(+)-tert-butyl (1R,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate | 1233220-23-9

• 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)-4-(hydroxymethyl)cyclopent-2-enylcarbamate
• 英文别名: tert-butyl N-[(1R,4R)-4-(hydroxymethyl)cyclopent-2-en-1-yl]carbamate
• CAS: 1233220-23-9
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: MVIWPMBRXBNBDX-IUCAKERBSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  338.8±31.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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

• 作为反应物：
  描述：

  (+)-tert-butyl (1R,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以100%的产率得到((1R,4R)-4-Aminocyclopent-2-en-1-yl)methanol hydrochloride
  参考文献：
  名称：

  碳环氨基核苷和 (-)-epi-4'-碳环嘌呤霉素的合成：钯 (0)/碘化铟烯丙基化和束缚氨基羟基化的应用

  摘要：

  碳环氨基核苷和epi -4'-碳环嘌呤霉素由酰基亚硝基衍生的杂Diels-Alder环加合物制备。Pd(0)/InI 介导的甲酰基烯丙基化被用于安装 4'-羟甲基。采用束缚氨基羟基化策略来安装具有完全区域和非对映控制的顺式-2',3'-氨基醇部分。

  DOI：

  10.1016/j.tetlet.2010.04.006
• 作为产物：
  描述：

  Acetic acid 1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thiopyran-3-ylmethyl ester 在 ammonium hydroxide 、 potassium tert-butylate 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+)-tert-butyl (1R,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate
  参考文献：
  名称：

  The synthesis of trans -carbovir via the ramberg-bäcklund reaction

  摘要：

  A novel Ramberg-Backlund approach to the synthesis of 1-amino-4-substituted cyclopentenes is described and applied to prepare the trans-isomer of the carbocyclic nucleoside carbovir.

  DOI：

  10.1016/0040-4039(95)01621-n

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.
• Syntheses of carbocyclic aminonucleosides and (−)-epi-4′-carbocyclic puromycin: application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations
  作者：Cara Cesario、Lawrence P. Tardibono、Marvin J. Miller

  DOI：10.1016/j.tetlet.2010.04.006

  日期：2010.6

  puromycin were prepared from an acylnitroso-derived hetero Diels–Alder cycloadduct. Pd(0)/InI-mediated allylations of a formyl species were used to install the 4′-hydroxymethyl group. A tethered aminohydroxylation strategy was employed to install the cis-2′,3′-aminoalcohol moiety with complete regio- and diastereocontrol.

  碳环氨基核苷和epi -4'-碳环嘌呤霉素由酰基亚硝基衍生的杂Diels-Alder环加合物制备。Pd(0)/InI 介导的甲酰基烯丙基化被用于安装 4'-羟甲基。采用束缚氨基羟基化策略来安装具有完全区域和非对映控制的顺式-2',3'-氨基醇部分。
• The synthesis of trans -carbovir via the ramberg-bäcklund reaction
  作者：Arne Grumann、Hugh Marley、Richard J.K. Taylor

  DOI：10.1016/0040-4039(95)01621-n

  日期：1995.10

  A novel Ramberg-Backlund approach to the synthesis of 1-amino-4-substituted cyclopentenes is described and applied to prepare the trans-isomer of the carbocyclic nucleoside carbovir.