(2E)-1,1-二甲基-5-甲亚基庚-2,6-二烯-1-基过氧化氢 | 109789-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氢过氧化物
• 中文名称: (2E)-1,1-二甲基-5-甲亚基庚-2,6-二烯-1-基过氧化氢
• 英文名称: 1,1-dimethyl-5-methylene-2,6-heptadienyl hydroperoxide
• 英文别名: 6-hydroperoxy-7-methyl-5-methylene-1,7-octadiene；(5E)-7-Hydroperoxy-7-methyl-3-methylideneocta-1,5-diene
• CAS: 109789-13-1
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: FUIFIERPDQXBRC-SOFGYWHQSA-N

物化性质

• 沸点：
  274.5±29.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-1,1-二甲基-5-甲亚基庚-2,6-二烯-1-基过氧化氢 在 oxygen 、 tetraphenylporphyrin 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以45%的产率得到4-[(E)-4-hydroperoxy-4-methylpent-2-enyl]-3,6-dihydro-1,2-dioxine
  参考文献：
  名称：

  无环共轭二烯的敏化光氧合

  摘要：

  研究了多种无环1,3-二烯的敏化光氧合。单线态氧在无环共轭二烯上的1,4-环加成反应与立体特异性的热Diels-Alder反应以及取代基的空间和电子效应密切相关。单线态氧对共轭二烯和分离的CC双键的反应顺序如下：三取代单烯烃> 2-取代的1,3-二烯>二取代单烯烃。

  DOI：

  10.1016/s0040-4020(01)96586-x
• 作为产物：
  描述：

  月桂烯 在 C₆₀(H)CH₂SiMe₂(OCH₂CH₂C₈F₁₇) 、 氧气 作用下， 以 六氟苯 为溶剂， 反应 0.5h， 以47%的产率得到(2E)-1,1-二甲基-5-甲亚基庚-2,6-二烯-1-基过氧化氢
  参考文献：
  名称：

  Efficient Photooxygenation of Olefins by a C₆₀Derivative Bearing an Organofluorine Tail

  摘要：

  一种通过二甲基硅基部分连接有有机氟尾的C60衍生物（1）被证明在C6F6中是一种高效的光敏剂。在常温下，在氧气氛围下，1以0.5–1.5 mol%的催化剂成功实现了烯烃或二烯的光氧化反应。

  DOI：

  10.1246/cl.1999.469

文献信息

• Approaches to Stereoselective Dioxygenation of Alkenes:  Chiral Phosphite Ozonides
  作者：Patrick H. Dussault、Kevin R. Woller

  DOI：10.1021/jo961564h

  日期：1997.3.1
• Synthetic Chemistry with Fullerenes. Photooxygenation of Olefins
  作者：Hidetoshi Tokuyama、Eiichi Nakamura

  DOI：10.1021/jo00084a036

  日期：1994.3

  Under irradiation with visible or UV (>290 nm) light in the presence of molecular oxygen and a minute amount of fullerenes, olefins and dienes undergo ene and Diels-Alder reactions with singlet oxygen to give photooxygenation products. The regio- and stereoselectivities of the photooxygenation of beta-myrcene, (+)-pulegone, 4-methylpent-3-en-2-ol, and (+)-limonene were very similar to those observed in known singlet oxygen reactions, indicating that the fullerene-sensitized reaction generates free singlet oxygen. The efficiency of fullerenes and conventional sensitizers was qualitatively examined by using the Diels-Alder reaction between O-1(2) and furan-2-carboxylic acid as a probe. Among those examined, C-70 was found to be the most effective. The reaction was the fastest and completed with as little as 0.0001 equiv of C-70. C-60 and hematoporphyrin were found to be of similar efficiency. The methanofullerene 13, which lacks one olefinic conjugation in the C-60 core, was as good as C60 itself, but the aminofullerene 14, lacking six double bonds, was quite inferior. The fullerene carboxylic acid 15, which was previously shown to show considerable biochemical activity, was found to be capable of generating singlet oxygen in aqueous DMSO.
• MATSUMOTO, MASAKATSU;DOBASHI, SATOSHI;KURODA, KEIKO;KONDO, KIYOSI, TETRAHEDRON, 1985, 41, N 11, 2147-2154
  作者：MATSUMOTO, MASAKATSU、DOBASHI, SATOSHI、KURODA, KEIKO、KONDO, KIYOSI

  DOI：——

  日期：——
• Sensitized photo-oxygenation of acyclic conjugated dienes
  作者：Masakatsu Matsumoto、Satoshi Dobashi、Keiko Kuroda、Kiyosi Kondo

  DOI：10.1016/s0040-4020(01)96586-x

  日期：1985.1

  Sensitized photo-oxygenation of a wide variety of acyclic 1,3-dienes was investigated. The 1,4-cycloaddition of singlet oxygen to acyclic conjugated dienes was closely related to the thermal Diels-Alder reaction in stereospecificity, and steric and electronic effects of substituents. Reactivity order of singlet oxygen toward conjugated dienes and isolated C—C double bonds was exhibited as follows:

  研究了多种无环1,3-二烯的敏化光氧合。单线态氧在无环共轭二烯上的1,4-环加成反应与立体特异性的热Diels-Alder反应以及取代基的空间和电子效应密切相关。单线态氧对共轭二烯和分离的CC双键的反应顺序如下：三取代单烯烃> 2-取代的1,3-二烯>二取代单烯烃。
• Efficient Photooxygenation of Olefins by a C₆₀Derivative Bearing an Organofluorine Tail
  作者：Hideo Nagashima、Koji Hosoda、Tomoaki Abe、Shoichi Iwamatsu、Takaaki Sonoda

  DOI：10.1246/cl.1999.469

  日期：1999.6

  A C60 derivative bearing an organofluorine tail through the dimethylsilyl moiety (1) was proved to be an efficient photosensitizer in C6F6. Photooxygenation of olefins or dienes was accomplished by catalysis of 1 (0.5–1.5 mol%) at room temperature under an oxygen atmosphere.

  一种通过二甲基硅基部分连接有有机氟尾的C60衍生物（1）被证明在C6F6中是一种高效的光敏剂。在常温下，在氧气氛围下，1以0.5–1.5 mol%的催化剂成功实现了烯烃或二烯的光氧化反应。