solenopsin B | 32778-77-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: solenopsin B
• 英文别名: rel-(2R,6R)-2-Methyl-6-tridecylpiperidine；(2R,6R)-2-methyl-6-tridecylpiperidine
• CAS: 32778-77-1
• 化学式: C₁₉H₃₉N
• 分子量: 281.525
• InChiKey: AJAXYTHTWGIEHL-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  20
• 可旋转键数：
  12
• 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

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  solenopsin B 、 对甲苯磺酰氯 生成 N-tosyl solenopsin B
  参考文献：
  名称：

  Pd(O) promoted transformation of N-tosyl-2-(1,3-butadienyl)-aziridine into N-tosyl-2-vinyl-3-pyrroline

  摘要：

  DOI：

  10.1016/s0040-4039(00)61948-2
• 作为产物：
  描述：

  3-氧代十六烷酸甲酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 二异丁基铝-2,6-二-叔丁基-4-羟基甲苯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 78.83h， 生成 solenopsin B
  参考文献：
  名称：

  Enantioselective construction of heterocycles. Synthesis of (R,R)-solenopsin B

  摘要：

  DOI：

  10.1021/jo00248a013

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。
• Asymmetric synthesis of solenopsins A, B and C
  作者：Guy Solladié、Nathalie Huser

  DOI：10.1002/recl.19951140405

  日期：——

  Solenopsins A, B and C have been synthesized in enantiomerically pure forms from the corresponding anti-1,5-diols which have been obtained from glutaric anhydride by an asymmetric synthesis induced by chiral sulfoxides.

  Solenopsins A，B和C由对映体纯形式由相应的抗-1,5-二醇合成，该抗-1,5-二醇是由手性亚砜诱导的不对称合成从戊二酸酐获得的。
• Synthesis of solenopsin B via stereoselective reduction of Bicyclic N,O-ketals
  作者：Hiyoshizo Kotsuki、Toshio Kusumi、Mase Inoue、Yasuyuki Ushio、Masamitsu Ochi

  DOI：10.1016/s0040-4039(00)79891-1

  日期：1991.8

  A new enantioselective total synthesis of (−)-solenopsin B was described starting from L-glutamic acid as an optically active natural source, in which stereoselective reduction of bicyclic N,O-ketals with DIBALH was used as the key reaction step.

  从L-谷氨酸作为旋光性天然来源开始，描述了一种新的对映体全合成（-）-solenopsin B，其中以DIBALH立体选择性还原双环N，O-缩酮为关键反应步骤。
• Organoaluminum-promoted Beckmann rearrangement of oxime sulfonates
  作者：Keiji Maruoka、Tohru Miyazaki、Mamoru Ando、Yasushi Matsumura、Soichi Sakane、Kazunobu Hattori、Hisashi Yamamoto

  DOI：10.1021/ja00347a052

  日期：1983.5
• Absolute configuration of the solenopsins, venom alkaloids of the fire ants.
  作者：S. Leclercq、I. Thirionet、F. Broeders、D. Daloze、R. Vander Meer、J.C. Braekman

  DOI：10.1016/s0040-4020(01)85567-8

  日期：1994.1

  An effective and practical procedure has been developed that allows the assignment of the absolute configuration of solenopsins from diverse origins using only small amounts of material. The method is based on the transformation of the natural secondary amines into diastereoisomeric amides by reaction with (R)-2-methoxy-2-phenyl-2-(trifluoromethyl)acetic acid chloride (MTPA-Cl), followed by comparison of their chromatographic behaviour with those of standards of established absolute configuration, This procedure has been applied to three samples of ants: Solenopsis geminata workers, S. invicta workers and S. invicta alates. It has been found that the absolute configuration of the trans alkaloids is always (2R,6R) while that of the cis alkaloids is (2R,6S). Moreover, a new synthesis of enantiomerically pure solenopsin A (4) and isosolenopsin A (3) starting from L-alanine is presented.