1-苄氧羰基-4-苯基-1,2,3,6-四氢吡啶 | 161609-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苄氧羰基-4-苯基-1,2,3,6-四氢吡啶
• 英文名称: benzyl 4-phenyl-3,6-dihydropyridine-1(2H)-carboxylate
• 英文别名: 1-Benzyloxycarbonyl-4-phenyl-1,2,3,6-tetrahydropyridine；benzyl 4-phenyl-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 161609-91-2
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: VDECWNPIZYWOOC-UHFFFAOYSA-N

物化性质

• 沸点：
  442.7±45.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄氧羰基-4-苯基-1,2,3,6-四氢吡啶 在 palladium on activated charcoal 、 四氧化锇 sodium tetrahydroborate 、 N-甲基吲哚酮 、 jones reagent 、 次氯酸叔丁酯 、 三氟化硼乙醚 、 氢气 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 62.84h， 生成 (±)-coerulescine
  参考文献：
  名称：

  Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

  摘要：

  A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.015
• 作为产物：
  描述：

  4-羟基-1-哌啶甲酸苄酯 在 jones reagent 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 1-苄氧羰基-4-苯基-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

  摘要：

  A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.015

文献信息

• Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chiral Alkoxyamines as Precatalysts: Catalyst Structure, Active Species, and Substrate Scope
  作者：Keiichi Murakami、Yusuke Sasano、Masaki Tomizawa、Masatoshi Shibuya、Eunsang Kwon、Yoshiharu Iwabuchi

  DOI：10.1021/ja509766f

  日期：2014.12.17

  The development and characterization of enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols using chiral alkoxyamines as precatalysts are described. A number of chiral alkoxyamines have been synthesized, and their structure-enantioselectivity correlation study in OKR has led us to identify a promising precatalyst, namely, 7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane

  描述了使用手性烷氧基胺作为预催化剂的外消旋仲醇的对映选择性有机催化氧化动力学拆分 (OKR) 的开发和表征。已经合成了许多手性烷氧基胺，它们在 OKR 中的结构-对映选择性相关性研究使我们确定了一种有前途的前催化剂，即 7-苄基-3-正丁基-4-氧杂-5-氮杂高金刚烷，它提供了各种手性脂肪族仲醇（ee 高达 >99%，k(rel) 高达 296）。在一项机理研究中，含氯氧铵物种被确定为烷氧基胺预催化剂原位生成的活性物种，并且发现氯原子对于高反应性和对映选择性至关重要。
• Catalytic Friedel‐Crafts Reactions on Saturated Heterocycles and Small Rings for sp ³ ‐sp ² Coupling of Medicinally Relevant Fragments
  作者：Rosemary A. Croft、Maryne A. J. Dubois、Alexander J. Boddy、Camille Denis、Anna Lazaridou、Anne Sophie Voisin‐Chiret、Ronan Bureau、Chulho Choi、James J. Mousseau、James A. Bull

  DOI：10.1002/ejoc.201900498

  日期：2019.9

  A systematic comparison of Lewis acid catalysts [Ca(II), Li(I) and Fe(III)] is presented for catalytic Friedel–Crafts reactions using alcohols on 4‐, 5‐, and 6‐membered oxygen and nitrogen heterocycles and cyclobutanes, forming gem‐diaryl quaternary centers.

  路易斯酸催化剂[Ca（II），Li（I）和Fe（III）]的系统比较被提出用于使用醇在4、5和6元氧和氮杂环和环丁烷上进行的催化Friedel-Crafts反应，形成宝石-二芳基四元中心。
• Aryl substituted heterocycles
  申请人：Zeneca Limited

  公开号：US05654299A1

  公开（公告）日：1997-08-05

  The present invention concerns the novel use of aryl substituted heterocycles of formula I, set out below, which antagonize the pharmacological actions of one of ent endogenous neuropeptide tachykinins an the neurokinin 2 (NK2) receptor making them useful whenever such antagonism is desired, such as in the treatment of asthma and related conditions. The invention also provides pharmaceutical compositions containing the aryl substituted heterocycles for use in such treatment. Certain novel aryl substituted heterocycles of formula I and novel intermediates for their manufacture are also provided. ##STR1##

  本发明涉及下面列出的式I的芳基取代杂环化合物的新用途，这些化合物拮抗一种内源性神经肽激肽素和神经激肽2（NK2）受体的药理作用，使其在需要这种拮抗作用的情况下非常有用，例如在治疗哮喘和相关疾病时。该发明还提供了含有这些芳基取代杂环化合物的药物组合物，用于这种治疗。还提供了某些新型的式I的芳基取代杂环化合物以及用于它们制备的新型中间体。
• Direct C–H Allylation of <i>N</i>-Acyl/Sulfonyl Tetrahydroisoquinolines and Analogues
  作者：Changcun Yan、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.5b03042

  日期：2015.11.20

  A highly efficient direct C–H allylation reaction at the α position of N-acyl/sulfonyl tetrahydroisoquinolines under mild conditions was developed. The reaction was also suitable for allylation of other protected nitrogen-containing heterocycles. Several interesting transformations of the products into valuable synthetic intermediates are featured with the successful total synthesis of (±)-crispine

  在温和条件下，开发了在N-酰基/磺酰基四氢异喹啉的α位上高效的直接CH烯丙基化反应。该反应也适合于其他保护的含氮杂环的烯丙基化。（±）-crispine A的成功全合成成功地将产品有趣地转化为有价值的合成中间体。
• A versatile synthesis of 4-aryl tetrahydropyridines via palladium mediated Suzuki cross-coupling with cyclic vinyl boronates
  作者：Paul R Eastwood

  DOI：10.1016/s0040-4039(00)00447-0

  日期：2000.5

  A simple preparation of cyclic vinyl boronates derived from the vinyl triflates of N-protected tetrahydropyridines is described. Suzuki coupling of the boronates with aryl bromides, iodides and triflates proceeds in good yield to give 4-aryl tetrahydropyridines.

  描述了衍生自N-保护的四氢吡啶的乙烯基三氟甲磺酸酯的环状硼酸乙烯基酯的简单制备。硼酸酯与芳基溴化物，碘化物和三氟甲磺酸酯的Suzuki偶联以良好的收率进行，得到4-芳基四氢吡啶。