2-(Trimethylsilyl)pyrrolidine | 174363-70-3

• 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: 2-(Trimethylsilyl)pyrrolidine
• 英文别名: 2-Trimethylsilylpyrollidine；trimethyl(pyrrolidin-2-yl)silane
• CAS: 174363-70-3
• 化学式: C₇H₁₇NSi
• mdl: MFCD19217257
• 分子量: 143.304
• InChiKey: KQRWBDURMARJQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  9
• 可旋转键数：
  1
• 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：

  2-(Trimethylsilyl)pyrrolidine 在 Lindlar's catalyst 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 25.0 ℃ 、241.32 kPa 条件下， 反应 11.0h， 生成 1-(5-Hydroxypent-3-enyl)-2-(trimethylsilyl)pyrrolidine
  参考文献：
  名称：

  Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine

  摘要：

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.

  DOI：

  10.1039/p19960000219
• 作为产物：
  描述：

  1-Boc-2-三甲基锡吡咯烷 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 2-(Trimethylsilyl)pyrrolidine
  参考文献：
  名称：

  具有碳-碳多重键的“N-酰基胺离子池”的环加成

  摘要：

  发现由 α-甲硅烷基氨基甲酸酯生成的 N-Acyliminium 离子池与各种烯烃和炔烃反应生成相应的环加合物。与苯乙烯衍生物的反应导致形成大量聚合产物。然而，微混合的使用导致环加合物产率的显着增加，但以聚合物为代价。机理研究表明，对于烷基取代的烯烃，协调机制似乎最有可能，而对于芳基取代的烯烃，逐步机制似乎是合理的。

  DOI：

  10.1246/bcsj.78.1206

文献信息

• Catalyst for the polymerization of alpha-olefins containing substituted
  申请人：Montell North America Inc.

  公开号：US06130180A1

  公开（公告）日：2000-10-10

  An aminosilane of the formula: ##STR1## where R.sub.1 is a linear or branched C.sub.1-22 alkyl or C.sub.3-22 cycloalkyl, which may be substituted with at least one halogen atom; R.sub.2 is a bis(linear or branched C.sub.1-22 alkyl or C.sub.3-22 cycloalkyl)amino, a substituted piperidinyl, a substituted pyrrolidinyl, decahydroquinolinyl, 1,2,3,4-tetrahydroquinolinyl or 1,2,3,4-tetrahydroisoquinolinyl, with the substituent selected from the group consisting of C.sub.1-8 alkyl, pheny. C.sub.1-8 linear or branched alkylsubstituted phenyl and trimethylsilyl, with the proviso that when the substituent is C.sub.1-8 alkyl, there must be at least two such substituent groups present and R.sub.1 must contain halogen; and R.sub.3 is a linear or branched C.sub.1-8 alkyl or C.sub.3-8 cycloalkyl. The aminosilane may be reacted with an aluminum-alkyl compound and a solid component comprising a titanium compound having at least one titanium-halogen bond and an electron donor, both supported on an activated anhydrous magnesium dihalide, to form a catalyst for polymerization of olefins.

  一种氨基硅烷的化学式：##STR1## 其中R.sub.1是线性或支链的C.sub.1-22烷基或C.sub.3-22环烷基，可以被至少一个卤素原子取代; R.sub.2是双(线性或支链的C.sub.1-22烷基或C.sub.3-22环烷基)氨基，取代的哌啶基，取代的吡咯烷基，十氢萘基，1,2,3,4-四氢萘基或1,2,3,4-四氢异喹啉基，取代基被选择为由C.sub.1-8烷基，苯基，C.sub.1-8线性或支链烷基取代的苯基和三甲基硅基组成的群，前提是当取代基是C.sub.1-8烷基时，必须至少有两个这样的取代基存在，并且R.sub.1必须含有卤素; R.sub.3是线性或支链的C.sub.1-8烷基或C.sub.3-8环烷基。该氨基硅烷可以与铝烷化合物和固体组分反应，该固体组分包括至少具有一种钛-卤素键和一个电子给体的钛化合物，两者都支持在活性无水二卤化镁上，以形成用于聚烯烃聚合的催化剂。
• Stuhlmann; Kaufmann, Advanced Synthesis and Catalysis, 1999, vol. 341, # 5, p. 455 - 460
  作者：Stuhlmann、Kaufmann

  DOI：——

  日期：——
• Ag(I)F as one electron oxidant for promoting sequential double desilylation : An ideal approach to non-stabilized azomethine ylides for the rapid construction of 1-azabicyclo (m:3:0) alkanes
  作者：Ganesh Pandey、G. Lakshmaiah

  DOI：10.1016/s0040-4039(00)74110-4

  日期：1993.7

  A novel methodology for effecting sequential double desilylation by Ag(I)F for the generation of non-stabilized azomethine ylide and its application for the synthesis of 1-azabicyclo(m.3.0) alkane systems are described.
• Pandey, Ganesh; Lakshmaiah; Gadre, Smita R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 91 - 98
  作者：Pandey, Ganesh、Lakshmaiah、Gadre, Smita R.

  DOI：——

  日期：——
• Synthesis and evaluation of 1-deoxy-8-epi-castanospermine, 1-deoxy-8-hydroxymethyl castanospermine, and (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol
  作者：Ganesh Pandey、Shrinivas G. Dumbre、Sujit Pal、M. Islam Khan、M. Shabab

  DOI：10.1016/j.tet.2007.03.085

  日期：2007.5

  A short, versatile, and enantioselective synthesis of 1-deoxy-8-epi-castanospermine (5), 1-deoxy-8-hydroxymethyl castanospermine (6), and (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol (7) is achieved from a common template 12. The key step utilized is PET provoked amine radical cyclization of 11 to 12 in excellent diastereoselectivity. The exocyclic double bond at C-8 of the template is functionalized to obtain 5-7 as exclusive diastereomers. 1-Deoxy-8-epi-castanospermine exhibited inhibition of alpha- and beta-galactosidase and beta-glucosidase. Compounds 6 and 7 were found to be weak inhibitors of beta-glucosidase. (C) 2007 Elsevier Ltd. All rights reserved.