(R)-4-(trimethylsilylmethyl)pent-4-en-2-amine | 602275-87-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: (R)-4-(trimethylsilylmethyl)pent-4-en-2-amine
• 英文别名: (R)-1-methyl-3-(methyltrimethylsilane)-3-butenylamine；(2R)-4-(trimethylsilylmethyl)pent-4-en-2-amine
• CAS: 602275-87-6
• 化学式: C₉H₂₁NSi
• 分子量: 171.358
• InChiKey: YURWKZFHSQOSAH-SECBINFHSA-N

物化性质

• 沸点：
  43 °C(Press: 1 Torr)
• 密度：
  0.809±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-4-(trimethylsilylmethyl)pent-4-en-2-amine 在 4 A molecular sieve 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 (R)-4-Methyl-2-methylene-octahydro-quinolizine
  参考文献：
  名称：

  Cascade Iminium Ion Reactions for the Facile Synthesis of Quinolizidines. Concise Syntheses of (±)-Epilupinine and (−)-Epimyrtine

  摘要：

  Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids epilupinine and (-)-epimyrtine.

  DOI：

  10.1021/ol050544b
• 作为产物：
  描述：

  (4R)-4-amino-1-trimethylsilyl-2-(trimethylsilylmethyl)pentan-2-ol 在 盐酸 、 水 作用下， 以 乙醚 为溶剂， 以93%的产率得到(R)-4-(trimethylsilylmethyl)pent-4-en-2-amine
  参考文献：
  名称：

  轻松合成2-（2-氨基乙基）烯丙基硅烷的对映选择性合成，是用于哌啶合成的新合成子

  摘要：

  描述了通过将铈介导的三甲基甲硅烷基甲基氯化镁加到非外消旋手性β-氨基酯的酯基上来合成手性（2-取代的2-氨基乙基）烯丙基硅烷。

  DOI：

  10.1016/s0040-4039(03)01428-x

文献信息

• Iminium ion cascade reactions: stereoselective synthesis of quinolizidines and indolizidines
  作者：Shawn M. Amorde、Ivan T. Jewett、Stephen F. Martin

  DOI：10.1016/j.tet.2008.10.074

  日期：2009.4

  A novel iminium ion cascade reaction has been developed that allows for the stereoselective synthesis of a variety of substituted aza-fused bicycles. The combination of amino allylsilanes and aldehydes (or ketones) was used to synthesize a number of quinolizidines and indolizidines in a one-pot reaction sequence. This technology has been used to effect the facile syntheses of several indolizidine and

  已经开发了一种新型亚胺离子级联反应，可以立体选择性地合成各种取代的氮杂融合双环。氨基烯丙基硅烷和醛（或酮）的组合被用于在一锅反应序列中合成许多喹唑西啶和吲哚里西啶。该技术已被用于实现几种吲哚里西啶和喹诺西啶天然产物的简便合成，包括 (±)-epilupinine、(±)-tashiromine 和 (-)-epimyrtine。已经检查了底物范围，改变氨基烯丙基硅烷（伯、仲和共轭）和羰基化合物（醛和酮）的类型，以提供各种稠环结构。改变选择的组分允许在核心结构的不同位置包含合成有用的官能团。
• A new asymmetric synthesis of 2,6-cis-disubstituted 4-methylenepiperidines: total synthesis of (+)-alkaloid 241D and (+)-isosolenopsin A
  作者：Jérémy Monfray、Yvonne Gelas-Mialhe、Jean-Claude Gramain、Roland Remuson

  DOI：10.1016/j.tetasy.2005.01.018

  日期：2005.3

  A highly diastereoselective synthesis of 2,6-cis-disubstituted-4-methylenepiperidines based on a Mannich type intramolecular cyclization of an allylsilane on an iminium ion is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of two natural piperidine alkaloids: (+)-alkaloid 241 D and (+)-isosolenopsin A. (C) 2005 Elsevier Ltd. All rights reserved.
• A facile enantioselective synthesis of 2-(2-aminoethyl)allylsilanes, new synthons for piperidine synthesis
  作者：Jérémy Monfray、Yvonne Gelas-Mialhe、Jean-Claude Gramain、Roland Remuson

  DOI：10.1016/s0040-4039(03)01428-x

  日期：2003.7

  The synthesis of chiral (2-substituted-2-aminoethyl)allylsilanes by cerium mediated trimethylsilylmethylmagnesium chloride addition to the ester group of non racemic chiral β-aminoesters is described.

  描述了通过将铈介导的三甲基甲硅烷基甲基氯化镁加到非外消旋手性β-氨基酯的酯基上来合成手性（2-取代的2-氨基乙基）烯丙基硅烷。
• Cascade Iminium Ion Reactions for the Facile Synthesis of Quinolizidines. Concise Syntheses of (±)-Epilupinine and (−)-Epimyrtine
  作者：Shawn M. Amorde、Andrew S. Judd、Stephen F. Martin

  DOI：10.1021/ol050544b

  日期：2005.5.1

  Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids epilupinine and (-)-epimyrtine.