2-[(trimethylsilyl)methyl]-2-propen-1-yl N,N-bis(isopropyl)carbamate | 307344-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(trimethylsilyl)methyl]-2-propen-1-yl N,N-bis(isopropyl)carbamate
• 英文别名: 2-[(trimethylsilyl)methyl]-2-propen-1-yl-bis(isopropyl) carbamate；2-[(trimethylsilyl)methyl]-2-propen-1-yl bis(isopropyl)carbamate；2-((trimethylsilyl)methyl)allyl diisopropylcarbamate；2-trimethylsilylmethylallyl-diisopropylcarbamate；2-(trimethylsilylmethyl)prop-2-enyl N,N-di(propan-2-yl)carbamate
• CAS: 307344-40-7
• 化学式: C₁₄H₂₉NO₂Si
• 分子量: 271.475
• InChiKey: NXBNGPALFCELMC-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±31.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  2-[(trimethylsilyl)methyl]-2-propen-1-yl N,N-bis(isopropyl)carbamate 在 二甲基硫 、 四甲基乙二胺 、 三氟化硼乙醚 、 仲丁基锂 、 L-Selectride 、 臭氧 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 syn-4-hydroxy-2,6-dipropyl-tetrahydropyran-3-yl-diisopropylcarbamate
  参考文献：
  名称：

  简明和立体控制的多取代四氢吡喃的合成

  摘要：

  一系列多取代的四氢吡喃可以很容易地通过一种新颖的方法进行组装，该方法涉及金属茂反应与分子内樱井环化反应（IMSC）

  DOI：

  10.1016/s0040-4039(00)01179-5
• 作为产物：
  描述：

  二异丙基甲胺酰氯 、 2-[(三甲基硅烷基)甲基]-2-丙烯-1-醇 在 sodium hydride 作用下， 以 乙醚 、 mineral oil 为溶剂， 以82%的产率得到2-[(trimethylsilyl)methyl]-2-propen-1-yl N,N-bis(isopropyl)carbamate
  参考文献：
  名称：

  吡喃糖基C-核苷合成的区域和立体控制方法。

  摘要：

  使用烯/分子内Sakurai环化反应从非手性原料合成了六种新的非对映异构纯C核苷，表明对吡喃糖基C核苷有简单，通用且立体控制的方法。

  DOI：

  10.1021/ol801183e

文献信息

• Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid
  作者：Christophe Dubost、Bernard Leroy、Istvan E. Markó、Bernard Tinant、Jean-Paul Declercq、Justin Bryans

  DOI：10.1016/j.tet.2004.06.084

  日期：2004.8

  Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.
• Connective Synthesis of Polysubstituted Tetrahydropyrans by a Novel and Stereocontrolled Metallo-ene/Intramolecular Sakurai Cyclization Sequence
  作者：Bernard Leroy、István E. Markó

  DOI：10.1021/jo025899c

  日期：2002.12.1

  A novel methodology based upon the allylmetalation step followed by an Intramolecular Sakurai Cyclization (IMSC) provides an efficient access to a variety of tetrahydropyran derivatives. This new strategy nicely complements our initial protocol that embodied a tandem ene reaction/IMSC sequence. Both mono- and dihydroxy-tetrahydropyrans could be easily assembled with complete stereocontrol at the various chiral centers.
• Rapid and Versatile Synthesis of Functionalized Polyhydroxylated Fragments
  作者：Bernard Leroy、István E. Markó

  DOI：10.1021/ol016863u

  日期：2002.1.1

  [GRAPHICS]The condensation between a functionalized allylstannane and alpha-alkoxyaldehydes allows rapid access to complex and selectively protected trihydroxylated synthons. The stereocontrol of this process is strongly dependent upon the nature and the amount of the Lewis acid employed.
• Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties
  作者：Philip Redpath、Kerry A. Ness、Joanne Rousseau、Simon J.F. Macdonald、Marie E. Migaud

  DOI：10.1016/j.carres.2014.10.030

  日期：2015.1

  The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (+/-)-beta-2-deoxy-glucose6-phosphate.[GRAPHICS](C) 2014 Elsevier Ltd. All rights reserved.