(+)-tert-butyl (1R,4R)-2-(hydroxymethyl)cyclopent-3-enylcarbamate | 1233220-24-0

• 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 (1R,4R)-2-(hydroxymethyl)cyclopent-3-enylcarbamate
• 英文别名: tert-butyl N-[(1R,2R)-2-(hydroxymethyl)cyclopent-3-en-1-yl]carbamate
• CAS: 1233220-24-0
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: PVJHDXXDDXKRGL-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  n,n-二甲基亚甲基碘化胺 、 (1S,4R)-乙酸-4-叔丁氧羰基氨基-环戊基-2-烯酯 在 indium iodide 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.67h， 以49%的产率得到(+)-tert-butyl (1R,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate
  参考文献：
  名称：

  Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser’s salt: one-pot preparation of diverse carbocyclic scaffolds

  摘要：

  A formyl equivalent was generated in situ from Eschenmoser's salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels-Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.007

文献信息

• Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser’s salt: one-pot preparation of diverse carbocyclic scaffolds
  作者：Cara Cesario、Marvin J. Miller

  DOI：10.1016/j.tetlet.2010.04.007

  日期：2010.6

  A formyl equivalent was generated in situ from Eschenmoser's salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels-Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate. (C) 2010 Elsevier Ltd. All rights reserved.