(R)-3-[hydroxy(4-chlorophenyl)methyl]but-3-en-2-one | 500167-72-6

• 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: (R)-3-[hydroxy(4-chlorophenyl)methyl]but-3-en-2-one
• 英文别名: 3-[(R)-(4-Chlorophenyl)(hydroxy)methyl]but-3-en-2-one；3-[(R)-(4-chlorophenyl)-hydroxymethyl]but-3-en-2-one
• CAS: 500167-72-6
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: JIROGNRDKVCNAQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 丁烯酮 在 1-[(1R,2R)-2-diphenylphosphanylcyclohexyl]-3-phenylthiourea 作用下， 以 氯仿 为溶剂， 反应 2.17h， 以40%的产率得到(R)-3-[hydroxy(4-chlorophenyl)methyl]but-3-en-2-one
  参考文献：
  名称：

  芳香醛与甲基乙烯基酮的对映选择性森田-贝利斯-希尔曼反应中的手性膦硫脲有机催化剂

  摘要：

  新型的手性膦硫脲已被开发为有效的有机催化剂，用于芳香醛与甲基乙烯基酮的对映选择性Morita-Baylis-Hillman反应。反应在非常温和的条件下进行，可以在短时间内以高达94％ee的良好收率获得所需的产物。

  DOI：

  10.1016/j.tetlet.2008.08.042

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％。
• Asymmetric Morita–Baylis–Hillman reactions of 2-cyclohexen-1-one catalyzed by chiral biaryl-based bis(thiourea) organocatalysts
  作者：Yuki Nakayama、Takashi Gotanda、Katsuji Ito

  DOI：10.1016/j.tetlet.2011.09.064

  日期：2011.11

  Newly-developed bis(thiourea) 1d was found to be an efficient organocatalyst for the Morita-Baylis-Hillman reaction. High enantioselectivities were obtained in the reaction of 2-cyclohexen-1-one with both aromatic aldehydes (up to 84% ee) and aliphatic aldehydes (up to 96% ee). (C) 2011 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.
• 10.24820/ark.5550190.p011.072dummy2
  作者：Aydin, A. Ebru

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

  日期：——
• 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].