2-(三甲基硅烷基)哌啶 | 174363-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-(三甲基硅烷基)哌啶
• 中文别名: 3-吡啶甲磺酸,5,5-1,4-亚苯基二亚氨基(6-氟-1,3,5-三嗪-4,2-二基)亚氨基(6-硫代-3,1-亚苯基)偶氮二1-乙基-1,2-二氢-6-羟基-4-甲基-2-羰基-,盐钠
• 英文名称: 2-(trimethylsilyl)piperidine
• 英文别名: 2-Trimethylsilylpiperidine；trimethyl(piperidin-2-yl)silane
• CAS: 174363-71-4
• 化学式: C₈H₁₉NSi
• 分子量: 157.331
• InChiKey: WVFLUUDVJHXQDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  10
• 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-(三甲基硅烷基)哌啶 在 Lindlar's catalyst 四氯化碳 、 sodium hydroxide 、 sodium tetrahydroborate 、 二甲基硫 、 萘-1,4-二腈 、 氢气 、 potassium carbonate 、 臭氧 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， -78.0~25.0 ℃ 、241.32 kPa 条件下， 反应 27.5h， 生成 1-表羽扇豆碱
  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-哌啶 在 四甲基乙二胺 、 仲丁基锂 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-(三甲基硅烷基)哌啶
  参考文献：
  名称：

  Pandey, Ganesh; Lakshmaiah; Gadre, Smita R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 91 - 98

  摘要：

  DOI：

文献信息

• Synthesis of polyfunctional quinolizidine alkaloids: development towards selective glycosidase inhibitors
  作者：Ganesh Pandey、Debasish Grahacharya、K. S. Shashidhara、M. Islam Khan、Vedavati G. Puranik

  DOI：10.1039/b907007a

  日期：——

  A highly divergent route to a variety of quinolizidine alkaloids is described. The enantiomeric precursors 22a and 22b utilized for the synthesis of these alkaloids were constructed stereospecifically from the PET cyclization of the corresponding acetylene tethered α-trimethylsilyl amine moieties 21a and 21b, respectively, both of which were synthesised from D-ribose. The polyhydroxy quinolizidine alkaloid 7 was found to be a selective inhibitor of α-galactosidase with Ki 83.9 μM. The amine analogs 18, 12 and 10 are found to be selective and potent inhibitors of α-glucosidase with Ki 28, 120 and 140 μM, respectively.

  本文描述了一种高度不同的喹嗪生物碱合成路线。用于合成这些生物碱的对映体前体 22a 和 22b，是分别从相应的乙炔系α-三甲基硅胺分子 21a 和 21b 的 PET 环化中立体定向生成的，这两个分子都是从 D-核糖合成的。研究发现，多羟基喹嗪生物碱 7 是 α-半乳糖苷酶的选择性抑制剂，Ki 为 83.9 μM。发现胺类似物 18、12 和 10 是 α-葡萄糖苷酶的选择性强效抑制剂，Ki 分别为 28、120 和 140 μM。
• 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。
• Exploratory Synthetic Studies of the α-Methoxylation of Amides <i>via</i> Cuprous Ion-Promoted Decomposition of <i>o</i>-Diazobenzamides
  作者：Gyoonhee Han、Matthew G. LaPorte、Mathias C. McIntosh、Steven M. Weinreb、Masood Parvez

  DOI：10.1021/jo961529a

  日期：1996.1.1

  A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1,5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting alpha-amidyl radical. The transformation produces alpha-methoxybenzamides 15 in good yields. An attempt was made to apply this oxidation method to a total synthesis of the alkaloid (-)-anisomycin (16). Scalemic o-aminobenzamide pyrrolidine derivatives 18a/18b underwent oxidation to give a-methoxylated amide substrates 19a/ 19b, respectively, in good yields. However, alkylation of the N-acyliminium intermediate 20 with (p-methoxybenzyl)magnesium chloride gave the undesired anti-compounds 22a/22b as the major products. The amide oxidation exhibits good regioselectivity with many unsymmetrical 2-substituted piperidine and pyrrolidine systems. In general, it appears that the larger the C-2 substituent, the greater the methylene/methine H-atom abstraction ratio. A mechanistic rationale for this selectivity is suggested based upon amide rotamer populations. An extension of this methodology can be used to conduct two sequential amide oxidations using readily prepared 2-amino-6-nitrobenzamides such as 68 and 69.
• 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.
• Gall, Erwan Le; Hurvois, Jean-Pierre; Sinbandhit, Sourisak, European Journal of Organic Chemistry, 1999, # 10, p. 2645 - 2654
  作者：Gall, Erwan Le、Hurvois, Jean-Pierre、Sinbandhit, Sourisak

  DOI：——

  日期：——