1,1,1-trifluorooct-3-yn-2-ol | 89524-13-0

• 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: 1,1,1-trifluorooct-3-yn-2-ol
• 英文别名: 1,1,1-trifluoro-3-octyn-2-ol
• CAS: 89524-13-0
• 化学式: C₈H₁₁F₃O
• 分子量: 180.17
• InChiKey: YIGWNBOZAOKETO-UHFFFAOYSA-N

物化性质

• 沸点：
  99-100 °C
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• 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：

  1,1,1-trifluorooct-3-yn-2-ol 在 二氯二茂钛 、 Isobutylmagnesium chloride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以60%的产率得到(Z)-1,1,1-Trifluoro-oct-3-en-2-ol
  参考文献：
  名称：

  由三氟乙醛和有机金属化合物制备三氟甲基化的烯丙醇

  摘要：

  通过使三氟乙醛与多种有机金属化合物反应，制备了许多在α-或γ-位带有三氟甲基的烯丙基醇，以及α-三氟甲基化的γ-烯醇和-ynol。大多数Reformatsky型或Grignard型反应都需要通过超声辐射来促进。

  DOI：

  10.1016/s0022-1139(00)83162-0
• 作为产物：
  描述：

  1-hexynyllithium 在 disodium hydrogenphosphate 、 potassium dihydrogenphosphate 、 starch 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 123.0h， 生成 1,1,1-trifluorooct-3-yn-2-ol
  参考文献：
  名称：

  A synthetic approach to seven-membered lactones by the microbial transformation of ynones having a trifluoromethyl group

  摘要：

  DOI：

  10.1016/s0022-1139(00)80888-x

文献信息

• Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones
  作者：Manickavasakam Ramasamy、Hui-Chang Lin、Sheng-Chu Kuo、Min-Tsang Hsieh

  DOI：10.1055/s-0037-1611694

  日期：2019.2

  A practical Lewis acid-catalyzed Meyer–Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivity in the synthesis of β-alkyl-β-fluoroalkyl-α,β-enones.

  开发了一种实用的路易斯酸催化 Meyer-Schuster 重排氟烷基化炔丙醇，产生一系列 β-氟烷基-α,β-烯酮。本文报道的方法在β-烷基-β-氟烷基-α,β-烯酮的合成中具有中等至高产率和高立体选择性。
• Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification
  作者：Sung-Jin Ko、Jung Yun Lim、Nan Young Jeon、Keehoon Won、Deok-Chan Ha、Bum Tae Kim、Hyuk Lee

  DOI：10.1016/j.tetasy.2009.03.041

  日期：2009.6

  In order to obtain optically active fluorinated propargyl alcohols, a lipase-catalyzed kinetic resolution has been carried out. The effect of lipase types, organic solvents, reaction temperature, and acyl donors was examined in the lipase-catalyzed transesterification of 1,1,1-trifluoro-4-phenyl-3-butyn-2-ol. Various enantiomerically pure fluorinated propargyl alcohols have been successfully prepared

  为了获得光学活性的氟化炔丙醇，已经进行了脂肪酶催化的动力学拆分。在脂肪酶催化的1,1,1-三氟-4-苯基-3-丁炔-2-醇的酯酶催化酯交换反应中研究了脂肪酶类型，有机溶剂，反应温度和酰基供体的影响。各种对映体纯的氟化炔丙基醇已在良好对映体过量（> 84％）已经成功地制备通过与丁酸乙烯酯的Novozym 435催化的酯交换在60℃下在Ñ正己烷。在某些情况下，对映体纯度极佳（> 99％ee）。
• Process for preparing a .beta.-(fluoroalkyl or
  申请人：Daikin Kogyo Co., Ltd.

  公开号：US04532020A1

  公开（公告）日：1985-07-30

  A process for preparing a .beta.-(fluoroalkyl or fluoroalkenyl)-.beta.-hydroxyalkyne represented by the formula ##STR1## wherein R.sub.f represents a fluoroalkyl or fluoroalkenyl group and R represents an aliphatic or aromatic group, comprising reacting an alkyne represented by the formula R--C.tbd.CH (II) wherein R is the same as defined above with a fluorine containing aldehyde represented by the formula R.sub.f CHO (III) wherein R.sub.f is the same as defined above in the presence of catalyst under ultrasonic irradiation. A process for preparing an .alpha.-(fluoroalkyl or fluoroalkenyl)allyl alcohol represented by the formula ##STR2## wherein R.sub.f represents a fluoroalkyl or fluoroalkenyl group, R represents an aliphatic or aromatic group and R' represents a hydrogen atom or an aliphatic group, comprising (1) reacting a .beta.-(fluoroalkyl or fluoroalkenyl)-.beta.-hydroxyalkyne represented by the formula ##STR3## wherein R.sub.f and R are respectively the same as defined above with a isobutylmagnesium halide represented by the formula i--C.sub.4 H.sub.9 MgX wherein X represents a halogen atom, and (2) reacting the reaction mixture thus obtained above with a halide represented by the formula R'X' wherein X' represents a halogen atom and R' is the same as defined above.

  一种制备β-(氟烷基或氟烯基)-β-羟基炔烃的方法，其化学式为##STR1## 其中，Rf代表氟烷基或氟烯基基团，R代表脂肪族或芳香族基团，包括在超声辐照下在催化剂存在下将化学式为R-C.tbd.CH (II)的炔烃与化学式为RfCHO (III)的含氟醛反应。一种制备α-(氟烷基或氟烯基)烯丙醇的方法，其化学式为##STR2## 其中Rf代表氟烷基或氟烯基基团，R代表脂肪族或芳香族基团，R'代表氢原子或脂肪基团，包括（1）将化学式为##STR3## 其中，Rf和R分别与上述定义相同的β-(氟烷基或氟烯基)-β-羟基炔烃与化学式为i-C4H9MgX的异丁基镁卤化物反应，其中X代表卤素原子，以及（2）将上述反应混合物与化学式为R'X'的卤化物反应，其中X'代表卤素原子，R'与上述定义相同。
• Process for preparing a beta-(fluoroalkyl or fluoroalkenyl)-beta-hydroxyalkyne and an alpha-(fluoroalkyl or fluoroalkenyl)-allyl alcohol thereof
  申请人：Daikin Kogyo Co., Ltd.

  公开号：EP0118890A1

  公开（公告）日：1984-09-19

  A process for preparing a β-(fluoroalkyl or fluoroalkenyl)-β-hydroxyalkyne represented by the formula wherein Rf represents a fluoroalkyl or fluoroalkenyl group and R represents an aliphatic or aromatic group, comprising reacting an alkyne represented by the formula wherein R is the same as defined above with a fluorine containing aldehyde represented by the formula wherein Rf is the same as defined above in the presence of catalyst under ultrasonic irradiation. A process for preparing an a-(fluoroalkyl or fluoroalkenyl) allyl alcohol represented by the formula ; wherein Rf represents a fluoroalkyl or fluoroalkenyl group, R represents an aliphatic or aromatic group and R' represents a hydrogen atom or an aliphatic group, comprising (1) reacting a β-(fluoroalkyl or fluoroalkenyl)-β-hydroxyalkyne represented by the formula wherein Rf and R are respectively the same as defined above with a isobutylmagnesium halide represented by the formula wherein X represents a halogen atom, and (2) reacting the reaction mixture thus obtained above with a halide represented by the formula wherein X' represents a halogen atom and R' is the same as defined above.

  一种制备β-(氟烷基或氟烯基)-β-羟基炔的工艺，由式表示 其中 Rf 代表氟烷基或氟烯基，R 代表脂肪族或芳香族基团，包括反应式如下代表的炔烃 式中 R 与上式定义相同的含氟醛反应 其中 Rf 与上述定义相同，在催化剂存在下，在超声波辐照下反应。 一种制备由式...代表的 a-(氟烷基或氟烯基)烯丙基醇的工艺； 其中 Rf 代表氟烷基或氟烯基，R 代表脂肪族或芳香族基团，R'代表氢原子或脂肪族基团，该工艺包括 (1) 反应式中β-(氟烷基或氟烯基)-β-羟基炔 其中 Rf 和 R 分别与上式所定义的异丁基卤化镁相同 式中 X 代表卤素原子，以及 (2) 将上述反应混合物与式中代表的卤化物反应 其中 X'代表卤素原子，R'与上述定义相同。
• Addition of organocuprates to acetylenic di- and trifluoromethyl ketones. Regiospecific synthesis of .beta.,.beta.-disubstituted unsaturated fluoro ketones
  作者：Russell J. Linderman、Madhu S. Lonikar

  DOI：10.1021/jo00261a006

  日期：1988.12