6-Acetyl-1,4-dioxaspiro<4.4>nonane | 16111-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Acetyl-1,4-dioxaspiro<4.4>nonane
• 英文别名: 1-(1,4-dioxa-spiro[4.4]non-6-yl)-ethanone；1-(1,4-Dioxa-spiro[4.4]non-6-yl)-aethanon；1-(1,4-Dioxaspiro[4.4]nonan-9-yl)ethanone
• CAS: 16111-98-1
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: DLYNVAVICIRXAM-UHFFFAOYSA-N

物化性质

• 沸点：
  115-116 °C(Press: 16 Torr)
• 密度：
  1.1170 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Acetyl-1,4-dioxaspiro<4.4>nonane 在 甲基锂 、 4-甲基苯磺酸吡啶 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.25h， 生成 (E)-2-<1-(Trimethylsilyl)ethylidene>cyclopentanone
  参考文献：
  名称：

  Syntheses and Theoretical Studies of Exocyclic .gamma.-Oxoalkenyltrimethylsilanes. An Approach to the Stereodefined Exocyclic Tetrasubstituted Alkenes

  摘要：

  The Z-selectivity in the dehydration of alpha-hydroxy-gamma-oxoalkyltrimethylsilanes under acidic conditions was studied from experimental and theoretical points of view. Experimental results showed that (Z)-gamma-oxoalkenyltrimethylsilanes were thermodynamic products under these conditions. The dehydration studies of the compound involving the tert-butyl group instead of the TMS group pointed out that not only steric but also electronic effects of Si could contribute to the distribution of the products as well as their stereochemistries. Theoretical studies using ab initio calculation at the 6-31G* level indicated that the (Z)-isomer was thermodynamically more stable than the corresponding (E)-isomer. Detail examinations of the optimized structures showed that the configuration of Si in the (Z)-isomer was slightly distorted from tetrahedral. Interpretation of the geometrical change of Si to rationalization of the thermodynamic preference was discussed fi om the viewpoint of possible coordination of the carbonyl oxygen to Si. Those (Z)-gamma-oxoalkenyltrimethylsilanes would have potential to be the novel type of alkenylmetal compounds in organic synthesis as we demonstrated in the construction of stereodefined exocyclic tetrasubstituted alkene.

  DOI：

  10.1021/jo00099a027
• 作为产物：
  描述：

  1-acetoxycyclopentene 在 氢氧化钾 、 三氯化铝 、 乙二醇 、 1,2-二氯乙烷 作用下， 生成 6-Acetyl-1,4-dioxaspiro<4.4>nonane
  参考文献：
  名称：

  Kotschetkow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2330,2336; engl. Ausg. S. 2294, 2299

  摘要：

  DOI：

文献信息

• Syntheses and Theoretical Studies of Exocyclic .gamma.-Oxoalkenyltrimethylsilanes. An Approach to the Stereodefined Exocyclic Tetrasubstituted Alkenes
  作者：Kazuhiko Nakatani、Tomoko Izawa、Sachihiko Isoe

  DOI：10.1021/jo00099a027

  日期：1994.10

  The Z-selectivity in the dehydration of alpha-hydroxy-gamma-oxoalkyltrimethylsilanes under acidic conditions was studied from experimental and theoretical points of view. Experimental results showed that (Z)-gamma-oxoalkenyltrimethylsilanes were thermodynamic products under these conditions. The dehydration studies of the compound involving the tert-butyl group instead of the TMS group pointed out that not only steric but also electronic effects of Si could contribute to the distribution of the products as well as their stereochemistries. Theoretical studies using ab initio calculation at the 6-31G* level indicated that the (Z)-isomer was thermodynamically more stable than the corresponding (E)-isomer. Detail examinations of the optimized structures showed that the configuration of Si in the (Z)-isomer was slightly distorted from tetrahedral. Interpretation of the geometrical change of Si to rationalization of the thermodynamic preference was discussed fi om the viewpoint of possible coordination of the carbonyl oxygen to Si. Those (Z)-gamma-oxoalkenyltrimethylsilanes would have potential to be the novel type of alkenylmetal compounds in organic synthesis as we demonstrated in the construction of stereodefined exocyclic tetrasubstituted alkene.
• Kotschetkow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2330,2336; engl. Ausg. S. 2294, 2299
  作者：Kotschetkow et al.

  DOI：——

  日期：——