(Z)-1,1,1-Trifluoro-2-hydroxy-4-phenyl-3-butene | 89524-14-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-1,1,1-Trifluoro-2-hydroxy-4-phenyl-3-butene
• 英文别名: (Z)-1-phenyl-3-hydroxy-4,4,4-trifluoro-1-butene；(Z)-1,1,1-trifluoro-4-phenyl-3-buten-2-ol；(Z)-1,1,1-trifluoro-4-phenyl-3-butene-2-ol；(Z)-1,1,1-trifluoro-4-phenylbut-3-en-2-ol
• CAS: 89524-14-1
• 化学式: C₁₀H₉F₃O
• 分子量: 202.176
• InChiKey: TWENPNDYVIPCRK-SREVYHEPSA-N

物化性质

• 沸点：
  78-80 °C(Press: 3 Torr)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (Z)-1,1,1-Trifluoro-2-hydroxy-4-phenyl-3-butene 在 platinum(IV) oxide 、 lipase-MY (Candida cylindracea) 吡啶 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 1,1,1-三氟-4-苯基-2-丁醇
  参考文献：
  名称：

  具有三氟甲基的烯丙基醇的立体异构体的合成方法

  摘要：

  具有三氟甲基的光学纯的烯丙基醇的许多立体异构体[CF 3 CH（OH）CH ＝ CHR：R ＝ Ph。利用水解酶的乙酸盐的不对称水解的对映体特异性，制备了C 6 H 13 ]。确定了它们的绝对构型。

  DOI：

  10.1016/s0022-1139(00)82938-3
• 作为产物：
  描述：

  1,1,1-trifluoro-4-phenylbut-3-yn-2-ol 在 Lindlar's catalyst 氢气 作用下， 以 正己烷 为溶剂， 反应 3.0h， 生成 (Z)-1,1,1-Trifluoro-2-hydroxy-4-phenyl-3-butene
  参考文献：
  名称：

  具有三氟甲基的烯丙基醇的立体异构体的合成方法

  摘要：

  具有三氟甲基的光学纯的烯丙基醇的许多立体异构体[CF 3 CH（OH）CH ＝ CHR：R ＝ Ph。利用水解酶的乙酸盐的不对称水解的对映体特异性，制备了C 6 H 13 ]。确定了它们的绝对构型。

  DOI：

  10.1016/s0022-1139(00)82938-3

文献信息

• Synthesis of allylic trifluoromethyl alcohols from 1-trifluoromethyl-epoxy ethers
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Andrei Kornilov、Nathalie Fischer-Durand

  DOI：10.1016/s0022-1139(96)03452-5

  日期：1996.9

  α-Thiophenyl ketones are easily available by the regioselective ring-opening of 1-trifluoromethyl-epoxy ethers with phenyl sodium thiolate. Their in situ reduction with NaBH4, followed by oxidation with NaIO4 and thermal decomposition of the resultant sulphoxides, provided allylic trifluoromethyl alcohols in high overall yield.

  通过1-三氟甲基-环氧醚与苯基硫醇钠的区域选择性开环，可轻松获得α-噻吩酮。它们用NaBH 4原位还原，然后用NaIO 4氧化并热分解生成的亚砜，提供了高总收率的烯丙基三氟甲基醇。
• Preparation of trifluoromethylated allylic alcohols from trifluoroacetaldehyde and organometallic compounds
  作者：Nobuo Ishikawa、Gyu Koh Moon、Tomoya Kitazume、Kwon Choi Sam

  DOI：10.1016/s0022-1139(00)83162-0

  日期：1984.4

  A number of allylic alcohols bearing a trifluoromethyl group at the α- or γ-position, and α-trifluoromethylated γ-enols and -ynols were prepared by the reaction of trifluoroacetaldehyde with a variety of organometallic compounds. Most of the Reformatsky- or Grignard-type reactions required promotion by ultrasonic irradiation.

  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。
• 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。
• Visible-Light-Induced Nickel-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Alcohols
  作者：Feng Chen、Xiu-Hua Xu、Lingling Chu、Feng-Ling Qing

  DOI：10.1021/acs.orglett.2c03943

  日期：2022.12.23

  phthalimido trifluoroethanol with aryl bromides to furnish α-aryl-α-trifluoromethyl alcohols is reported. This reaction proceeds via a photoinduced charge transfer of an electron donor–acceptor complex between Hantzsch ester and phthalimido trifluoroethanol, followed by 1,2-hydrogen atom transfer, to generate the α-hydroxytrifluoroethyl radical for the cross-coupling of aryl bromides. No exogenous photocatalysts

  报道了邻苯二甲酰亚氨基三氟乙醇与芳基溴的光化学诱导的镍催化自由基交叉偶联以提供 α-芳基-α-三氟甲基醇。该反应通过 Hantzsch 酯和邻苯二甲酰亚胺基三氟乙醇之间的电子供体-受体复合物的光诱导电荷转移进行，然后进行 1,2-氢原子转移，生成 α-羟基三氟乙基自由基，用于芳基溴的交叉偶联。这种温和且操作简单的协议不需要外源光催化剂或化学计量金属还原剂。观察到广泛的底物相容性和优异的官能团耐受性。
• 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。