cis-2-butyl-5-heptylpyrrolidine | 116558-83-9

• 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: cis-2-butyl-5-heptylpyrrolidine
• 英文别名: (2S,5R)-2-butyl-5-heptylpyrrolidine
• CAS: 116558-83-9
• 化学式: C₁₅H₃₁N
• 分子量: 225.418
• InChiKey: FIXZYWKWWCBXRZ-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  9
• 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：

  cis-2-butyl-5-heptylpyrrolidine 、 N-氯代丁二酰亚胺 生成 2-butyl-5-heptyl-5-pyrroline
  参考文献：
  名称：

  GESSNER, WIESLAW;TAKAHASHI, KIMIO;BROSSI, ARNOLD;KOWALSKI, MAREK;KAIINER,+, HELV. CHIM. ACTA., 70,(1987) N 8, 2003-2010

  摘要：

  DOI：
• 作为产物：
  描述：

  2-壬酮 在 Rh/Al₂O₃ 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 cis-2-butyl-5-heptylpyrrolidine
  参考文献：
  名称：

  Miyashita, Masaaki; Awen, Bahlul Z. E.; Yoshikoshi, Akira, Chemistry Letters, 1990, # 2, p. 239 - 242

  摘要：

  DOI：

文献信息

• Diastereo- and enantioselective syntheses of (−)-coniine, (−)-solenopsin A, (−)-solenopsis fugaz venom and (−)-xenovenine via deoxygenative decarboxylation of 2-carbonylsultam-substituted n-hydroxy-piperidines and -pyrrolidines
  作者：Wolfgang Oppolzer、Christian G. Bochet、Eric Merifield

  DOI：10.1016/0040-4039(94)88213-4

  日期：1994.9

  Heating cyclic 2-carbonylsultam-substituted N-hydroxylamines 4 with NaH yields sultam auxiliary 8 and imines 10, which are trapped in situ either by i-Bu2AlH or organocerium reagents to give enantiomerically pure 2-mono- or trans-2,6(2,5)-disubstituted piperidines (pyrrolidines) 11 or 12.

  加热循环2 carbonylsultam取代Ñ -hydroxylamines 4用NaH产量磺内酰胺辅助8个亚胺10，其被捕获在原位由任何我-Bu 2的AlH或有机铈试剂，得到对映体纯2单-或反式-2,6- （2，5）-二取代的哌啶（吡咯烷）11或12。
• Asymmetric Synthesis of Polyfunctionalized Pyrrolidines from Sulfinimine-Derived Pyrrolidine 2-Phosphonates. Synthesis of Pyrrolidine 225C
  作者：Franklin A. Davis、He Xu、Yongzhong Wu、Junyi Zhang

  DOI：10.1021/ol060521c

  日期：2006.5.1

  [reaction: see text] The Horner-Wadsworth-Emmons reaction of aldehydes with sulfinimine-derived 3-oxo pyrrolidine phosphonates represents a new method for the asymmetric synthesis of ring-functionalized cis-2,5-disubstituted 3-oxo pyrrolidines.

  [反应：见正文]醛与亚氨嘧啶衍生的3-氧代吡咯烷膦酸酯的醛的Horner-Wadsworth-Emmons反应代表了一种不对称合成环官能化的顺式2,5-二取代的3-氧代吡咯烷的新方法。
• Synthesis of (�)-trans-2,5-Dialkylpyrrolidines from theLukes-?orm Dilactam: Efficient Preparation of (�)-trans-2-Butyl-5-heptylpyrrolidine and Analogs Present in Ant Venoms
  作者：Wieslaw Gessner、Kimio Takahashi、Arnold Brossi、Marek Kowalski、Michael A. Kaliner

  DOI：10.1002/hlca.19870700805

  日期：1987.12.16

  A 7-step synthesis of (±)-trans-2-butyl-5-heptylpyrrolidine (14) from the Lukes-Šorm dilactam 1 was accomplished in 6% overall yield without counting for a reconversion of cis-isomer 13 into trans-isomer 14 which was also accomplished. Reduction of pyrroline 12, the precursor of 14, with NaBH4 afforded a 1:1 mixture of cis-isomer 13 and trans-isomer 14 separated by chromatography. Reductive N-methylation

  的（±）A 7步合成-反式-2-丁基-5- heptylpyrrolidine（14从）卢克什-SORM双内酰胺1在6％的总收率完成而不计数为一个再变换的顺式-异构体13为反式-异构体14也完成了。用NaBH 4还原14的前体吡咯啉12，得到通过色谱法分离的1：1的顺式异构体13和反式异构体14混合物。14的还原性N-甲基化得到另一种蚂蚁生物碱N-甲基类似物15。合成途径14延长到类似物的类似合成23 - 25和代表用于合成反式-2,5- diakyl取代的吡咯烷。报道了筛选几种对血管通透性有影响的化合物的结果。
• (2R-trans)-2-Butyl-5-heptylpyrrolidine as a Potent Sigma Receptor Ligand Produced by Streptomyces longispororuber.
  作者：KAZUO KUMAGAI、KAZUSHIGE SHONO、HIROSHI NAKAYAMA、YUKIHIRO OHNO、IKUTARO SAJI

  DOI：10.7164/antibiotics.53.467

  日期：——

  A potent sigma (σ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber #525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for σ receptors. The IC50 values toward σ1, σ2 and dopamine D2 receptors were 2.0, 22.7 and more than 40, 000 nM, respectively. Its (2S-trans)- and (±)-cis-isomers, both synthesized, were also found to be high affinity σ ligands.

  从长孢子链霉菌（Streptomyces longispororuber #525）的培养液中分离出一种强效的σ（sigma）受体配体。通过光谱和化学研究，确定该活性化合物为 (2R-trans)-2- 丁基-5-庚基吡咯烷。该化合物对 σ 受体具有高亲和力和选择性。对 σ1、σ2 和多巴胺 D2 受体的 IC50 值分别为 2.0、22.7 和超过 40,000 nM。合成的(2S-反式)-和(±)-顺式异构体也被发现是高亲和力的σ配体。
• Total Synthesis of Pyrrolidine and Piperidine Natural Products via TMSOTf-Mediated “5/6-<i>endo-dig</i>” Reductive Hydroamination of Enynyl Amines
  作者：Santosh J. Gharpure、Raj K. Patel、Krishna S. Gupta

  DOI：10.1021/acs.orglett.3c02115

  日期：2023.8.11

  acid-mediated 5/6-endo-dig reductive hydroamination cascade of enynyl amines. The brevity of the developed strategy allowed for the collective stereoselective total synthesis of various alkaloids, including (±)-pyrrolidine cis-225H, (±)-epi-197B, (±)-epi-225C, the family of (+)-solenopsins and (+)-isosolenopsins, and the formal synthesis of (±)-bgugaine and (+)-azimic acid.

  带有疏水链的吡咯烷和哌啶的立体选择性合成已经通过烯炔胺的无金属、路易斯酸介导的5/6-内位还原氢胺化级联实现。所开发策略的简洁性允许集体立体选择性全合成各种生物碱，包括(±)-吡咯烷顺式-225H、(±)- epi -197B、(±)- epi -225C、(+)-家族Solenopins 和 (+)-isosolenopsins，以及 (±)-bgugaine 和 (+)-azimic Acid 的正式合成。