2-(1-Ethylpropyl)-1,3-dioxolane | 17155-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(1-Ethylpropyl)-1,3-dioxolane
• 英文别名: 2-(pentan-3-yl)-1,3-dioxolane；2-Pentan-3-yl-1,3-dioxolane
• CAS: 17155-64-5
• 化学式: C₈H₁₆O₂
• mdl: MFCD06209009
• 分子量: 144.214
• InChiKey: DTOBWZCLJPLSTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,2,4,5-四氰基苯 、 2-(1-Ethylpropyl)-1,3-dioxolane 以 乙腈 为溶剂， 反应 2.5h， 以61%的产率得到5-(1-Ethylpropyl)-1,2,4-tricyanobenzene
  参考文献：
  名称：

  Electron transfer photoinduced cleavage of acetals. A mild preparation of alkyl radicals

  摘要：

  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.

  DOI：

  10.1021/jo00037a020
• 作为产物：
  描述：

  2-ethylbutyraldehyde oxime 在 1,1,1,3,3,3-六溴丙酮 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 2-(1-Ethylpropyl)-1,3-dioxolane
  参考文献：
  名称：

  利用六溴丙酮保护醇和醛，并在紫外线照射下使乙缩醛，缩酮和肟脱保护

  摘要：

  六溴丙酮（HBA）有效地用于保护醇和醛，以及对苯甲醛二甲基乙缩醛，Solketal以及其他缩醛和缩酮进行脱保护。在仅10分钟内，甘油的保护产生了90％的solketal，苯甲醛的保护得到了95％的苯甲醛二甲基乙缩醛。仅用2.5mol％的HBA，在15秒内在UV辐射下苯甲醛二甲基乙缩醛的脱保护得到超过90％的苯甲醛产率。HBA还成功用于脱氧。发现溶剂在这些反应的HBA效率中起着重要作用。

  DOI：

  10.1007/s11164-017-3168-0

文献信息

• Visible-Light-Induced Acetalization of Aldehydes with Alcohols
  作者：Hong Yi、Linbin Niu、Shengchun Wang、Tianyi Liu、Atul K. Singh、Aiwen Lei

  DOI：10.1021/acs.orglett.6b03403

  日期：2017.1.6

  have achieved a simple and general method for acetalization of aldehydes by means of a photochemical reaction under low-energy visible light irradiation. A broad range of aromatic, heteroaromatic, and aliphatic aldehydes have been protected under neutral conditions in good to excellent yields using a catalytic amount of Eosin Y as the photocatalyst. Our visible light mediated acetalization strategies are

  在这项工作中，我们通过在低能可见光照射下进行光化学反应，实现了一种简单而通用的醛缩醛化方法。使用催化量的曙红Y作为光催化剂，在中性条件下以良好或优异的收率保护了多种芳香族，杂芳香族和脂肪族醛。我们的可见光介导的缩醛化策略可成功用于更具挑战性的酸敏感性醛和位阻醛。值得注意的是，该方案对醛具有化学选择性，而酮则保持完整。
• Alkyl Acetal Compound, Process for Producing the Same, and Lubricating Oil Composition
  申请人：Sato Haruhito

  公开号：US20080234152A1

  公开（公告）日：2008-09-25

  A compound which satisfies requirements for the annealing property and the lubricating property simultaneously and a process for producing the compound are provided. The compound is an alkylacetal compound represented by the following general formula (1) or (2). In the general formulae, R 1 and R 2 represent hydrocarbon groups, R 3 to R 8 represent hydrogen atom or hydrocarbon groups, i and j represent integers satisfying the relation that the sum of the integers is 8 to 98, and k represents 0 or 1.
• US7838692B2
  申请人：——

  公开号：US7838692B2

  公开（公告）日：2010-11-23
• Utilization of hexabromoacetone for protection of alcohols and aldehydes and deprotection of acetals, ketals, and oximes under UV irradiation
  作者：Kittichai Chaiseeda、Ladawan Chantharadet、Warinthorn Chavasiri

  DOI：10.1007/s11164-017-3168-0

  日期：2018.2

  Hexabromoacetone (HBA) was efficiently used for the protection of alcohols and aldehydes and deprotection of benzaldehyde dimethyl acetal, solketal, and other acetals and ketals. In only 10 min, the protection of glycerol yielded 90% of solketal and protection of benzaldehyde gave 95% of benzaldehyde dimethyl acetal. The deprotection of benzaldehyde dimethyl acetal under UV irradiation gave over 90%

  六溴丙酮（HBA）有效地用于保护醇和醛，以及对苯甲醛二甲基乙缩醛，Solketal以及其他缩醛和缩酮进行脱保护。在仅10分钟内，甘油的保护产生了90％的solketal，苯甲醛的保护得到了95％的苯甲醛二甲基乙缩醛。仅用2.5mol％的HBA，在15秒内在UV辐射下苯甲醛二甲基乙缩醛的脱保护得到超过90％的苯甲醛产率。HBA还成功用于脱氧。发现溶剂在这些反应的HBA效率中起着重要作用。
• 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.