(R)-2-[(S)-(2-bromophenyl)(hydroxy)methyl]cyclohexanone

• 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)-2-[(S)-(2-bromophenyl)(hydroxy)methyl]cyclohexanone
• 英文别名: 2-(hydroxy(2-bromophenyl)methyl)cyclohexanone；(R)-2-((S)-hydroxy(2-bromophenyl)methyl)cyclohexan-1-one；(2R)-2-[(S)-(2-bromophenyl)-hydroxymethyl]cyclohexan-1-one
• 化学式: C₁₃H₁₅BrO₂
• 分子量: 283.165
• InChiKey: QWIVZAMLWMTHPR-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  环己酮 、 邻溴苯甲醛 在 L-proline-based tripeptide 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (R)-2-[(S)-(2-bromophenyl)(hydroxy)methyl]cyclohexanone 、 (S)-2-[(R)-(2-bromophenyl)(hydroxy)methyl]cyclohexanone
  参考文献：
  名称：

  Short α/β-Peptides as Catalysts for Intra- and Intermolecular Aldol Reactions

  摘要：

  Short alpha/beta-peptides, containing conformationally restricted cis-beta-aminocyclopropylcarboxylic acid units as turn-inducing elements, have been found to be efficient catalysts for inter- and intramolecular aldol reactions. The tripeptide H-(L)-Pro-triangle-(L)-Pro-OH was identified to perform especially well in homogeneous and heterogeneous aqueous solutions as well as in organic solvents.

  DOI：

  10.1021/jo800168h

文献信息

• Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst
  作者：Barry Lygo、Christopher Davison、Timothy Evans、James A.R. Gilks、John Leonard、Claude-Eric Roy

  DOI：10.1016/j.tet.2011.09.101

  日期：2011.12

  The four-step synthesis of a chiral primary tertiary diamine salt, possessing a tropos dibenz[c,e]azepine ring is described. It is shown that 3.5–5 mol % of this salt is capable of promoting highly enantioselective crossed-aldol reactions between cyclohexanone and a series of aromatic aldehydes. In all cases, the aldol reactions proceed with high diastereoselectivity for the anti-aldol product. The

  描述了具有对位二苯并[ c，e ] a庚环的手性伯叔二胺盐的四步合成。结果表明，这种盐的3.5–5 mol％能够促进环己酮与一系列芳香醛之间的高度对映选择性的交叉羟醛反应。在所有情况下，羟醛缩合反应继续进行高非对映选择性的反-aldol产品。还描述了涉及其他环状酮和非环状酮的交叉醇醛缩合反应的结果。所有涉及环状酮的例子都会导致对抗羟醛产物的选择性，而发现非环状酮有利于合成-aldol产品。还讨论了手性伯叔二胺盐在醛醇缩合反应催化中的作用。
• Different bio/Lewis acid-catalyzed stereoselective aldol reactions in various mediums
  作者：Tülay Yıldız、Hasniye Yaşa、Belma Hasdemir、Ayşe S. Yusufoğlu

  DOI：10.1007/s00706-017-1967-z

  日期：2017.8

  Brønsted acids were used for asymmetric aldol reactions of aromatic, heteroaromatic, cyclic, and acyclic six ketones and eleven aldehydes. Optimum reaction conditions were determined by changing temperature and enzyme, ketone, aldehyde, solvent, cofactors types, amounts, and ratios. PPL (porcine pancreatic lipase) of animal and AL-AN (amano lipase A from Aspergillus niger) of fungal origins were the

  摘要在这项工作中，八种不同的粗制生物催化剂与六种路易斯酸和三种布朗斯台德酸一起用于芳族，杂芳族，环状和无环六种酮和十一种醛的不对称羟醛反应。最佳反应条件是通过改变温度和酶，酮，醛，溶剂，辅因子的类型，数量和比例来确定的。动物的PPL（猪胰脂肪酶）和真菌来源的AL-AN（黑曲霉的天基脂肪酶A ）是最好的，并且相互比较。CoCl 2是最好的辅因子，与没有辅因子相比，它能更好地催化酶促醛缩反应。CoCl 2以前未用于酶促醛醇缩合反应。本研究中的方法使用粗制生物催化剂（PPL或AL-AN）和CoCl乙腈-水中的2被发现是不对称醛醇缩合反应的常规有用的生物催化方法，并且具有比文献中更好的ee值。 图形概要
• Evaluation of Amino Nitriles and an Amino Imidate as Organo­catalysts in Aldol Reactions
  作者：Nikolaos Vagkidis、Alexander J. Brown、Paul A. Clarke

  DOI：10.1055/s-0039-1690150

  日期：2019.11

  and a tert-butyl­ l-proline imidate as organocatalysts for the aldol reaction have been evaluated. l-Valine nitrile was found to be a syn-selective catalyst, while l-proline nitrile was found to be anti-selective, and gave products in modest to good enantioselectivities. tert-Butyl l-proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and

  抽象的 的效率升-缬氨酸和升-脯氨酸腈和叔丁基升-脯氨酸亚氨酸酯作为醛醇缩合反应的有机催化剂进行了评价。升缬氨酸腈被发现是一个SYN -选择性催化剂，而升脯氨酸腈被认为是抗体选择性，并给了产品在适度良好的对映选择性。叔丁基升-proline亚胺酯被发现是在起始试剂产品的转化率来表示一个非常有效的催化剂，并得到良好的抗-选择性。叔丁基的对映选择性升-脯氨酸亚氨酸酯被认为是卓越的，与形成在高达94％的对映体过量的产品。 的效率升-缬氨酸和升-脯氨酸腈和叔丁基升-脯氨酸亚氨酸酯作为醛醇缩合反应的有机催化剂进行了评价。升缬氨酸腈被发现是一个SYN -选择性催化剂，而升脯氨酸腈被认为是抗体选择性，并给了产品在适度良好的对映选择性。叔丁基升-proline亚胺酯被发现是在起始试剂产品的转化率来表示一个非常有效的催化剂，并得到良好的抗-选择性。叔丁基的对映选择性升-脯氨酸亚氨酸酯被认为是卓越的，与形成在高达94％的对映体过量的产品。
• Protonated (S)-prolinamide derivatives—water compatible organocatalysts for direct asymmetric aldol reaction
  作者：Swapandeep Singh Chimni、Sarbjit Singh、Dinesh Mahajan

  DOI：10.1016/j.tetasy.2008.09.020

  日期：2008.10

  as water compatible highly efficient organocatalysts for a direct enantioselective aldol reaction. A simple protonated (S)-prolinamide organocatalyst prepared from l-proline and 3-nitroaniline catalyzes the aldol reaction of unmodified ketones and a variety of aromatic aldehydes yielding aldol product in high yield with enantioselectivities of up to 98% and diastereoselectivity of up to >99:1.

  质子化的手性（S）-脯氨酰胺衍生物已被开发为与水相容的高效有机催化剂，用于直接对映选择性的醛醇缩合反应。由1-脯氨酸和3-硝基苯胺制备的简单质子化的（S）-脯氨酰胺有机催化剂可催化未修饰的酮与多种芳族醛的醛醇缩合反应，以高收率生成醛醇缩合产物，对映选择性高达98％，非对映选择性高达99：1。
• A new type of amino amide organocatalyzed enantioselective crossed aldol reaction of ketones with aromatic aldehydes
  作者：Isiaka A. Owolabi、U.V. Subba Reddy、Madhu Chennapuram、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1016/j.tet.2018.07.016

  日期：2018.9

  A new type of amino amide organocatalysts was designed and synthesized from commercially available amino acids in easy steps. Their catalytic activities were examined in enantioselective crossed aldol reaction of various acyclic and cyclic ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good to excellent chemical yields, diastereoselectivities and enantioselectivities

  设计了一种新型的氨基酰胺有机催化剂，并通过容易的步骤由市售氨基酸合成。在各种无环和环状酮与芳族醛的对映选择性交叉羟醛反应中检查了它们的催化活性，从而提供了相应的手性抗羟醛加合物，具有良好的化学收率，非对映选择性和对映选择性（高达99％，高达syn：anti  = 1:99，最高可达97％ee）。