1-甲氧基-2-苯基环丙烷-1-醇 | 56955-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-甲氧基-2-苯基环丙烷-1-醇
• 英文名称: 1-methoxy-2-phenylcyclopropanol
• 英文别名: 2-Phenylcyclopropanon-methyl-hemiacetal；Cyclopropanol, 1-methoxy-2-phenyl-；1-methoxy-2-phenylcyclopropan-1-ol
• CAS: 56955-33-0
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: UUFYKYURZWRSFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  263.1±40.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  1-甲氧基-2-苯基环丙烷-1-醇 在 四氯苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到Methyl cinnamate
  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
• 作为产物：
  描述：

  (1-methoxy-2-phenylvinyloxy)trimethylsilane 在 三甲基氯硅烷 、 diethylzinc 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 1-甲氧基-2-苯基环丙烷-1-醇
  参考文献：
  名称：

  取代环丙烷丙酮缩醛和半缩醛的合成方法改进

  摘要：

  乙烯酮烷基甲硅烷基缩醛或乙烯酮二甲硅烷基缩醛与二乙基锌-亚甲基碘的环丙烷化可高产率产生环丙烷缩醛，并且在甲醇水解后生成环丙烷酮半缩醛或水合物。

  DOI：

  10.1016/s0040-4039(00)81627-5

文献信息

• Ring-opening addition reaction of cyclopropanol derivatives with carbenes
  作者：Akira Oku、Masaharu Iwamoto、Kenji Sanada、Manabu Abe

  DOI：10.1016/s0040-4039(00)60864-x

  日期：1992.11

  Chloro(phenyl)carbene and diphenylcarbene reacted with cyclopropanone hemiacetals, cyclopropanols, and cyclopropanone cyanohydrins to give 4-phenylbutanoic acid derivatives. The mechanism was explained in terms of a homolytic process that the O-H group of cyclopropanols reacted as a formal H donor with carbenes.

  氯（苯基）卡宾和二苯卡宾与环丙烷酮半缩醛，环丙醇和环丙烷酮氰醇反应生成4-苯基丁酸衍生物。根据均相分解过程解释了该机理，其中环丙醇的OH基团作为正式的H供体与碳烯反应。
• Bakker,B.H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1975, vol. 94, p. 64 - 69
  作者：Bakker,B.H. et al.

  DOI：——

  日期：——
• Bakker,B.H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1976, vol. 95, p. 274 - 277
  作者：Bakker,B.H. et al.

  DOI：——

  日期：——
• ROUSSEAU, G.;SLOUGUI, N., TETRAHEDRON LETT., 1983, 24, N 12, 1251-1254
  作者：ROUSSEAU, G.、SLOUGUI, N.

  DOI：——

  日期：——
• BAKKER B. H.; VAN RAMESDONK H. J.; STEINBERG H.; DE BOER T. J., REC. TRAV. CHIM. <RTCP-A3>, 1975, 94, NO 3, 64-69
  作者：BAKKER B. H.、 VAN RAMESDONK H. J.、 STEINBERG H.、 DE BOER T. J.

  DOI：——

  日期：——