bis(1,3-dihydroisobenzofuran-1-yl)peroxide | 4676-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: bis(1,3-dihydroisobenzofuran-1-yl)peroxide
• 英文别名: 1,1'-peroxibis(1,3-dihydroisobenzofuran)；bis-(1,3-dihydro-isobenzofuran-1-yl)-peroxide；di-phthalan-1-yl peroxide；Di-phthalan-1-yl-peroxid；Diphthalanyl-peroxid
• CAS: 4676-86-2
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: RCTQBTVRSYAVIW-UHFFFAOYSA-N

物化性质

• 沸点：
  419.8±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis(1,3-dihydroisobenzofuran-1-yl)peroxide 在 [FeL1(THF)(OTf)₂] 作用下， 以 苯 为溶剂， 生成 苯酞
  参考文献：
  名称：

  Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst

  摘要：

  Selective alpha-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective alpha-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O-2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H-2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O-2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H-2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.

  DOI：

  10.1021/ja502167h
• 作为产物：
  描述：

  1,3-二氢异苯并呋喃 在 iron(II) triflate 、 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine 、 氧气 作用下， 以 苯 为溶剂， 42.0 ℃ 、101.33 kPa 条件下， 以9%的产率得到bis(1,3-dihydroisobenzofuran-1-yl)peroxide
  参考文献：
  名称：

  Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst

  摘要：

  Selective alpha-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective alpha-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O-2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H-2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O-2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H-2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.

  DOI：

  10.1021/ja502167h

文献信息

• Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
  作者：Katsuhiro Isozaki、Tomoya Yokoi、Ryota Yoshida、Kazuki Ogata、Daisuke Hashizume、Nobuhiro Yasuda、Koichiro Sadakane、Hikaru Takaya、Masaharu Nakamura

  DOI：10.1002/asia.201600045

  日期：2016.4.5

  scaffolds against acidic/basic, oxidizing, and high‐temperature conditions enabled us to perform selective transformations of the N‐Boc and C−OMe termini into various functional groups, such as alkyl amide, alkyl urea, and polyether groups, without the loss of the Ru center or enantiomeric purity. The resulting dialkylated Ru‐bound norvaline, n‐C11H23CO−l‐[Ru(pydc)(terpy)]Nva−NH‐n‐C11H23 (l‐4) was found to

  两个（ONO钳形）钌络合物结合的正缬氨酸，Boc−[Ru(pydc)(terpy)]Nva−OMe ( 1 ; Boc=叔丁氧基羰基，terpy=三联吡啶基，Nva=正缬氨酸)和Boc−[Ru(pydc) )( t Bu‐terpy)]Nva−OMe ( 5 ) 已成功合成，并且通过单晶 X 射线衍射明确确定了它们的分子结构和绝对构型。钳式 Ru 配合物和正缬氨酸支架对酸性/碱性、氧化和高温条件的鲁棒性使我们能够将 N -Boc和C -OMe 末端选择性转化为各种官能团，例如烷基酰胺、烷基脲和聚醚基团，而不损失 Ru 中心或对映体纯度。所得二烷基化 Ru 结合正缬氨酸n ‐C 11 H 23 CO− l ‐[Ru(pydc)(terpy)]Nva−NH‐ n ‐C 11 H 23 ( l ‐ 4 ) 被发现具有优异的自组装性有机溶剂中的性质，从而提供相应的超分子凝胶。Ru 结合的正缬氨酸l
• The Nature of Oxygen in Coal: Preparation and Properties of Phthalan¹
  作者：Jacob Entel、Clarence H. Ruof、H. C. Howard

  DOI：10.1021/ja01122a048

  日期：1952.1
• Rearrangement of diphenan to 9, 10-dihydro-9-phenanthrol by potassium amide and dehydration to phenanthrene. Results with 1, 8-naphthalan, phthalan, and 2, 5-dihydrofuran
  作者：Alfred J. Weinheimer、Simon W. Kantor、Charles R. Hauser

  DOI：10.1021/jo50013a004

  日期：1953.7
• Weinheimer et al., Journal of Organic Chemistry, 18 <1953 801, 804
  作者：Weinheimer et al.

  DOI：——

  日期：——