3-phenylcyclohexene oxide | 20383-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3-phenylcyclohexene oxide
• 英文别名: 2,3-Epoxy-1-phenyl-cyclohexan；1,2-epoxy-3-phenyl-cyclohexane；2-Phenyl-7-oxabicyclo[4.1.0]heptane
• CAS: 20383-30-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: GEPRMIFUDKPNLD-UHFFFAOYSA-N

物化性质

• 沸点：
  276.1±9.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenylcyclohexene oxide 生成 6-phenyl-2-cyclohexen-1-ol
  参考文献：
  名称：

  Mandrou,A.-M. et al., Bulletin de la Societe Chimique de France, 1962, p. 1546 - 1554

  摘要：

  DOI：
• 作为产物：
  描述：

  3-phenyl-1-cyclohexene 在 Ru(2,2':6',2''-terpyridine)(2,6-pyridinedicarboxylate) 双氧水 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 12.0h， 以83%的产率得到3-phenylcyclohexene oxide
  参考文献：
  名称：

  使用过氧化氢水溶液进行烯烃环氧化的简便方法。

  摘要：

  [反应：见正文]配合物[Ru（tpy）（pydic）]（1a）是一种活性催化剂，可通过叔醇中30％的过氧化氢水溶液将烯烃环氧化。该方案易于操作，并以良好或优异的收率得到相应的环氧化物。已合成手性对映纯[Ru（tpy）（pydic）]配合物，并成功地用于该程序。

  DOI：

  10.1021/ol047604i

文献信息

• Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)
  作者：Gary A. Rogers、Stanley M. Parsons、D. C. Anderson、Lena M. Nilsson、Ben A. Bahr、Wayne D. Kornreich、Rose Kaufman、Robert S. Jacobs、Bernard Kirtman

  DOI：10.1021/jm00126a013

  日期：1989.6

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.
• Convenient Method for Epoxidation of Alkenes Using Aqueous Hydrogen Peroxide
  作者：Man Kin Tse、Markus Klawonn、Santosh Bhor、Christian Döbler、Gopinathan Anilkumar、Herbert Hugl、Wolfgang Mägerlein、Matthias Beller

  DOI：10.1021/ol047604i

  日期：2005.3.1

  [reaction: see text] The complex [Ru(tpy)(pydic)] (1a) is an active catalyst for epoxidation of alkenes by aqueous 30% hydrogen peroxide in tertiary alcohols. The protocol is simple to operate and gives the corresponding epoxides in good to excellent yields. Chiral enantiopure [Ru(tpy)(pydic)] complexes have been synthesized and successfully applied in this procedure.

  [反应：见正文]配合物[Ru（tpy）（pydic）]（1a）是一种活性催化剂，可通过叔醇中30％的过氧化氢水溶液将烯烃环氧化。该方案易于操作，并以良好或优异的收率得到相应的环氧化物。已合成手性对映纯[Ru（tpy）（pydic）]配合物，并成功地用于该程序。
• Mandrou,A.-M. et al., Bulletin de la Societe Chimique de France, 1962, p. 1546 - 1554
  作者：Mandrou,A.-M. et al.

  DOI：——

  日期：——