((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine | 192655-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine
• CAS: 192655-92-8
• 化学式: C₁₄H₂₁NSi
• 分子量: 231.413
• InChiKey: ABHZSZUWERHZSN-CYBMUJFWSA-N

物化性质

• 沸点：
  272.7±23.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  ((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine 在 吡啶 、 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 生成 ethyl [(E,5R)-5-[[(1R)-1-phenylethyl]-(3-trimethylsilylprop-2-ynyl)amino]hex-2-enyl] carbonate
  参考文献：
  名称：

  钛（II）介导的分子内环化反应从氨基酸衍生物立体选择性合成旋光取代的哌啶和吡咯烷

  摘要：

  开发了一种多功能的高产合成的光学活性取代的哌啶和吡咯烷，该衍生物是利用钛（II）介导的双不饱和碳酸酯的分子内环化反应从氨基酸衍生物合成的。

  DOI：

  10.1016/s0040-4039(97)10261-1
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 、 R(+)-alpha-甲基苄胺 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 生成 ((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine
  参考文献：
  名称：

  Reactive Dications:  The Superacid-Catalyzed Reactions of Alkynes Bearing Adjacent N-Heterocycles or Amine Groups

  摘要：

  A variety of aminoalkynes and related heterocycles are reacted in the Bronsted superacid CF3SO3H (triflic acid), and products are obtained in generally good yields (69-99%) from Friedel-Crafts-type reactions. The reactions are consistent with the formation of novel dicationic intermediates having a vinyl cationic site and an adjacent protonated N-heterocycle or ammonium cation.

  DOI：

  10.1021/jo040218u

文献信息

• A Facile Preparation of <i>e</i><i>xo</i>-Cyclic Conjugated Dienes Fused to Lactams or Lactones via Intramolecular Coupling of Acetylenes and Their Behavior in Diels−Alder Reactions
  作者：Hirokazu Urabe、Ryota Nakajima、Fumie Sato

  DOI：10.1021/ol0065221

  日期：2000.11.1

  [reaction: see text] Treatment of bis-acetylenic amides or esters 3 with (eta(2)-propene)Ti(O-i-Pr)(2) generates functionalized titanacyclopentadienes which, upon hydrolytic workup, give exo, exo-cyclic conjugated dienes 4 in good yields. Some regio- and stereochemical aspects of their Diels-Alder reaction with dienophiles are also disclosed.

  [反应：参见正文]用（eta（2）-丙烯）Ti（Oi-Pr）（2）处理双炔酰胺或酯3生成官能化的钛环戊二烯，经水解后，可得到外，外环共轭二烯4个单产好。还公开了它们与亲双烯体的Diels-Alder反应的一些区域和立体化学方面。
• Efficient and Practical Method for Synthesizing N-Heterocyclic Compounds Using Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Ti(O-<i>i</i>-Pr)₄/2<i>i</i>-PrMgX Reagent. Synthesis of Quinolones, Pyrroles, Indoles, and Optically Active N-Heterocycles Including Allopumiliotoxin Alkaloid 267A
  作者：Sentaro Okamoto、Masayuki Iwakubo、Katsushige Kobayashi、Fumie Sato

  DOI：10.1021/ja970810j

  日期：1997.7.1

  Treatment of N-(2- or 3-alkynyl)amino esters with a low-valent titanium reagent diisopropoxy(eta(2)-propene)titanium (1), generated in situ by the reaction of Ti(O-i-Pr)(4) and 2i-PrMgCl, resulted in an intramolecular nucleophilic acyl substitution (INAS) reaction to afford alpha-alkylidene-pyrrolidinones or -piperidinones. Thus, treatment of N-propargyl-anthranilates 5, -indole-2-carboxylates 10, or -pyrrole-2-carboxylates 13 with 1 gave 4-quinolones 7, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. Similarly, N-alkynylated alpha- or beta-amino esters 14 or 15 with 1 afforded N-heterocycles 18 or 19. In the reaction of N-(2- or 3-alkenyl)amino esters with 1, the resulting INAS product underwent intramolecular carbonyl addition (ICA) reaction to afford the N-heterocyclic compounds having a cyclopropanol moiety in good to excellent yields. Thus, the treatment of N-alkenyl-anthranilate 4a, -indole-2-carboxylates 8 and 9, or -pyrrole-2-carboxylates 11 and 12 with 1 gave the corresponding quinoline derivative 6a, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. The optically active N-heterocyclic compounds 20 and 21 were obtained from N-alkenylated alpha- or beta-amino esters 16 or 17. A highly efficient total synthesis of allopumiliotoxin alkaloid 267A has also been accomplished. Thus, the N-propargyl-2[(1-hydroxy-1-methoxycarbonyl)ethyl]pyrrolidine 24 (from L-proline in six steps) reacted with 1 to afford the corresponding indolidinone 25 in 67% yield, which has previously been converted to allopumiliotoxin 267A.