α,α,3-Trimethyloxiranemethanol | 1193-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,α,3-Trimethyloxiranemethanol
• 英文别名: 1-(Dimethylhydroxymethyl)-1-methyloxiran；2-(3-methyl-oxiranyl)-propan-2-ol；2-(3-Methyloxiran-2-yl)propan-2-ol
• CAS: 1193-04-0
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: REBJJHOONXCNHP-UHFFFAOYSA-N

物化性质

• 沸点：
  163.3±8.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-2-戊烯 以42%的产率得到
  参考文献：
  名称：

  ADAM W.; GRIESBECK A.; STAAB E., TETRAHEDRON LETT., 27,(1986) N 25, 2839-2842

  摘要：

  DOI：

文献信息

• A convenient “one-pot” synthesis of epoxy alcohols via photooxygenation of olefins in the presence of titanium(IV) catalyst
  作者：Waldemar Adam、Axel Griesbeck、Eugen Staab

  DOI：10.1016/s0040-4039(00)84656-0

  日期：1986.1

  The ene reaction of singlet oxygen with alkenes in the presence of titanium alkoxides was employed to prepare epoxy alcohols in high diastereoselectivity; enantioselectivity could be achieved by use of diethyl tartrate as chiral auxiliary.

  在烷氧基钛存在下，单线态氧与烯烃的烯反应用于高非对映选择性地制备环氧醇。对映选择性可以通过使用酒石酸二乙酯作为手性助剂来实现。
• Photooxygenation of olefins in the presence of titanium(IV) catalyst. A convienient "one-pot" synthesis of epoxy alcohols.
  作者：Waldemar Adam、Martin Braun、Axel Griesbeck、Vittorio Lucchini、Eugen Staab、Bernd Will

  DOI：10.1021/ja00183a032

  日期：1989.1
• Diastereoselective Catalytic Epoxidation of Chiral Allylic Alcohols by the TS-1 and Ti-β Zeolites:  Evidence for a Hydrogen-Bonded, Peroxy-Type Loaded Complex as Oxidizing Species
  作者：Waldemar Adam、Avelino Corma、T. Indrasena Reddy、Michael Renz

  DOI：10.1021/jo970364i

  日期：1997.5.1

  The similar diastereoselectivities as for peracids implicate a pentacoordinated metal peroxy species in the epoxidation of chiral allylic alcohols by the titanium-containing zeolites TS-1 and Ti-beta. In the loaded complex, the allylic alcohol substrate is fixed through hydrogen bonding to the metal center, with A(1,3) strain as the dominant conformational feature. By comparison of the diastereoselectivities to those for VO(acac)(2)/t-BuOOH, we exclude a peroxy-type complex with direct coordination of the allylic alcohol to the titanium center by means of metal-alcoholate bonding. Neither does a peroxo-type titanium complex apply, as confirmed by comparing the diastereoselectivities with those observed for dioxiranes. With the help of tert-butyl-substituted allylic alcohols as substrates, which are not epoxidized by the TS-1 but by the Ti-beta catalyst, it was unequivocally confirmed that the oxidation occurs inside of the zeolite and not on the outer surface.
• Adam, Waldemar; Kumar, Rajiv; Reddy, T. Indrasena, Angewandte Chemie, 1996, vol. 108, # 8, p. 944 - 947
  作者：Adam, Waldemar、Kumar, Rajiv、Reddy, T. Indrasena、Renz, Michael

  DOI：——

  日期：——
• TISHCHENKO I. G.; BUBEL O. N.; STASEVICH G. Z., VESTSI AN BSSR. CEP. XIM. N., IZV. AN BSSR. CEP. XIM. N., 1979, HO 1, 89-+
  作者：TISHCHENKO I. G.、 BUBEL O. N.、 STASEVICH G. Z.

  DOI：——

  日期：——