tert-butyl (S,E)-1-isopropyl-4-trimethylsilanyl-but-2-enyl-carbamate | 1140504-25-1

• 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: tert-butyl (S,E)-1-isopropyl-4-trimethylsilanyl-but-2-enyl-carbamate
• 英文别名: tert-butyl N-[(E,3S)-2-methyl-6-trimethylsilylhex-4-en-3-yl]carbamate
• CAS: 1140504-25-1
• 化学式: C₁₅H₃₁NO₂Si
• 分子量: 285.502
• InChiKey: BPWOCMZFSMFHLD-WTNCMQEWSA-N

物化性质

• 沸点：
  352.9±35.0 °C(predicted)
• 密度：
  0.896±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (S,E)-1-isopropyl-4-trimethylsilanyl-but-2-enyl-carbamate 在 碳酸氢钠 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以98%的产率得到(3S,4RS)-2-methyl-3-tert-butoxycarbonylamino-4-fluoro-5-hexene
  参考文献：
  名称：

  New enantiomerically enriched amino allyl- and allenylsilanes derived from naturally occurring amino acids

  摘要：

  Some enantiomerically enriched Z-amino allylsilanes and allenylsilanes have been obtained selectively through the synthetic elaboration of naturally occurring amino acids. Fluorodesilylation with Selectfluor (R) has been proved as an easy way for preparing allylic fluorides bearing an amino or an amino acid moiety on the lateral chain. In particular, a new unsaturated fluorinated amino acid has been obtained, albeit as a diastereomeric mixture. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.025
• 作为产物：
  描述：

  N-BOC-2(S)-2-AMINO-3-METHYL-BUTAL聽 在 4-二甲氨基吡啶 、 甲基锂 、 copper(l) cyanide 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 为溶剂， 生成 tert-butyl (S,E)-1-isopropyl-4-trimethylsilanyl-but-2-enyl-carbamate
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes

  摘要：

  An efficient synthesis of various protected syn-beta-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral beta-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.

  DOI：

  10.1021/jo2010878

文献信息

• Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes
  作者：Gianna Reginato、Bernardo Pezzati、Andrea Ienco、Gabriele Manca、Andrea Rossin、Alessandro Mordini

  DOI：10.1021/jo2010878

  日期：2011.9.16

  An efficient synthesis of various protected syn-beta-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral beta-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.
• New enantiomerically enriched amino allyl- and allenylsilanes derived from naturally occurring amino acids
  作者：Gianna Reginato、Alessandro Mordini、Alice Tenti、Michela Valacchi、Julie Broguiere

  DOI：10.1016/j.tetasy.2008.12.025

  日期：2008.12

  Some enantiomerically enriched Z-amino allylsilanes and allenylsilanes have been obtained selectively through the synthetic elaboration of naturally occurring amino acids. Fluorodesilylation with Selectfluor (R) has been proved as an easy way for preparing allylic fluorides bearing an amino or an amino acid moiety on the lateral chain. In particular, a new unsaturated fluorinated amino acid has been obtained, albeit as a diastereomeric mixture. (C) 2009 Elsevier Ltd. All rights reserved.