(3RS,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-methylhex-1-en-3-ol | 477781-32-1

• 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: (3RS,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-methylhex-1-en-3-ol
• 英文别名: (3RS,4S)-4-N-(tert-butoxycarbonyl)amino-3-hydroxy-5-methylhex-1-ene；tert-butyl N-[(3S)-4-hydroxy-2-methylhex-5-en-3-yl]carbamate
• CAS: 477781-32-1
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: PUJZPMGNMZHBAB-AXDSSHIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3RS,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-methylhex-1-en-3-ol 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 、 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
• 作为产物：
  描述：

  N-Boc-L-缬氨醇 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (3RS,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-methylhex-1-en-3-ol
  参考文献：
  名称：

  3,6-Dihydro-1H-pyridin-2-ones 的对映体特异性形成：3-Tosyl-5-vinyloxazolidin-2-ones 的低压钯催化脱羧羰基化

  摘要：

  钯催化的 3-tosyl-5-vinyloxazolidin-2-ones 5 的脱羧羰基化反应在大气压下发生，得到 1-tosyl-3,6-dihydro-1H-pyridin-2-ones 6。反应进行时没有损失对映体纯度和用萘钠去甲苯基化以良好的收率得到标题化合物。

  DOI：

  10.1055/s-2005-924765

文献信息

• Enantioselective Synthesis of 3,6-Dihydro-1<i>H</i>-pyridin-2-ones:  Unexpected Regioselectivity in the Palladium-Catalyzed Decarboxylative Carbonylation of 5-Vinyloxazolidin-2-ones
  作者：Julian G. Knight、Simon W. Ainge、Andrew M. Harm、Simon J. Harwood、Haydn I. Maughan、Duncan R. Armour、David M. Hollinshead、Albert A. Jaxa-Chamiec

  DOI：10.1021/ja993897c

  日期：2000.3.1
• Asymmetric synthesis of β2,3-amino acids by InI–Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines
  作者：Miyuki Anzai、Reiko Yanada、Nobutaka Fujii、Hiroaki Ohno、Toshiro Ibuka、Yoshiji Takemoto

  DOI：10.1016/s0040-4020(02)00499-4

  日期：2002.6

  The reaction of optically active 3-alkyl-2-vinylaziridines with various aldehydes in the presence of InI and Pd(PPh3)(4) gives rise to chiral syn,syn-2-vinyl-1,3-amino alcohols possessing three contiguous chiral centers stereoselectively. The ratio of the syn,syn-isomer to the other three isomers is significantly affected by the C3-substituents of aziridines as well as the alkyl groups of aldehydes. In addition, the obtained 1,3-aminoalcohols can be converted into biologically important p(2,3)-amino acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.
• Enantiospecific Formation of 3,6-Dihydro-1<i>H</i>-pyridin-2-ones: Low-Pressure Palladium-Catalysed Decarboxylative Carbonylation of 3-Tosyl-5-vinyloxazolidin-2-ones
  作者：Julian G. Knight、Iain M. Lawson、Christopher N. Johnson

  DOI：10.1055/s-2005-924765

  日期：——

  Palladium-catalysed decarboxylative carbonylation of 3-tosyl-5-vinyloxazolidin-2-ones 5 occurs at atmospheric pressure to give 1-tosyl-3,6-dihydro-1H-pyridin-2-ones 6. The reaction proceeds with no loss of enantiopurity and detosylation with sodium naphthalenide gives the title compounds in good yields.

  钯催化的 3-tosyl-5-vinyloxazolidin-2-ones 5 的脱羧羰基化反应在大气压下发生，得到 1-tosyl-3,6-dihydro-1H-pyridin-2-ones 6。反应进行时没有损失对映体纯度和用萘钠去甲苯基化以良好的收率得到标题化合物。