1-Methoxy-1-(trimethylsiloxy)-2-(4-methoxyphenyl)cyclopropane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Methoxy-1-(trimethylsiloxy)-2-(4-methoxyphenyl)cyclopropane
• 英文别名: [1-methoxy-2-(4-methoxyphenyl)cyclopropyl]oxy-trimethylsilane
• 化学式: C₁₄H₂₂O₃Si
• 分子量: 266.412
• InChiKey: CTOXDYKTSRZSLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Methoxy-1-(trimethylsiloxy)-2-(4-methoxyphenyl)cyclopropane 在 三甲基氯硅烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.16h， 生成 Methyl 1-(4-methoxyphenyl)-4,4,5,5-tetracyanopentanoate
  参考文献：
  名称：

  Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone

  摘要：

  The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron accepters (TCNE, DDQ, chloranil, and 1-cyanonaphthalene). With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e. With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6. In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated. With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occurred. The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors. The mechanism of the reaction with quinones, in particular, was investigated in detail.

  DOI：

  10.1021/jo00103a043

文献信息

• Photoinduced electron transfer reaction of cyclopropanone acetals with arylmethyl methanesulfonate: generation of β-keto radical species and application to C–C bond formation
  作者：Manabu Abe、Akira Oku

  DOI：10.1039/c39940001673

  日期：——

  The photoinduced electron transfer reaction of the cyclopropanone acetals 1 with arylmethyl methanesulfonates 4 or 10 as electron acceptors was found to generate a transient pair of radicals, the β-keto radical 3 and the arylmethyl radical, which underwent a novel carbon–carbon bond formation reaction at the sterically hindered β-position of the esters.

  研究发现，环丙酮缩醛 1 与作为电子受体的芳基甲基甲烷磺酸盐 4 或 10 发生光诱导电子转移反应时，会产生一对瞬时自由基--δ-酮自由基 3 和芳基甲基自由基，这对自由基在酯的立体受阻δ位上发生了新的碳碳键形成反应。
• Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone
  作者：Akira Oku、Manabu Abe、Masaharu Iwamoto

  DOI：10.1021/jo00103a043

  日期：1994.12

  The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron accepters (TCNE, DDQ, chloranil, and 1-cyanonaphthalene). With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e. With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6. In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated. With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occurred. The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors. The mechanism of the reaction with quinones, in particular, was investigated in detail.