity is axially oriented due to the severe steric hindrance with the p-methoxyphenyl (PMP) group on the nitrogen atom. However, the cerium salt reverses the stereoselectivity of the hydride reduction of 3.
• Asymmetric synthesis of alkaloid (−)-(2S,4S ) SS 20846 A and its C-4 epimer
  作者：Isabelle Ripoche、Jean-Louis Canet、Bettina Aboab、Jacques Gelas、Yves Troin

  DOI：10.1039/a804288h

  日期：——

  A diastereoselective intramolecular Mannich reaction using planar chiral iron dienal complexes is employed to prepare optically pure 2,4-disubstituted piperidines. This methodology is applied to the synthesis of natural alkaloids (–)-6 and (–)-7.