(R)-3-[hydroxy(phenyl)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: (R)-3-[hydroxy(phenyl)methyl]but-3-en-2-one
• 英文别名: (R)-3-[hydroxyphenylmethyl]but-3-en-2-one；3-[(R)-hydroxy(phenyl)methyl]but-3-en-2-one
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: JOZQRTNMSJPYQB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 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：

  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 3.17h， 以48%的产率得到(R)-3-[hydroxy(phenyl)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

• Brucine N-oxide-catalyzed Morita–Baylis–Hillman reaction of vinyl ketones: a mechanistic implication of dual catalyst system with proline
  作者：Kyungsoo Oh、Jian-Yuan Li、Jinhyang Ryu

  DOI：10.1039/c003667f

  日期：——

  The brucine N-oxide promoted Morita–Baylis–Hillman (MBH) reaction of vinyl ketones with aldehydes has been achieved. The corresponding asymmetric version of MBH reaction was also investigated, and the electron-deficient aryl aldehydes have emerged as suitable reaction partners for vinyl ketones; where proline was employed as a co-catalyst. In this dual catalyst system, proline is believed to form iminium

  原始的N氧化物促进了Morita–Baylis–Hillman（MBH）已经实现了乙烯基酮与醛的反应。对应的不对称版本MBH还对反应进行了研究，并且出现了缺电子的芳基醛作为乙烯基酮的合适反应伙伴。在哪里脯氨酸被用作助催化剂。在这种双重催化剂系统中，脯氨酸认为N-氧化物与缺电子的芳基醛形成亚胺中间体，而N-氧化物活化乙烯基酮以通过共轭加成提供烯醇化物。结合这两种中间体后，通过控制速率确定步骤可以得到高对映选择性的MBH产物。H桥接的椅子状过渡状态。本质上，结果MBH发现产物醇类干扰中间体，烯醇化物和脯氨酸亚胺鎓中间体两者的形成，因此观察到的产物的对映选择性在进一步反应转化时减弱，可能是由于自催化作用。本研究为衍生自缺电子的芳基醛和脯氨酸。
• N-Methylprolinol Catalysed Asymmetric Baylis−Hillman Reaction
  作者：Palakodety Radha Krishna、V. Kannan、P. V. Narasimha Reddy

  DOI：10.1002/adsc.200303217

  日期：2004.5

  N-methylprolinol is used as a chiral base catalyst for the Baylis–Hillman reaction to obtain the adducts in good yields with moderate to good enantioselectivities in 1,4-dioxane:water (1 : 1, v/v) under ambient conditions.

  N-甲基脯氨醇用作Baylis-Hillman反应的手性碱催化剂，可在环境条件下在1,4-二恶烷：水（1：1，v / v）中以良好的产率获得具有中等至良好对映选择性的加合物。
• 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].