3-(2,2,2-trifluoro-1-hydroxyethyl)cyclohexene | 19687-12-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 3-(2,2,2-trifluoro-1-hydroxyethyl)cyclohexene
• 英文别名: 1-Cyclohex-2-en-1-yl-2,2,2-trifluoroethanol
• CAS: 19687-12-8
• 化学式: C₈H₁₁F₃O
• 分子量: 180.17
• InChiKey: NGARCKIGFUUMCR-UHFFFAOYSA-N

物化性质

• 沸点：
  211.6±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,2,2-trifluoro-1-hydroxyethyl)cyclohexene 、 3-溴环己烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 以41%的产率得到3-[1-(cyclohex-2-enyl-1-yloxy)-2,2,2-trifluoroethyl]cyclohexene
  参考文献：
  名称：

  Towards the Syntheses of α-Trifluoromethylated Oxygenated Heterocycles and Their Precursors

  摘要：

  从三氟乙醛缩甲醛出发，通过经典的环化反应合成各种α-三氟甲基化氧杂环的可能性已被证明。通过这种方式，可以轻松地通过环加成反应获得具有氧α位的CF3基团的六元环状化合物、δ-内酯以及大环内酯。双环化合物也可以通过分子内Pauson-Khand反应来合成。

  DOI：

  10.1055/s-2005-872076
• 作为产物：
  描述：

  2,2,2-三氟乙醛 、 环己烯 在 三氯化铁 作用下， 生成 3-(2,2,2-trifluoro-1-hydroxyethyl)cyclohexene
  参考文献：
  名称：

  Pautrat,R. et al., Bulletin de la Societe Chimique de France, 1968, p. 1182 - 1186

  摘要：

  DOI：

文献信息

• Studies on Trifluoromethyl Ketones. VII. Ene Reaction of Trifluroacetaldehyde and Its Application for Synthesis of Trifluoromethyl Compounds.
  作者：Keizo OGAWA、Takabumi NAGAI、Masahiko NONOMURA、Toshiyuki TAKAGI、Mayumi KOYAMA、Akira ANDO、Takuichi MIKI、Itsumaro KUMADAKI

  DOI：10.1248/cpb.39.1707

  日期：——

  As an extension of our studies on the ene reaction of trifluoromethyl ketones, the ene reaction of trifluoroacetaldehyde was examined. The aldehyde reacted with various ene compounds as a good enophile in the presence of Lewis acids, among which methylaluminum dichloride workded best, though polymerization of the aldehyde caused by the Lewis acid among which methylaluminum dichloride worked best, though polymerization of the aldehyde caused by the Lewis acid often lowered the isolation yields of the ene reaction. The ene reaction products were successfully oxidized to trifluoromethyl β, γ-unsaturated ketones with Dess Martin reagent. Reduction of the ene reaction products followed by oxidation with Jones reagent gave saturated trifluoromethyl ketones. The β, γ-unsaturated ketone rearranged on thermolysis to an α, β-unsaturated ketone. These ketones obtained were converted to otehr types of trifluoromethyl compounds. Thus, the ene reaction of trifluoroacetaldehyde provides a versatile method for synthesis of many types of trifluoromethyl compounds. During this derivatization, a trifluoromethyl group was found to behave as a much larger substituent than a decyl group.

  作为三氟甲基酮烯化反应研究的延伸，我们还研究了三氟乙醛的烯化反应。在路易斯酸（其中二氯化甲基铝的效果最好）存在的情况下，该醛作为一种良好的亲烯烃与各种烯化合物发生反应，但路易斯酸引起的醛聚合往往会降低烯反应的分离产率。使用 Dess Martin 试剂成功地将烯酮反应产物氧化为三氟甲基 β、γ-不饱和酮。烯反应产物还原后再用琼斯试剂氧化，得到饱和的三氟甲基酮。β、γ-不饱和酮在热分解过程中重新排列为 α、β-不饱和酮。得到的这些酮又转化为其他类型的三氟甲基化合物。因此，三氟乙醛的烯化反应为合成多种类型的三氟甲基化合物提供了一种通用方法。在这一衍生过程中，发现三氟甲基的取代基比癸基大得多。
• Ene-type reaction of trifluoroacetaldehyde hemiacetal with ene compounds in the presence of a Lewis acid
  作者：Kunihiro Sakumo、Noriko Kuki、Terumi Kuno、Toshiyuki Takagi、Mayumi Koyama、Akira Ando、Itsumaro Kumadaki

  DOI：10.1016/s0022-1139(98)00291-7

  日期：1999.2

  Reaction of trifluoroacetaldehyde ethyl hemiacetal with ene compounds in the presence of a Lewis acid gives a-trifluoromethylated homoallyl alcohols, the same products as those from the ene reaction of trifluoroacetaldehyde, in moderate to good yields. Boron trifluoride etherate was found to be most effective in this reaction. This method eliminated many difficulties encountered on the ene reaction of trifluoroacetaldehyde, which is a gas at room temperature and polymerizes to insoluble polymer in the presence of a Lewis acid. (C) 1999 Elsevier Science S.A. All rights reserved.
• NAGAI, TAKABUMI;NISHIOKA, GORO;KOYAMA, MAYUMI;ANDO, AKIRA;MIKI, TAKUICHI;+, CHEM. AND PHARM. BULL., 30,(1991) N, C. 233-235
  作者：NAGAI, TAKABUMI、NISHIOKA, GORO、KOYAMA, MAYUMI、ANDO, AKIRA、MIKI, TAKUICHI、+

  DOI：——

  日期：——