(+)-isosolenopsin A | 137038-58-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (+)-isosolenopsin A
• 英文别名: (2R,6S)-isosolenopsin A；2(R)-methyl-6(S)-undecylpiperidine；(2r,6s)-2-Methyl-6-undecylpiperidine
• CAS: 137038-58-5
• 化学式: C₁₇H₃₅N
• 分子量: 253.472
• InChiKey: AYJGABFBAYKWDX-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-isosolenopsin A 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (2R,6S)-(-)-isosolenopsin A hydrochloride
  参考文献：
  名称：

  Cross-Metathesis of Chiral N-tert-Butylsulfinyl Homoallylamines: Application to the Enantioselective Synthesis of Naturally Occurring 2,6-cis-Disubstituted Piperidines

  摘要：

  哌啶生物碱 (+)-二氢哌啶 (1)、(+)-异茄红素 (2a)、(+)-异茄红素 A (2b) 和 (2R,6R)-6-甲基哌啶酸 (3a) 盐酸盐的合成提出了手性 N-叔丁基亚磺酰高烯丙胺与甲基乙烯基酮的交叉复分解反应。

  DOI：

  10.1055/s-0028-1083535
• 作为产物：
  描述：

  (4R)-4-amino-1-trimethylsilyl-2-(trimethylsilylmethyl)pentan-2-ol 在 四氧化锇 、 sodium paraperiodate 、 三氟化硼乙醚 、 氢气 、 镍 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 47.0h， 生成 (+)-isosolenopsin A
  参考文献：
  名称：

  A new asymmetric synthesis of 2,6-cis-disubstituted 4-methylenepiperidines: total synthesis of (+)-alkaloid 241D and (+)-isosolenopsin A

  摘要：

  A highly diastereoselective synthesis of 2,6-cis-disubstituted-4-methylenepiperidines based on a Mannich type intramolecular cyclization of an allylsilane on an iminium ion is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of two natural piperidine alkaloids: (+)-alkaloid 241 D and (+)-isosolenopsin A. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.018

文献信息

• Synthesis of enantiomerically pure fire ant venom alkaloids: Solenopsins and isosolenopsins A, B and C
  作者：H. M. T. Bandara Herath、N. P. Dhammika Nanayakkara

  DOI：10.1002/jhet.5570450112

  日期：2008.1

  Concise and efficient methods for the synthesis of enantiomers of fire ant venom alkaloids solenopsin and isosolenopsin A, B, and C are described. These syntheses are based on diastereoselective electrophilic substitution of enatiomerically-pure α-lithiated 2-alkylpiperidine.

  描述了一种简单有效的合成火蚁毒生物碱slenoppsin和isosolenopsin A，B和C对映异构体的方法。这些合成基于对映体纯的α-锂化的2-烷基哌啶的非对映选择性亲电取代。
• Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
  作者：Ana Sirvent、Francisco Foubelo、Miguel Yus

  DOI：10.3390/molecules26216503

  日期：——

  functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the

  在加入官能化有机锂化合物的由5-氯-2-甲氧基-1-戊烯和6-氯-2-甲氧基-1-己烯衍生ñ -叔-butanesulfinyl醛亚胺亚胺和烯醇醚部分的随后的水解，分别以中等产率和非对映选择性产生不同的 δ- 和 ε-氨基酮衍生物。这些化合物在有机合成中的应用通过以立体选择性的方式制备 2-取代的 6-甲基哌啶来证明，其中包括天然生物碱 (+)- 和 (-)-isosolenopsin A。
• Cross-Metathesis of Chiral <i>N</i>-<i>tert</i>-Butylsulfinyl Homoallylamines: Application to the Enantioselective Synthesis of Naturally Occurring 2,6-<i>cis</i>-Disubstituted Piperidines
  作者：Francisco Foubelo、Miguel Yus、José González-Gómez

  DOI：10.1055/s-0028-1083535

  日期：——

  The synthesis of piperidine alkaloids (+)-dihydropinidine (1), (+)-isosolenopsin (2a), (+)-isosolenopsin A (2b), and (2R,6R)-6-methylpipecolic acid (3a) hydrochlorides, based on cross-metathesis of chiral N-tert-butylsulfinyl homoallylamines with methyl vinyl ketone, is presented.

  哌啶生物碱 (+)-二氢哌啶 (1)、(+)-异茄红素 (2a)、(+)-异茄红素 A (2b) 和 (2R,6R)-6-甲基哌啶酸 (3a) 盐酸盐的合成提出了手性 N-叔丁基亚磺酰高烯丙胺与甲基乙烯基酮的交叉复分解反应。
• Removal of the Pyridine Directing Group from α-Substituted<i>N</i>-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp³C–H Functionalization
  作者：Veerle Smout、Aldo Peschiulli、Stefan Verbeeck、Emily A. Mitchell、Wouter Herrebout、Patrick Bultinck、Christophe M. L. Vande Velde、Didier Berthelot、Lieven Meerpoel、Bert U. W. Maes

  DOI：10.1021/jo401521y

  日期：2013.10.4

  Two strategies, "hydrogenation-hydride reduction" and. "quaternization-hydride reduction", are reported, that make use of mild reaction conditions (room temperature) to efficiently remove the N-pyridin-2-yl directing group from a diverse set of C-2-substituted piperidines that were synthesized through directed Ru-catalyzed Sp(3) C-H functionalization. The deprotected products are obtained in moderate to good overall yields irrespective of the strategy followed, indicating that both methods are generally. equally effective. Only in the case of 2,6-disubstituted piperidines, could the "quaternization-hydride reduction" strategy not be used. The "hydrogenation-hydride reduction" protocol was successfully applied to trans- and cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine in a short synthetic route toward (+/-)-solenopsin A (trans diastereoisomer) and (+/-)-isosolenopsin A (cis diastereoisomer). The absolute configuration of the enantiomers of these fire: ant alkaloids could be determined via VCD spectroscopy.
• A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C
  作者：Stéphane Ciblat、Pascale Besse、Vassiliki Papastergiou、Henri Veschambre、Jean-Louis Canet、Yves Troin

  DOI：10.1016/s0957-4166(00)00162-2

  日期：2000.6

  A diastereospecific intramolecular Mannich-type reaction, involving enantiopure amine 4 and achiral aldehydes, is employed as the key step of an efficient total enantioselective synthesis of five piperidine alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.