(S)-3-[hydroxy(4-cyanophenyl)methyl]but-3-en-2-one

• 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-cyanophenyl)methyl]but-3-en-2-one
• 英文别名: 3-[hydroxy(4-cyanophenyl)methyl]but-3-en-2-one；4-[(1S)-1-hydroxy-2-methylidene-3-oxobutyl]benzonitrile
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: ULCIQDBJRNEOKO-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁烯酮 、 4-氰基苯甲醛 在 (R)-N-甲基-2-吡咯烷-1-甲基-吡咯烷 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 (S)-3-[hydroxy(4-cyanophenyl)methyl]but-3-en-2-one 、 (R)-3-[hydroxy(4-cyanophenyl)methyl]but-3-en-2-one
  参考文献：
  名称：

  手性二胺介导的不对称Baylis-Hillman反应

  摘要：

  容易从脯氨酸制备的手性二胺是醛和甲基乙烯基酮的Baylis-Hillman反应的有效，不对称有机催化剂，提供的对映选择性高达75％。

  DOI：

  10.1002/adsc.200404069

文献信息

• The Chiral Diamine Mediated Asymmetric Baylis–Hillman Reaction
  作者：Yujiro Hayashi、Tomohiro Tamura、Mitsuru Shoji

  DOI：10.1002/adsc.200404069

  日期：2004.8

  A chiral diamine, easily prepared from proline, is an effective, asymmetric organic catalyst for the Baylis–Hillman reaction of aldehydes and methyl vinyl ketone, affording adducts with enantioselectivities up to 75%.

  容易从脯氨酸制备的手性二胺是醛和甲基乙烯基酮的Baylis-Hillman反应的有效，不对称有机催化剂，提供的对映选择性高达75％。
• 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.
• Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis–Hillman reactions
  作者：Mariappan Periasamy、Ramani Gurubrahamam、Gopal P. Muthukumaragopal

  DOI：10.1016/j.tetasy.2013.03.021

  日期：2013.5

  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.
• Chiral thiourea derivatives as organocatalyts in the enantioselective Morita-Baylis-Hillman reactions
  作者：A. Ebru Aydin

  DOI：10.24820/ark.5550190.p011.072

  日期：——

  Novel chiral bifunctional thiourea derivatives have been synthesised and successfully applied to the intermolecular Morita-Baylis-Hillman (MBH) reaction of an aromatic aldehyde with methyl vinyl ketone (MVK) and to the intramolecular MBH reaction of omega-formyl-enone. The corresponding products were obtained with high enantioselectivities (up to 98 % ee). The thiourea organocatalyst derived from a B-amino alcohol gave high enantioselectivities (92 % ee) in the intermolecular MBH reaction, whereas the same chiral ligand afforded the corresponding product in high yield (85 %) with moderate enantioselectivity (75 % ee) in the intramolecular MBH reaction. The use of a thiophene ring-containing thiourea derivative gave high enantioselectivities in the intermolecular and intramolecular MBH reactions (85 % and 95 % ee, respectively).[GRAPHICS].
• 10.24820/ark.5550190.p011.072dummy2
  作者：Aydin, A. Ebru

  DOI：10.24820/ark.5550190.p011.072dummy2

  日期：——