4-(cyclopent-1-en-1-yl)butanal | 143267-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(cyclopent-1-en-1-yl)butanal
• 英文别名: cyclopent-1-ene-1-butanal；4-(Cyclopenten-1-yl)butanal；4-(cyclopenten-1-yl)butanal
• CAS: 143267-39-4
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: QQNQDORGYGHESC-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C(Press: 20 Torr)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(cyclopent-1-en-1-yl)butanal 在 吡啶 、 sodium hypochlorite 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 87.0h， 生成 [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] prop-2-enoate
  参考文献：
  名称：

  Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions

  摘要：

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00051-x
• 作为产物：
  描述：

  6-氧杂螺[4.5]癸烷-7-酮 在 potassium methanolate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 9.5h， 生成 4-(cyclopent-1-en-1-yl)butanal
  参考文献：
  名称：

  由α-甲酰基-γ-内酯新型合成γ，δ-不饱和醛

  摘要：

  的制备性有用的一步变换γ，γ二取代α甲酰基γ内酯到三取代的γ，δ不饱和醛进行了说明，通过在汽相中在玻璃支撑催化量的AcOH任一或乙酸乙酯的装置。提出了机械原理。

  DOI：

  10.1002/hlca.201000447

文献信息

• Spiro- and bridged-ring forming electrophile induced → oxime → nitrone cycloaddition cascades. Multiplication of chirality
  作者：H.Ali Dondas、Ronald Grigg、Christopher S. Frampton

  DOI：10.1016/s0040-4039(97)01255-0

  日期：1997.8

  Electrophile induced 6-exo-trig spirocyclisation of oximes onto 5-, 6- or 7-membered cycloalkenes occurs stereo- and regio- specifically in good yield. Bridged - ring forming cyclisations creating bicycle-[3.3.1]- and bicyclo-[3.2.1]-ring systems also occur in good yield. Chiral bridged-ring systems have been synthesised, via the latter processes, that involve multiplication of chiral centres from one to six and seven in one pot reactions. (C) 1997 Elsevier Science Ltd.
• Bunnelle, William H.; Lee, Sang-Gi, Journal of the American Chemical Society, 1992, vol. 114, # 19, p. 7577 - 7578
  作者：Bunnelle, William H.、Lee, Sang-Gi

  DOI：——

  日期：——
• A Novel Synthesis of γ,δ-Unsaturated Aldehydes from α-Formyl-γ-lactones
  作者：Roger L. Snowden、Robert Brauchli、Simon Linder

  DOI：10.1002/hlca.201000447

  日期：2011.7

  A preparatively useful one‐step transformation of γ,γ‐disubstituted α‐formyl‐γ‐lactones into trisubstituted γ,δ‐unsaturated aldehydes is described, by means of catalytic amounts of either AcOH or AcOEt in the vapor phase over a glass support. A mechanistic rationale is proposed.

  的制备性有用的一步变换γ，γ二取代α甲酰基γ内酯到三取代的γ，δ不饱和醛进行了说明，通过在汽相中在玻璃支撑催化量的AcOH任一或乙酸乙酯的装置。提出了机械原理。
• Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions
  作者：Susan M. Lait、Masood Parvez、Brian A. Keay

  DOI：10.1016/s0957-4166(03)00051-x

  日期：2003.3

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.