6-Prop-2-ynyloxymethyl-1,4-dioxa-spiro[4.4]nonane | 870194-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Prop-2-ynyloxymethyl-1,4-dioxa-spiro[4.4]nonane
• 英文别名: 9-(Prop-2-ynoxymethyl)-1,4-dioxaspiro[4.4]nonane；9-(prop-2-ynoxymethyl)-1,4-dioxaspiro[4.4]nonane
• CAS: 870194-18-6
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: GVHPZWYXIABJKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Prop-2-ynyloxymethyl-1,4-dioxa-spiro[4.4]nonane 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以32%的产率得到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
• 作为产物：
  描述：

  2-亚乙二氧基环戊环羧酸乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 6-Prop-2-ynyloxymethyl-1,4-dioxa-spiro[4.4]nonane
  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.