6-phenyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 6-phenyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
• 英文别名: McN-4612-Z；rac-MCN-4612-Z；(6RS,10bSR)-hexahydro-6-phenylpyrrolo[2,1-a]isoquinoline；6-Phenyl-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline；(6R,10bS)-6-phenyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: KJHWRRVSXANANB-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-phenyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 (6R,10bR)-6-phenyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline;hydrochloride
  参考文献：
  名称：

  Stereochemistry of intramolecular amidoalkylation reactions in the synthesis of polycyclic isoquinoline derivatives

  摘要：

  DOI：

  10.1021/jo00173a053
• 作为产物：
  描述：

  1,5,6,10bβ-tetrahydro-6α-phenylpyrrolo<2,1-a>isoquinolin-3(2H)-one 在 盐酸 、 硼烷 作用下， 生成 6-phenyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
  参考文献：
  名称：

  Stereochemistry of intramolecular amidoalkylation reactions in the synthesis of polycyclic isoquinoline derivatives

  摘要：

  DOI：

  10.1021/jo00173a053

文献信息

• One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds
  作者：Qiao Song、Yan Liu、Linlin Cai、Xinyu Cao、Shan Qian、Zhouyu Wang

  DOI：10.1016/j.cclet.2021.01.018

  日期：2021.5

  Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the

  融合的吲哚并立定和喹喔啉是多种天然产物和重要药理化合物的重要骨架。公开了一种从酰胺到稠合的吲哚并咪唑和喹喔啉的一锅串联路线。该方法在温和条件下进行，显示出对官能团的良好耐受性。它也容易按比例放大至克级，并且可以平滑地应用于生物碱的全合成，例如（±）-crispine A，（±）-xylopinine，（±）-desbromoarborescidine A，（±）-harmicine和其他生物活性物质。
• TMSOTf mediated ‘5/6-<i>endo-dig</i>’ reductive hydroamination for the stereoselective synthesis of pyrrolidine and piperidine derivatives
  作者：Santosh J. Gharpure、Dharmendra S. Vishwakarma、Raj K. Patel

  DOI：10.1039/c9cc03127h

  日期：——

  A TMSOTf mediated 5/6-endo-dig reductive hydroamination cascade on internal alkynylamines gave expedient, stereoselective access to pyrrolidine and piperidine derivatives. We also demonstrate that a protecting group on nitrogen has a profound effect on the reactivity as well as diastereoselectivity of the reductive hydroamination cascade.

  在内部炔基胺上进行TMSOTf介导的5 / 6-内切还原还原氨化级联反应可方便地，立体选择性地获得吡咯烷和哌啶衍生物。我们还证明，氮上的保护基对还原性水胺化级联反应的反应性和非对映选择性具有深远的影响。
• A convenient asymmetric synthesis of pyrrolo[2,1-a]isoquinolines
  作者：A.I. Meyers、Joseph Guiles

  DOI：10.1016/0040-4039(90)80155-f

  日期：1990.1

  A four-step synthesis of optically pure 6α-phenyl pyrroloisoquinolines from chiral formamidines has been accomplished.

  由手性甲am完成了光学纯的6α-苯基吡咯并异喹啉的四步合成。
• Diastereoselective Allylation of 3,4-Dihydro-4-phenylisoquinoline. Convenient Methods for the Preparation of<i>cis</i>- and<i>trans</i>-1-Allyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
  作者：Ayako Taketoshi、Naoya Hosoda、Yoshitaka Yamaguchi、Masatoshi Asami

  DOI：10.1246/bcsj.80.2418

  日期：2007.12.15

  Diastereoselective allylation of 3,4-dihydro-4-phenylisoquinoline by several allylating reagents was examined. Reactions using allyltin or allylsilane in the presence of alkyl chloroformate and a catalytic amount of trimethylsilyl triflate gave trans-1-allyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline with moderate diastereoselectivity. In contrast, cis-1-allyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline was obtained predominantly in the reactions using allyllithium, triallylborane, allylzinc bromide, and diallylzinc. cis-1-Allyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline was transformed to (6S∗,10bR∗)-hexahydro-6-phenylpyrrolo[2,1-a]isoquinoline, a potential antidepressant agent, in five steps.

  研究了几种烯丙基化试剂对 3,4-二氢-4-苯基异喹啉的非对映选择性烯丙基化。在氯甲酸烷基酯和催化量的三氟甲磺酸三甲基甲硅烷基酯存在下，使用烯丙基锡或烯丙基硅烷进行反应，得到具有中等非对映选择性的反式-1-烯丙基-4-苯基-1,2,3,4-四氢异喹啉。相比之下，顺-1-烯丙基-4-苯基-1,2,3,4-四氢异喹啉主要是在使用烯丙基锂、三烯丙基硼烷、烯丙基溴化锌和二烯丙基锌的反应中获得的。 cis-1-烯丙基-4-苯基-1,2,3,4-四氢异喹啉被转化为 (6S*,10bR*)-六氢-6-苯基吡咯并[2,1-a]异喹啉，一种潜在的抗抑郁剂，五个步骤。
• Stereoselective reaction for hexahydro-6-arylpyrrolo(2,1-A) isoquinolines
  申请人：McNeilab, Inc.

  公开号：US04837328A1

  公开（公告）日：1989-06-06

  A diastereoselective process for known antidepressive compounds (I) via reduction of the corresponding alcohol (VII): ##STR1## whereby the product mixture of diastereomers is surprisingly and unexpectedly rich in the content of the trans configuration (II) over the cis configuration (III) as defined in the following formulae: ##STR2## The preferred reaction conditions include use of a borane complex as the reducing agent and an acidic solvent such as trifluoroacetic acid.

  一种通过还原相应醇（VII）对已知抗抑郁化合物（I）进行对映选择性过程的方法：##STR1##其中，对映异构体的产物混合物出乎意料地丰富于顺式构象（II）的含量，而非顺式构象（III），如下公式所示：##STR2##首选的反应条件包括使用硼烷复合物作为还原剂和三氟乙酸等酸性溶剂。