(2R)-toluene-4-sulfonic acid 2-hydroxynonyl ester | 208589-17-7

• 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: (2R)-toluene-4-sulfonic acid 2-hydroxynonyl ester
• 英文别名: [(2R)-2-hydroxynonyl] 4-methylbenzenesulfonate
• CAS: 208589-17-7
• 化学式: C₁₆H₂₆O₄S
• 分子量: 314.446
• InChiKey: PGAKKHFEGPXQSH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-toluene-4-sulfonic acid 2-hydroxynonyl ester 在 正丁基锂 、 氨 、 lithium 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 12.5h， 生成 (R,E)-7-methoxytetradec-4-en-1-ol
  参考文献：
  名称：

  Total synthesis of malyngamide X and its 7′S-epi isomer

  摘要：

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.035
• 作为产物：
  描述：

  (R)-1-O-Benzylnonane-1,2-diol 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 二正丁基氧化锡 、 三乙胺 作用下， 以 乙腈 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 (2R)-toluene-4-sulfonic acid 2-hydroxynonyl ester
  参考文献：
  名称：

  两种天然酚式高苄基酯的合成及绝对构型

  摘要：

  以对映纯的形式合成了两种最近鉴定出的天然酚类高苄基酯，分别从芦苇（兰花）和紫茎泽兰TURCZ（菊苣科的一种多年生草本植物）中分离出来。通过比较合成样品和天然样品的旋光度，可以可靠地指定天然产品的绝对构型。该合成还能够建立密切相关的天然高苄基醇的绝对构型，并首次提供了另外两种天然高纯苄基酯的完整的物理和光谱数据。

  DOI：

  10.1002/cjoc.201500315

文献信息

• Preparation of Optically Active 1,2-Diol Monotosylates by Enzymatic Hydrolysis
  作者：Kazutsugu Matsumoto、Yasutaka Shimada、Hiroshi Sato、Shinji Minowa

  DOI：10.1055/s-2008-1032047

  日期：2008.2

  An easy preparation of optically active 1,2-diol monotosylate derivatives by enzymatic hydrolysis is disclosed. Lipase PS ( BURKHOLDERIA CEPACIA) catalyzes the hydrolysis of racemic 2-acetoxyhexyl tosylate with excellent enantioselectivity to afford the corresponding optically active compounds. In this reaction, a unique temperature effect is observed. After optimizing the reaction conditions, this

  公开了通过酶促水解容易制备光学活性的1,2-二醇单甲苯磺酸酯衍生物。脂肪酶 PS (BURKHOLDERIA CEPACIA) 以优异的对映选择性催化外消旋甲苯磺酸 2-乙酰氧基己酯的水解，以提供相应的旋光化合物。在该反应中，观察到独特的温度效应。优化反应条件后，该方法可广泛应用于各种高ee光学活性化合物的两种对映体的实际制备。
• Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors
  作者：Choung U. Kim、Willard Lew、Matthew A. Williams、Huiwei Wu、Lijun Zhang、Xiaowu Chen、Paul A. Escarpe、Dirk B. Mendel、W. Graeme Laver、Raymond C. Stevens

  DOI：10.1021/jm980162u

  日期：1998.7.1

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.
• Total synthesis of malyngamide X and its 7′S-epi isomer
  作者：Suchada Suntornchashwej、Khanit Suwanborirux、Minoru Isobe

  DOI：10.1016/j.tet.2007.01.035

  日期：2007.4

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and Absolute Configuration of Two Natural Phenolic Homobenzyl Esters
  作者：Murong Xu、Shijun Zhu、Zejun Xu、Yikang Wu、Po Gao

  DOI：10.1002/cjoc.201500315

  日期：2015.7

  natural phenolic homobenzyl esters, isolated from Phragmipedium calurum (an orchid) and Eupatorium fortunei TURCZ (a perennial herb in the Asteraceae family), respectively, were synthesized in enantiopure forms. By comparison of the optical rotations for the synthetic and the natural samples, the absolute configurations for the natural products were reliably assigned. The synthesis also enables establishment

  以对映纯的形式合成了两种最近鉴定出的天然酚类高苄基酯，分别从芦苇（兰花）和紫茎泽兰TURCZ（菊苣科的一种多年生草本植物）中分离出来。通过比较合成样品和天然样品的旋光度，可以可靠地指定天然产品的绝对构型。该合成还能够建立密切相关的天然高苄基醇的绝对构型，并首次提供了另外两种天然高纯苄基酯的完整的物理和光谱数据。