2-(5-Hexenyl)-2-methyl-1,3-dioxolane | 15144-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-Hexenyl)-2-methyl-1,3-dioxolane
• 英文别名: 2--2-methyl-<1,3>-dioxolan；2-hex-5-enyl-2-methyl-[1,3]dioxolane；2-Hex-5-enyl-2-methyl-1,3-dioxolane
• CAS: 15144-28-2
• 化学式: C₁₀H₁₈O₂
• mdl: MFCD11553758
• 分子量: 170.252
• InChiKey: BJNUNKNYTDAANA-UHFFFAOYSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  206.7±15.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-Hexenyl)-2-methyl-1,3-dioxolane 在 硫酸 作用下， 生成 辛-7-烯-2-酮
  参考文献：
  名称：

  Feugeas,C., Bulletin de la Societe Chimique de France, 1963, p. 2568 - 2579

  摘要：

  DOI：
• 作为产物：
  描述：

  辛-7-烯-2-酮 、 乙二醇 生成 2-(5-Hexenyl)-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Stereochemical Investigations of Samarium(II) Iodide-Promoted 5-Exo and 6-Exo Ketyl-Olefin Radical Cyclization Reactions

  摘要：

  Samarium(II) iodide (SmI2)-promoted ketyl cyclizations of several substituted, unsaturated ketones, providing various cyclopentyl and cyclohexyl systems, have been investigated. The resulting experiments provide stereochemical insight into these reactions and in addition outline the synthetic potential of these 5-exe and 6-exo radical cyclization processes.

  DOI：

  10.1021/jo00109a018

文献信息

• Scope and mechanism of the electron transfer photoinduced alkylation of an aromatic nitrile
  作者：Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1016/s0040-4020(01)80656-6

  日期：1994.1

  The photoinduced alkylation of 1,2,4,5-tetracyanobenzene in the presence of tetralkylsilane or - stannane derivatives as well of 2,2-dialkyldioxolanes

  在四烷基硅烷或-锡烷衍生物以及2,2-二烷基二氧戊环存在下，对1,2,4,5-四氰基苯进行光诱导的烷基化
• Synthesis of Substituted Cyclooctanols by a Samarium(II) Iodide Promoted 8-Endo Radical Cyclization Process
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00090a041

  日期：1994.6

  Samarium(II) iodide (SmI2) has been employed to promote an efficient 8-endo radical cyclization reaction of a variety of substituted olefinic ketones. Various substituted monocyclic, fused bicyclic, and bridged bicyclic cyclooctanols have been synthesized in fair to excellent yield via this protocol. In addition to delineating the synthetic potential of this reaction, experiments have been conducted to determine the source of reduced, noncyclized byproducts present in this and related SmI2-mediated reactions performed under protic conditions.
• Electron transfer photoinduced cleavage of acetals. A mild preparation of alkyl radicals
  作者：M. Mella、E. Fasani、A. Albini

  DOI：10.1021/jo00037a020

  日期：1992.5

  Electron transfer from 2-alkyl- and 2,2-dialkyldioxolanes as well as from open-chain ketals to singlet excited benzene-1,2,4,5-tetracarbonitrile (TCNB) is followed by fragmentation of the donors radical cation to yield alkyl radicals and dialkoxy carbocations. The first species are trapped by TCNB to yield alkylbenzenetricarbonitriles (substitution of a second cyano group can be obtained sequentially) and in a minor path are reduced to alkanes, while the latter ones react with nucleophiles to give ortho acid derivatives. In view of the results of radical clock experiments, it is assumed that part of the process is a concerted (radical cation cleavage-addition to the aromatic) reaction, while another part involves the free-radical cation. On the other hand, intersystem crossing from the singlet radical ion pair to the triplet manifold causes cleavage of the acetal to the corresponding carbonyl derivative. This reaction offers a mild method for the preparation of alkyl radicals via C-C bond cleavage.
• Feugeas,C., Bulletin de la Societe Chimique de France, 1963, p. 2568 - 2579
  作者：Feugeas,C.

  DOI：——

  日期：——
• Stereochemical Investigations of Samarium(II) Iodide-Promoted 5-Exo and 6-Exo Ketyl-Olefin Radical Cyclization Reactions
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00109a018

  日期：1995.2

  Samarium(II) iodide (SmI2)-promoted ketyl cyclizations of several substituted, unsaturated ketones, providing various cyclopentyl and cyclohexyl systems, have been investigated. The resulting experiments provide stereochemical insight into these reactions and in addition outline the synthetic potential of these 5-exe and 6-exo radical cyclization processes.