(S)-3-[hydroxy(4-trifluoromethylphenyl)methyl]but-3-en-2-one | 1246299-52-4

• 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)-3-[hydroxy(4-trifluoromethylphenyl)methyl]but-3-en-2-one
• 英文别名: 3-[(S)-hydroxy-[4-(trifluoromethyl)phenyl]methyl]but-3-en-2-one
• CAS: 1246299-52-4
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: HJELZDZKWDSNEE-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 丁烯酮 在 硼烷四氢呋喃络合物 、 (+)-(2S,5S)-2,5-diphenyltetrahydrothiophene 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以32%的产率得到
  参考文献：
  名称：

  Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis–Hillman reactions

  摘要：

  Enantiomerically pure (2S,6S)-2,6-diphenyltetrahydro-2H-thiopyran, (2S)-2-phenyltetrahydro thiophene, and (2S)-2-phenyltetrahydro-2H-thiopyran were prepared in 70-72% yields and with 86-99% ee via cyclization of the corresponding dimesylate in an S(N)2 cyclization reaction using sodium sulfide nonahydrate. The results on the application of various chiral sulfides in asymmetric Baylis-Hillman reactions are also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.021

文献信息

• Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry
  作者：Mickael Pouliquen、Jérôme Blanchet、Michaël De Paolis、B. Rema Devi、Jacques Rouden、Marie-Claire Lasne、Jacques Maddaluno

  DOI：10.1016/j.tetasy.2010.04.038

  日期：2010.6

  Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee. (C) 2010 Elsevier Ltd. All rights reserved.