(S)-(+)-2-methyl-1-heptanol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(+)-2-methyl-1-heptanol
• 英文别名: (s)-2-Methyl-heptan-1-ol；(2S)-2-methylheptan-1-ol
• 化学式: C₈H₁₈O
• 分子量: 130.23
• InChiKey: QZESEQBMSFFHRY-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  5
• 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：

  (S)-(+)-2-methyl-1-heptanol 在 hexaammonium heptamolybdate tetrahydrate 、 偶氮二甲酸二异丙酯 、 双氧水 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 (S)-5-(2-methylheptylsulfonyl)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  从头制备手性非蛋白氨基酸的新型抗疟疾脂肽的绝对构型和全合成

  摘要：

  绝对构型（通过降解和Marfey的衍生化研究）和从链霉菌属分离的新型抗疟疾脂肽的总合成。公开了（IC 50＝0.8μM，恶性疟原虫3D7）。为此，已经开发了多种非立体氨基酸途径（通过催化曼尼奇，Sharpless方法）和对映体反式脂肪酸（通过埃文斯烷基化，科辛斯基-朱莉亚烯化）的立体控制途径。

  DOI：

  10.1021/ol300293a
• 作为产物：
  描述：

  2-甲基-1-庚醇 在 Candida rogusa lipase 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 13.0h， 生成 (S)-(+)-2-methyl-1-heptanol
  参考文献：
  名称：

  Synthesis, absolute stereochemistry and molecular design of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201

  摘要：

  The absolute stereochemistry of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201 has been established by achieving the total synthesis of the product. A series of analogues have also been synthesized by changing the side chain and their bioactivity assessed against different microbial strains. Among them, le (R = C8H17) was found to be the most potent with MIC of 8 mug/mL against Mycobacterium tuberculosis, 12 mug/mL against Escherichia coli and 16 mug/mL against Bacillus subtilis 6 mug/ml against Proteus vulgaris. This was followed by 1b (R = C5H11) with MIC of 10-20 mug/mL range and Id (R = C7H15) with MIC of 14-24 g/mL, whereas la (R = C4H9) and If (R = C18H35) were found to be completely inactive. Besides, le (R = C6H13) showed certain extent of antibacterial activity in the range of 24-50 mug/mL. Mycobacterium tuberculosis was very sensitive to le (R = C8H17) with MIC of 8 mug/mL. Antifungal activity of analogues III (R = C7H15) and le, (R = C8H17) against Fusarium oxysporum and Rhizoctonia solani were found promising with MFCs in the 15-18 mug/mL range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.025

文献信息

• [EN] HSL INHIBITORS USEFUL IN THE TREATMENT OF DIABETES<br/>[FR] INHIBITEURS DE HSL UTILES DANS LE TRAITEMENT DU DIABÈTE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011029808A1

  公开（公告）日：2011-03-17

  Compounds of formula (I), as well as pharmaceutically acceptable salts thereof can be used in the form of pharmaceutical compositions, wherein A1, A2, R1,R2 R3,R4 R5 and R6 have the significance given in claim 1. Objects of the present invention are the compounds of formula (I) and their aforementioned salts and esters and their use as therapeutically active substances, a process for the manufacture of the said compounds, intermediates, pharmaceutical compositions, medicaments containing the said compounds, their pharmaceutically acceptable salts or esters, the use of the said compounds, salts or esters for the treatment or prophylaxis of illnesses, especially in the treatment or prophylaxis of diabetes, metabolic syndrome, dyslipidemia, atherosclerosis or obesity and the use of the said compounds, salts or esters for the production of medicaments for the treatment or prophylaxis of diabetes, metabolic syndrome, dyslipidemia, atherosclerosis or obesity.

  化合物的化学式（I），以及其药学上可接受的盐可以用作药物组合物的形式，其中A1，A2，R1，R2，R3，R4，R5和R6具有权利要求1中给定的含义。本发明的目的是化学式（I）的化合物及其上述的盐和酯，以及它们作为治疗活性物质的用途，制造所述化合物的方法，中间体，含有所述化合物的药物组合物，含有所述化合物、其药学上可接受的盐或酯的药物，所述化合物、盐或酯的用途用于治疗或预防疾病，特别是用于治疗或预防糖尿病、代谢综合征、血脂异常、动脉粥样硬化或肥胖症，以及所述化合物、盐或酯的用途用于生产用于治疗或预防糖尿病、代谢综合征、血脂异常、动脉粥样硬化或肥胖症的药物。
• Remote Chiral Communication in Coadsorber-Induced Enantioselective 2D Supramolecular Assembly at a Liquid/Solid Interface
  作者：Ting Chen、Shu-Ying Li、Dong Wang、Man Yao、Li-Jun Wan

  DOI：10.1002/anie.201410927

  日期：2015.3.27

  Remote chiral communication in 2D supramolecular assembly at a liquid/solid interface was investigated at the molecular level. The stereochemical information in a chiral coadsorber was transmitted over a flexible spacer with a length of up to five methylene groups to a 2D supramolecular assembly of achiral building blocks with the cooperation of specific hydrogen bonding between the chiral coadsorber

  在分子水平上研究了液/固界面上二维超分子组装中的远程手性通讯。手性共吸附剂中的立体化学信息通过最多具有五个亚甲基的长度的柔性间隔基，通过手性共吸附剂与非手性结构单元之间的特定氢键结合以及封闭效应，传递到非手性结构单元的二维超分子组装中在2D结晶过程中。当相对于立体控制部分改变立体发生中心的位置时，发现了奇偶效应。靠近立体控制部分的立体中心更可靠地将立体化学信息传递给2D超分子组装体。
• Asymmetric alkylation of N-acylsultams: A general route to enantiomerically pure, crystalline C(α,α)-disubstituted carboxylic acid derivatives
  作者：Wolfgang Oppolzer、Robert Moretti、Silvia Thomi

  DOI：10.1016/s0040-4039(01)93810-9

  日期：1989.1

  Successive treatment of acylsultams with nBuLi or NHMDS and primary alkyl halides, followed by crystallization, gave pure C(α)-alkylation products and, via their non-destructive cleavage, enantiomerically pure alcohols or carboxylic acids .

  用n BuLi或NHMDS和伯烷基卤连续处理酰基磺酰胺，然后结晶，得到纯C（α）-烷基化产物，并通过它们的非破坏性裂解，得到对映体纯的醇或羧酸。
• Application of Trimethylgermanyl-Substituted Bisphosphine Ligands with Enhanced Dispersion Interactions to Copper-Catalyzed Hydroboration of Disubstituted Alkenes
  作者：Yumeng Xi、Bo Su、Xiaotian Qi、Shayun Pedram、Peng Liu、John F. Hartwig

  DOI：10.1021/jacs.0c08746

  日期：2020.10.21

  report the incorporation of large substituents based on heavy main group elements that are atypical in ligand architectures to enhance dispersion interactions and, thereby, enhance enantioselectivity. Specifically, we prepared the chiral biaryl bisphosphine ligand (TMG-SYNPHOS) containing 3,5-bis(trimethylgermanyl)phenyl groups on phosphorus and applied this ligand to the challenging problem of enantioselective

  我们报告了基于重主族元素的大取代基的掺入，这些元素在配体结构中是非典型的，以增强分散相互作用，从而增强对映选择性。具体来说，我们制备了在磷上含有 3,5-双（三甲基锗基）苯基的手性联芳基双膦配体 (TMG-SYNPHOS)，并将该配体应用于 1,1-二取代烯烃的对映选择性加氢官能化反应的挑战性问题。事实上，TMG-SYNPHOS 形成了一种铜络合物，即使两个取代基都是伯烷基，也能以高水平的对映选择性催化 1,1-二取代烯烃的硼氢化。此外，带有具有锗基的配体的铜催化剂比衍生自 DTBM-SEGPHOS（一种含有 2、5-二叔丁基基团，广泛用于铜催化的氢官能化。这一观察导致鉴定了 DTMGM-SEGPHOS，一种带有 3,5-双（三甲基锗基）-4-甲氧基苯基作为磷上取代基的双膦配体，作为一种新的配体，可形成用于未活化 1 硼氢化的高活性催化剂,2-二取代烯烃，一类以前不容易经历铜催化硼氢化的底物。
• Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by<i>Acetobacter aceti</i>
  作者：Elisabetta Brenna、Flavia Cannavale、Michele Crotti、Valerio De Vitis、Francesco G. Gatti、Gaia Migliazza、Francesco Molinari、Fabio Parmeggiani、Diego Romano、Sara Santangelo

  DOI：10.1002/cctc.201601051

  日期：2016.12.19

  achiral 2‐alkyl‐1,3‐diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2‐hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available

  非手性2-烷基-1,3-二醇的立体选择性去对称化是通过醋乙酸醋杆菌MIM 2000/28氧化两个对位伯醇部分之一进行的，以提供相应的手性2-羟甲基链烷酸（最高94 ％ee）。该过程在pH，温度和压力中等的水性介质中进行，有助于扩大有机化学家可用于开发可持续生产工艺的酶促氧化反应的范围。