2-acetylcyclohexanone monoethyleneketal | 16111-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetylcyclohexanone monoethyleneketal
• 英文别名: 6-Acetyl-1,4-dioxaspiro<4,5>decane；1-(1,4-dioxaspiro[4.5]decan-6-yl)ethanone；2-Acetyl-cyclohexanon-aethylenketal；6-Acetyl-1,4-dioxaspiro<4,5>decan；1-(1,4-Dioxa-spiro[4.5]dec-6-yl)-aethanon；1-(1,4-dioxa-spiro[4.5]dec-6-yl)-ethanone；1-{1,4-Dioxaspiro[4.5]decan-6-yl}ethanone
• CAS: 16111-99-2
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: JSDPRMAAGLFEDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  2-acetylcyclohexanone monoethyleneketal 在 一水合肼 、 barium(II) oxide 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Synthesis of 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides from 2-acetylcyclohexanone via palladium-catalysed aminocarbonylation

  摘要：

  6-(1-Iodovinyl)-1,4-dioxaspiro[4.5]decane, an iodoalkene obtained from 2-acetylcyclohexanone via ethylene ketal formation, hydrazone formation and iodination, was aminocarbonylated in the presence of a palladium-phosphine precatalyst. Systematic investigations revealed that 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides can be obtained in high yields via palladium-catalysed aminocarbonylation. The influence of the amine nucleophiles and of the reaction conditions on the isolated yields was investigated.

  DOI：

  10.1007/s00706-015-1535-3
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 1,4-二氧六环 、 氢氧化钾 、 乙二醇 作用下， 生成 2-acetylcyclohexanone monoethyleneketal
  参考文献：
  名称：

  Kotschetkow et al., Zhurnal Obshchei Khimii, 1960, vol. 30, p. 2275,2279; engl. Ausg. S. 2257, 2261

  摘要：

  DOI：

文献信息

• Dialkylation of β and γ-diketone monoethyleneketals by 1,8-bis(trimethylsilyl)-2,6-octadiene.
  作者：Hélène Pellissier、Arlette Tubul、Maurice Santelli

  DOI：10.1016/0040-4039(93)89023-j

  日期：1993.1

  Dialkylation of β-diketone monoethyleneketals by 1,8-bis(trimethylsilyl)-2,6-octadiene leads to bi- or tricyclic alcohols (one stereoisomer) 3 or 7a resulting from a participation reaction. On the other hand, dialkylation of 2,5-hexanedione monoethyleneketal gives a divinylbicyclic ether 10

  β-二酮单亚乙基缩酮被1,8-双（三甲基甲硅烷基）-2,6-辛二烯二烷基化可导致参与反应，从而形成双环或三环醇（一种立体异构体）3或7a。另一方面，2,5-己二酮单亚乙基缩酮的二烷基化得到二乙烯基双环醚10
• Novel stereocontrolled syntheses of exocyclic γ-oxovinyltrimethylsilanes. A potential route for stereodefined exocyclic tetrasubstituted alkenes
  作者：Kazuhiko Nakatani、Tomoko Izawa、Yoshihiko Odagaki、Sachihiko Isoe

  DOI：10.1039/c39930001365

  日期：——

  The course of the dehydration of α-hydroxy-γ-oxotrimethylsilanes is highly dependent on the conditions to produce stereoselectively (Z)- and (E)-γ-oxovinyltrirnethylsilanes, which are potential precursors for preparation of stereodefined exocyclic tetrasubstituted alkenes.

  δ-羟基-δ-氧代三甲基硅烷的脱水过程在很大程度上取决于生成立体选择性 (Z)- 和 (E)- δ-氧代乙烯基三irnethyl 硅烷的条件，这些硅烷是制备立体定义的外环四取代烯的潜在前体。
• 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.
• Kochetkov,N.K. et al., Journal of general chemistry of the USSR, 1960, vol. 30, p. 2257 - 2263
  作者：Kochetkov,N.K. et al.

  DOI：——

  日期：——
• Kotschetkow et al., Khimicheskaya Nauka i Promyshlennost, 1959, vol. 4, p. 808
  作者：Kotschetkow et al.

  DOI：——

  日期：——