1-methoxy-1-trimethylsilyloxy-2-phenylcyclopropane | 123169-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methoxy-1-trimethylsilyloxy-2-phenylcyclopropane
• 英文别名: (1-Methoxy-2-phenylcyclopropyl)oxy-trimethylsilane
• CAS: 123169-65-3
• 化学式: C₁₃H₂₀O₂Si
• 分子量: 236.386
• InChiKey: FFZIKOBEZMURKT-UHFFFAOYSA-N

物化性质

• 沸点：
  262.6±40.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methoxy-1-trimethylsilyloxy-2-phenylcyclopropane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 1,2-二乙氧基-1,2-二(三甲基硅氧基)环丙烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以54%的产率得到Methyl cinnamate
  参考文献：
  名称：

  从四氧取代环丙烷到受体的连续双电子转移

  摘要：

  DOI：

  10.1021/ja992397g
• 作为产物：
  描述：

  苯乙酸甲酯 在 diethylzinc 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.5h， 生成 1-methoxy-1-trimethylsilyloxy-2-phenylcyclopropane
  参考文献：
  名称：

  对映选择性铜催化环丙醇和环丙酮酮缩醛的自由基开环氰化

  摘要：

  通过铜催化的自由基中继过程，开发了一种新的环丙醇及其衍生物的对映选择性氰化方法。各种环丙醇和环丙酮缩醛均与催化条件兼容，从而为β-羰基腈提供了出色的对映选择性。这些产品可以很容易地转化为手性γ-氨基酸衍生物和药物，例如（R）-baclofen。初步的机理研究支持了环丙氧基自由基的开环过程，随后是铜催化的苄基自由基的对映选择性氰化，以对映选择性的方式形成C-CN键。

  DOI：

  10.1002/adsc.202000202

文献信息

• An improved synthesis of substituted cyclopropanone acetals and hemiacetals
  作者：G. Rousseau、N. Slougui

  DOI：10.1016/s0040-4039(00)81627-5

  日期：1983.1

  Cyclopropanation of ketene alkylsilylacetals or ketene disilylacetals with diethylzinc-methylene iodide leads to cyclopropanone acetals in high yield, and after methanolysis to cyclopropanone hemiacetals or hydrates.

  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。
• 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.
• Preparation of .beta.-amino esters from ethyl azidoformate and 1-alkoxy-1-siloxycyclopropanes
  作者：Michiharu Mitani、Osamu Tachizawa、Hiroshi Takeuchi、Kikuhiko Koyama

  DOI：10.1021/jo00283a045

  日期：1989.10
• MITANI, MICHIHARU;TACHIZAWA, OSAMU;TAKEUCHI, HIROSHI KOYAMA KIKUHIKO, J. ORG. CHEM., 54,(1989) N2, C. 5397-5399
  作者：MITANI, MICHIHARU、TACHIZAWA, OSAMU、TAKEUCHI, HIROSHI KOYAMA KIKUHIKO

  DOI：——

  日期：——