2-(5-Prop-2-enoxypentoxy)oxane | 146444-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(5-Prop-2-enoxypentoxy)oxane
• CAS: 146444-93-1
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: BAUUAKHHFINMEW-UHFFFAOYSA-N

物化性质

• 沸点：
  314.6±42.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  2-(5-Prop-2-enoxypentoxy)oxane 在 1,3-丙二硫醇 、 cerium(III) chloride 、 sodium iodide 作用下， 以 硝基甲烷 为溶剂， 反应 24.0h， 以80%的产率得到1,5-戊二醇
  参考文献：
  名称：

  Cerium-Mediated Deprotection of Substituted Allyl Ethers

  摘要：

  在有烯丙基碘清除剂存在的情况下，在回流的硝基甲烷中使用 CeCl3 - 7 H2O/NaI 系统可以从醇中去除取代的烯丙基保护基团。与此相反，烯丙基的脱保护作用在乙腈中几乎无法进行。

  DOI：

  10.1055/s-2001-18746
• 作为产物：
  描述：

  5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol 、 3-溴丙烯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(5-Prop-2-enoxypentoxy)oxane
  参考文献：
  名称：

  Facile and Selective Deallylation of Allyl Ethers Using Diphosphinidenecyclobutene-Coordinated Palladium Catalysts

  摘要：

  (pi-Allyl)palladium triflate bearing a 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-tert-butylphenylphosphinidene)cyclobutene ligand (DPCB-OMe), [Pd(eta(3)-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes deallylation of a variety of allyl ethers in aniline to give corresponding alcohols in high yields under mild conditions. The reactions can be performed in air without loss of a variety of functionalities including vinyl, alkynyl, hydroxy, acetoxy, silyloxy, and acetal groups. Allyl 2-allyloxybenzoate selectively undergoes deallylation of the allyloxy group to give allyl salicylate in quantitative yield.

  DOI：

  10.1021/jo049732q

文献信息

• Facile and selective cleavage of allyl ethers, amines and esters using polymethylhydrosiloxane–ZnCl 2 /Pd(PPh 3 ) 4
  作者：S Chandrasekhar、Ch Raji Reddy、R Jagadeeshwar Rao

  DOI：10.1016/s0040-4020(01)00187-9

  日期：2001.4

  Allyl deprotection to liberate free hydroxy, amino and acid groups from the corresponding allyl ethers, amines and esters is achieved under mild conditions. The reagent combination employed for this transformation is polymethylhydrosiloxane (PMHS), ZnCl2 and Pd(PPh3)4.

  在温和条件下实现烯基脱保护以从相应的烯丙基醚，胺和酯中释放出游离的羟基，氨基和酸基。用于该转化的试剂组合是聚甲基氢硅氧烷（PMHS），ZnCl 2和Pd（PPh 3）4。
• An efficient and selective deprotection of allyl ethers by a CeCl3.7H2O NaI system
  作者：R.Mathew Thomas、G.Sudhakar Reddy、D.S. Iyengar

  DOI：10.1016/s0040-4039(99)01575-0

  日期：1999.10

  A mild, novel and chemoselective method for the deprotection of allyl ethers by a CeCl3.7H2O NaI system is described.

  描述了一种温和，新颖和化学选择性的方法，用于通过CeCl 3 .7H 2 O 3 NaI系统对烯丙基醚进行脱保护。
• Practical zirconium-mediated deprotective method of allyl groups
  作者：Hisanaka Ito、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1021/jo00055a041

  日期：1993.1
• Yang, Seung Gak; Park, Min Young; Kim, Yong Hae, Synlett, 2002, # 3, p. 492 - 494
  作者：Yang, Seung Gak、Park, Min Young、Kim, Yong Hae

  DOI：——

  日期：——
• Facile and Selective Deallylation of Allyl Ethers Using Diphosphinidenecyclobutene-Coordinated Palladium Catalysts
  作者：Hiromi Murakami、Tatsuya Minami、Fumiyuki Ozawa

  DOI：10.1021/jo049732q

  日期：2004.6.1

  (pi-Allyl)palladium triflate bearing a 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-tert-butylphenylphosphinidene)cyclobutene ligand (DPCB-OMe), [Pd(eta(3)-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes deallylation of a variety of allyl ethers in aniline to give corresponding alcohols in high yields under mild conditions. The reactions can be performed in air without loss of a variety of functionalities including vinyl, alkynyl, hydroxy, acetoxy, silyloxy, and acetal groups. Allyl 2-allyloxybenzoate selectively undergoes deallylation of the allyloxy group to give allyl salicylate in quantitative yield.