(3R)-2-甲基庚烷-3-醇 | 26549-26-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3R)-2-甲基庚烷-3-醇
• 英文名称: (R)-2-methylheptan-3-ol
• 英文别名: (3R)-2-methylheptan-3-ol
• CAS: 26549-26-8
• 化学式: C₈H₁₈O
• 分子量: 130.23
• InChiKey: QGVFLDUEHSIZIG-MRVPVSSYSA-N

物化性质

• 沸点：
  120 °C(Press: 80 Torr)
• 密度：
  0.819±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3R)-2-甲基庚烷-3-醇 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 以99%的产率得到(2S,1'R)-1'-isopropylpentyl-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

  摘要：

  Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone I were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S, 5S)-2,6-dimethyl3, 5-heptanediol 12a. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.013
• 作为产物：
  描述：

  3-methyl-1-phenylsulfonyl-2-butanone 在 palladium on activated charcoal phosphate buffer 、 葡萄糖 、 Pichia minuta IAM 12215 strain 、 氢气 、 lithium 、 乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， -78.0~30.0 ℃ 、101.33 kPa 条件下， 反应 45.5h， 生成 (3R)-2-甲基庚烷-3-醇
  参考文献：
  名称：

  Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

  摘要：

  Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone I were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S, 5S)-2,6-dimethyl3, 5-heptanediol 12a. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.013

文献信息

• Asymmetric synthesis based on chiral diamines having pyrrolidine ring
  作者：Teruaki Mukaiyama

  DOI：10.1016/s0040-4020(01)93286-7

  日期：——

  Various highly stereoselective asymmetric reactions based on chiral diamines having pyrrolidine ring are described. Some of these reactions have been successfully applied to the syntheses of natural products.

  描述了基于具有吡咯烷环的手性二胺的各种高度立体选择性的不对称反应。这些反应中的一些已经成功地应用于天然产物的合成。
• Opening of Tartrate Acetals Using Dialkylboron Bromide:  Evidence for Stereoselectivity Downstream from Ring Fission
  作者：Yvan Guindon、William W. Ogilvie、Josée Bordeleau、Wei Li Cui、Kathy Durkin、Vida Gorys、Hélène Juteau、René Lemieux、Dennis Liotta、Bruno Simoneau、Christiane Yoakim

  DOI：10.1021/ja012530g

  日期：2003.1.1

  Johnson-type acetals derived from dimethyl tartrate give, after opening with Me(2)BBr and cuprate displacement, secondary alcohols with high diastereoselectivity (>30:1). The mechanism proposed for the induction of diastereoselectivity is downstream from the ring fission. It implies a direct participation of the Lewis acid as a source of nucleophile and the stereospecific transformation of the resulting

  由酒石酸二甲酯衍生的约翰逊型缩醛，在用 Me(2)BBr 和铜酸盐置换后，产生具有高非对映选择性 (>30:1) 的仲醇。用于诱导非对映选择性的机制是环裂变的下游。这意味着路易斯酸作为亲核试剂来源的直接参与以及所得溴缩醛的立体有择转化通过反转和温度依赖性过程。通过所需醛与酒石酸二甲酯反应制备缩醛。助剂的去除是通过 SmI(2) 还原或通过使用甲醇盐的加成消除协议来完成的。
• Investigation of the Deprotonative Generation and Borylation of Diamine-Ligated α-Lithiated Carbamates and Benzoates by in Situ IR spectroscopy
  作者：Rory C. Mykura、Simon Veth、Ana Varela、Lydia Dewis、Joshua J. Farndon、Eddie L. Myers、Varinder K. Aggarwal

  DOI：10.1021/jacs.8b06871

  日期：2018.11.7

  Diamine-mediated α-deprotonation of O-alkyl carbamates or benzoates with alkyllithium reagents, trapping of the carbanion with organoboron compounds, and 1,2-metalate rearrangement of the resulting boronate complex are the primary steps by which organoboron compounds can be stereoselectively homologated. Although the final step can be easily monitored by 11B NMR spectroscopy, the first two steps, which

  二胺介导的 O-烷基氨基甲酸酯或苯甲酸酯与烷基锂试剂的 α-去质子化、用有机硼化合物捕获碳负离子以及所得硼酸盐络合物的 1,2-金属酸盐重排是有机硼化合物立体选择性同系化的主要步骤。虽然最后一步可以很容易地通过 11B 核磁共振光谱进行监测，但由于需要专门的分析技术，通常在低温下进行的前两个步骤不太为人所知。通过原位红外光谱对这些步骤的研究为优化有机硼化合物的同系化反应提供了宝贵的数据。虽然苯甲酸酯在非配位溶剂中的去质子化比在醚类溶剂中快，氨基甲酸酯的去质子化表现出相反的趋势，这种差异源于氨基甲酸酯与二胺连接的烷基锂试剂形成无活性寄生复合物的倾向。由于在硼-锂交换之前需要将硼上的二醇配体的氧原子与锂离子初始络合，因此在甲苯中大体积二胺配位的锂化物质的硼化反应非常缓慢。然而，醚溶剂或极少量的 THF 通过初始置换与锂离子配位的大体积二胺促进预络合。
• Stereoselective opening of acetals derived from dimethyl tartrate
  作者：Y. Guindon、B. Simoneaua、C. Yoakima、V. Gorysa、R. Lemieuxa、W. Ogilvie

  DOI：10.1016/0040-4039(91)80056-c

  日期：1991.9

  Acetals of dimethyl tartrate can be used to prepare optically active secondary alcohols from the corresponding aldehydes. The key step involves treatment of the acetals with dialkylboron bromides and higher order cuprates. The process involves an unusual mechanism and produces diastereoselectivities up to 82:1.