α-propargyloxymethyl-cyclopentanone | 870194-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-propargyloxymethyl-cyclopentanone
• 英文别名: 2-(Prop-2-ynoxymethyl)cyclopentan-1-one；2-(prop-2-ynoxymethyl)cyclopentan-1-one
• CAS: 870194-19-7
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: MXQWOXPMDVNHHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-propargyloxymethyl-cyclopentanone 以 乙腈 为溶剂， 反应 24.0h， 以14%的产率得到(3R,3aR,6aS)-3-Ethynyl-tetrahydro-cyclopenta[c]furan-3a-ol
  参考文献：
  名称：

  Synthesis and photoinitiated radical cyclization of allyl- and propynyloxymethyl substituted cyclopentanones to tetrahydrocyclopenta[c]furanols

  摘要：

  Bicyclic cyclopentafuranols were formed by photoinitiated radical cyclization of allyl- and propinyloxymethyl substituted cyclopentanones with high regioselectivity. The irradiations were carried out at a wavelength of 300 nm in aprotic solvents such as benzene and acetonitrile. We could also show that reductive photoinduced electron transfer (PET) of the propynyloxymethyl substituted cyclopentanone 5 does not lead to any cyclization. The starting materials were synthesized in good yields following known procedures. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.040
• 作为产物：
  描述：

  2-亚乙二氧基环戊环羧酸乙酯 在 lithium aluminium tetrahydride 、 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 α-propargyloxymethyl-cyclopentanone
  参考文献：
  名称：

  Synthesis and photoinitiated radical cyclization of allyl- and propynyloxymethyl substituted cyclopentanones to tetrahydrocyclopenta[c]furanols

  摘要：

  Bicyclic cyclopentafuranols were formed by photoinitiated radical cyclization of allyl- and propinyloxymethyl substituted cyclopentanones with high regioselectivity. The irradiations were carried out at a wavelength of 300 nm in aprotic solvents such as benzene and acetonitrile. We could also show that reductive photoinduced electron transfer (PET) of the propynyloxymethyl substituted cyclopentanone 5 does not lead to any cyclization. The starting materials were synthesized in good yields following known procedures. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.040

文献信息

• Synthesis and photoinitiated radical cyclization of allyl- and propynyloxymethyl substituted cyclopentanones to tetrahydrocyclopenta[c]furanols
  作者：Nikolay T. Tzvetkov、Jochen Mattay

  DOI：10.1016/j.tetlet.2005.09.040

  日期：2005.11

  Bicyclic cyclopentafuranols were formed by photoinitiated radical cyclization of allyl- and propinyloxymethyl substituted cyclopentanones with high regioselectivity. The irradiations were carried out at a wavelength of 300 nm in aprotic solvents such as benzene and acetonitrile. We could also show that reductive photoinduced electron transfer (PET) of the propynyloxymethyl substituted cyclopentanone 5 does not lead to any cyclization. The starting materials were synthesized in good yields following known procedures. (c) 2005 Elsevier Ltd. All rights reserved.