(4S)-4-hydroxy-4-(1'-naphthyl)-butan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-4-hydroxy-4-(1'-naphthyl)-butan-2-one
• 英文别名: (4S)-4-hydroxy-4-naphthalen-1-ylbutan-2-one
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: ZRQWPFKGJLGSPI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  1-萘甲醛 、 丙酮 在 (1R,2R)-2-(dipropylamino)cyclohexanaminium trifluoromethanesulfonate 、 间硝基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(4S)-4-hydroxy-4-(1'-naphthyl)-butan-2-one
  参考文献：
  名称：

  用于直链脂肪酮不对称直接羟醛反应的简单伯-叔二胺-布朗斯台德酸催化剂

  摘要：

  与已充分探索的带有仲胺的烯胺催化相比，开发高效的基于烯胺的伯胺催化剂直到最近仍然是一个难以捉摸的目标。我们在本文中提出了一种简单的手性伯-叔二胺 1d 与 TfOH 结合用作有效的基于烯胺的伯胺催化剂。1d-TfOH催化体系可以有效催化不对称直接醛醇反应，底物范围广，在环境温度下具有高区域选择性和非对映选择性以及对映选择性。值得注意的是，这些反应适应了合成上重要但具有挑战性的底物，例如线性脂肪族酮，具有高区域选择性和前所未有的顺式非对映选择性。

  DOI：

  10.1021/ja069372j

文献信息

• Direct Asymmetric Aldol Reaction Catalyzed by C2-Symmetrical Chiral Primary Amine Organocatalysts
  作者：Gong-Jian Zhu、Chao-Shan Da、Ya-Ning Jia、Xiao Ma、Lei Yi

  DOI：10.2174/157017810790533904

  日期：2010.1.1

  C-2-symmetrical chiral primary amines were synthesized from chiral BINOL and diamines. Then their catalytic activities in the asymmetric aldol reactions were evaluated, and the result indicated that 1c was the optimal organocatalyst. The reaction of a variety of aromatic aldehydes with aliphatic ketones, catalyzed by 20 mol % 1c in the addition of benzoic acid in carbon tetrachloride, afforded the aldol products

  从手性 BINOL 和二胺合成了三种新型 C-2 对称手性伯胺。然后评估了它们在不对称醛醇反应中的催化活性，结果表明1c是最佳的有机催化剂。在四氯化碳中加入苯甲酸，在 20 mol % 1c 的催化下，多种芳香醛与脂肪族酮反应得到高产率（高达 92%）和良好的对映选择性（高达 71%）的醛醇产物.
• Efficient asymmetric catalysis of chiral organoaluminum complex for enantioselective ene reactions of aldehydes
  作者：Takashi Ooi、Kohsuke Ohmatsu、Daisuke Uraguchi、Keiji Maruoka

  DOI：10.1016/j.tetlet.2004.04.052

  日期：2004.5

  Chiral organoaluminum complex 1 efficiently catalyzed the asymmetric hetero-ene reaction of commercially available 2-methoxypropene (2) with aldehydes under mild conditions to give the corresponding β-hydroxymethyl ketones 3 in good to excellent chemical yields with high enantiomeric excesses. The asymmetric catalysis of 1 was further applied to the carbonyl addition of methallylsilanes, where exclusive

  手性有机铝络合物1在温和的条件下有效催化了市售的2-甲氧基丙烯（2）与醛的不对称杂烯反应，从而以高至优异的化学收率和较高的对映体过量得到相应的β-羟甲基酮3。将1的不对称催化进一步应用于甲基烯丙基硅烷的羰基加成，其中实现了旋光性烯丙基硅烷5的排他性形成。
• Tandem Catalysis by Lipase in a Vinyl Acetate-Mediated Cross-Aldol Reaction
  作者：Manjeet Kumar、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1002/adsc.201000980

  日期：2011.5

  The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate‐mediated aldol reaction. The reaction was facilitated through the lipase‐catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal

  脂肪酶Novozym435（0.6％w / w）与乙酸乙烯酯/异丙烯基乙酸酯介导的醛醇缩合反应中的有机催化剂一起使用。该反应通过脂肪酶催化的乙醛/丙酮原位生成而得以促进。本方法的重要特征包括温和且容易的反应条件，脂肪酶的可再生性，相对高的收率和最小的副产物形成。
• Convenient Preparation of Chiral Dipyrrolylmethanes Containing a Chiral Moiety
  作者：Pier Giorgio Cozzi、Sandro Gambarotta、Magda Monari、Luca Zoli

  DOI：10.1135/cccc20071046

  日期：——

  A variety of chiral bis-pyrroles have been made readily accessible via acid-catalyzed condensation of chiral ketones with pyrrole. Three representative chiral ketones 2-4 taken from the chiral pool were transformed into the corresponding bis-pyrrole derivatives in a straightforward acid-catalyzed condensation. Chiral β-hydroxy ketone derivatives, prepared through proline-catalyzed aldol condensation of acetone and an aldehyde, are readily transformed into the corresponding dipyrrolylmethane by the acid-catalyzed condensation carried out in the same conditions. The crystal structure of the chiral dipyrrolylmethane 2 derived from the (-)-menthone was determined.

  一系列手性双吡咯已通过手性酮与吡咯的酸催化缩合反应方便地制备。从手性池中选取的三种代表性手性酮2-4经过简单的酸催化缩合反应转化为相应的双吡咯衍生物。通过脯氨酸催化的丙酮和醛的醛缩反应制备的手性β-羟基酮衍生物，可以方便地在相同条件下通过酸催化缩合反应转化为相应的二吡咯甲烷。从(-)-薄荷醇衍生的手性二吡咯甲烷2的晶体结构已确定。
• Unexpected Beneficial Effect of ortho-Substituents on the (S)-Proline-Catalyzed Asymmetric Aldol Reaction of Acetone with Aromatic Aldehydes
  作者：Benjamin List、Alberto Martínez、Manuel van Gemmeren

  DOI：10.1055/s-0033-1340920

  日期：——

  An intriguing effect of electronegative 2,6-substituents on the stereochemical outcome of (S) -proline-catalyzed aldol reactions between benzaldehyde derivatives and acetone is reported. Remarkably high enantioselectivities can be achieved with such substrates.

  据报道，带负电的 2,6-取代基对 (S)-脯氨酸催化的苯甲醛衍生物和丙酮之间的羟醛反应的立体化学结果产生了有趣的影响。使用此类底物可以实现非常高的对映选择性。