(4R)-4-isopropyl-5-vinyloxazolidin-2-one | 880360-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-4-isopropyl-5-vinyloxazolidin-2-one
• 英文别名: (4S)-4-isopropyl-5-vinyloxazolidin-2-one；(4S)-5-ethenyl-4-(2-propyl)oxazolidin-2-one；(4S,5RS)-5-ethenyl-4-(2-propyl)oxazolidin-2-one；(4S)-5-Ethenyl-4-(1-methylethyl)-2-oxazolidinone；(4S)-5-ethenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 880360-25-8
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: ZIOMABMTSSKCDC-MLWJPKLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (4R)-4-isopropyl-5-vinyloxazolidin-2-one 在 tris(dibenzylideneacetone)dipalladium (0) 一氧化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (6S)-3,6-dihydro-6-isopropyl-1-[(4-methylbenzene)sulfonyl]pyridin-2-one
  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
• 作为产物：
  描述：

  N-BOC-2(S)-2-AMINO-3-METHYL-BUTAL聽 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (4R)-4-isopropyl-5-vinyloxazolidin-2-one
  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

• Improved Stereoselectivity in Intramolecular S_N2′ Cyclization through Use of Mechanistic Principles
  作者：Ki Park、Woo Seo、Marcus Curtis-Long、Seong Jeong、Tae Jun、Min Yang

  DOI：10.1055/s-2006-958956

  日期：2007.1

  Valine and alanine were converted into the corresponding α-hydroxy-β-amino acids through intramolecular S N 2' cyclization. The novel cyclization protocol relied upon the use of N-benzyl-protected carbamates derived from α-amino acids.

  缬氨酸和丙氨酸通过分子内SN 2' 环化转化为相应的α-羟基-β-氨基酸。新的环化方案依赖于使用衍生自 α-氨基酸的 N-苄基保护的氨基甲酸酯。
• 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
• Diastereospecific carbonylation of π-allylpalladium complexes to give 3,6-disubstituted 3,6-dihydro-1H-pyridin-2-ones
  作者：Julian G Knight、Kirill Tchabanenko

  DOI：10.1016/s0040-4020(02)00683-x

  日期：2002.8

  (Ph3P)(2)PdCl2 was found to be the most effective of a range of catalysts for decarboxylative carbonylation of (4S,5RS)-5-ethenyl-4-(2-propyl)oxazolidin-2-one to give the delta-lactam, (6S)-3,6-dihydro-6-(2-propyl)-1H-pyridin-2-one. In a similar way, diastereoisomerically pure (4S,5S)-4-benzyl-5-((Z)alk-1-enyl)oxazolidin-2-ones undergo stereospecific carbonylation to give (3R,6S)-6-benzyl-3-alkyl-3,6-dihydro-1H-pyridin-2-ones. The diastereoisomeric (4S,5R)-4-benzyl-5-((Z)alk-1-enyl)oxazolidin-2-ones give rise to a separable mixture of the corresponding (3S,6S)-6-benzyl-3-alkyl-3,6-dihydro-1H-pyridin-2-one and (4S,5S)-4-benzyl-5-((E)alk-1-enyl)oxazolidin-2-one. Under more forcing conditions, the latter oxazolidinone is carbonylated to the 3,6-anti-pyridinone. The stereochemical course of the reactions can be rationalized by formation of a pi-allyl palladium cation with inversion of configuration followed by carbonylation with retention. The stereospecificity observed in our system precludes metal-metal exchange of the pi-allyl complexes by a Pd(0) displacement process. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.
• 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。