(S)-1-(3-trifluoromethyl-phenyl)-but-3-en-1-ol | 935559-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(3-trifluoromethyl-phenyl)-but-3-en-1-ol
• 英文别名: (S)-1-(3-Trifluoromethylphenyl)-3-buten-1-ol；(1S)-1-[3-(trifluoromethyl)phenyl]but-3-en-1-ol
• CAS: 935559-75-4
• 化学式: C₁₁H₁₁F₃O
• 分子量: 216.203
• InChiKey: ITTIGOPRDIDCRE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (S)-1-(3-trifluoromethyl-phenyl)-but-3-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 臭氧 、 N,N-二异丙基乙胺 、 甲基磺酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [(2S)-2-(3-trifluoromethyl-phenyl)-cyclopropyl]-methanol
  参考文献：
  名称：

  Competitive Cationic Pathways and the Asymmetric Synthesis of Aryl-Substituted Cyclopropanes

  摘要：

  Disubstituted cyclopropanes were synthesized in a nonracemic fashion via activation of the corresponding homoallylic alcohols in excellent yields. A series of substituted phenyl rings showed higher enantiospecificity for the cyclization as the electron-withdrawing ability of the group increased. The results offer strong support for the existence of competing cation mechanisms.

  DOI：

  10.1021/ol063026p
• 作为产物：
  描述：

  丙烯基三氯硅烷 、 3-三氟甲基苯甲醛 在 Phosphorsaeure-(3,3'-dimethyl-1,1'-binaphtyl-2,2'-diyl)-diester 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (S)-1-(3-trifluoromethyl-phenyl)-but-3-en-1-ol 、 (R)-1-(3-trifluoromethyl-phenyl)-but-3-en-1-ol
  参考文献：
  名称：

  手性磷酸催化烯丙基三氯硅烷对醛的对映选择性烯丙基化

  摘要：

  容易获得的手性磷酸1b已被用作有效的有机催化剂，用于醛与烯丙基三氯硅烷的不对称烯丙基化。在20mol％的1b的存在下，各种醛的烯丙基化顺利进行，得到相应的均丙醇，其ee高达87％，收率达97％。

  DOI：

  10.1002/cjoc.201180244

文献信息

• Asymmetric Allylation of Aldehydes Catalyzed by Simple Dual Small Organic Molecules: L-Proline and L-Prolinol
  作者：Guo-hong Chen、Ling-yan Liu、Xiao-ning Wei、Wei-xing Chang、Jing Li

  DOI：10.1246/cl.2010.1013

  日期：2010.9.5

  A novel and simple methodology for the asymmetric allylation of aldehydes was reported. Double small organic molecules such as l-proline and l-prolinol were first employed for providing a chiral environment so as to afford chiral homoallylic alcohols in high yields and moderate enantioselectivities in our protocol.

  报道了一种新颖且简单的用于醛的不对称烯基化的方法。首次使用了双小有机分子如L-脯氨酸和L-脯氨醇，提供手性环境，从而在我们的方案中获得了高产率和中等对映选择性的手性同烯醇。
• Chiral Phosphoric Acid Catalyzed Enantioselective Allylation of Aldehydes with Allyltrichlorosilane
  作者：Ke Cheng、Tiantian Fan、Jian Sun

  DOI：10.1002/cjoc.201180244

  日期：2011.8

  Easily accessible chiral phosphoric acid 1b has been applied as efficient organocatalyst for the asymmetric allylation of aldehydes with allyltrichlorosilane. In the presence of 20 mol% of 1b, the allylation of a broad range of aldehydes proceeded smoothly to give the corresponding homoallylic alcohol with up to 87% ee and 97% yield.

  容易获得的手性磷酸1b已被用作有效的有机催化剂，用于醛与烯丙基三氯硅烷的不对称烯丙基化。在20mol％的1b的存在下，各种醛的烯丙基化顺利进行，得到相应的均丙醇，其ee高达87％，收率达97％。
• Competitive Cationic Pathways and the Asymmetric Synthesis of Aryl-Substituted Cyclopropanes
  作者：Bruce J. Melancon、Nicholas R. Perl、Richard E. Taylor

  DOI：10.1021/ol063026p

  日期：2007.4.1

  Disubstituted cyclopropanes were synthesized in a nonracemic fashion via activation of the corresponding homoallylic alcohols in excellent yields. A series of substituted phenyl rings showed higher enantiospecificity for the cyclization as the electron-withdrawing ability of the group increased. The results offer strong support for the existence of competing cation mechanisms.