3-octyl methanesulfonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-octyl methanesulfonate
• 英文别名: 3-octyl mesylate；Octan-3-yl methanesulfonate
• 化学式: C₉H₂₀O₃S
• 分子量: 208.322
• InChiKey: JYQABIRAYMMNOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-octyl methanesulfonate 在 potassium fluoride 、 2-{双[3,5-双(三氟甲基)苯基]膦基}-3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯 、 copper(l) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 3-octylacetophenone
  参考文献：
  名称：

  通过亲核性烷基甲磺酸酯的亲核转化制备对映体富集的烷基氨基甲酸酯，用于立体特异性交叉偶联反应

  摘要：

  我们报告了通过对映体富集的烷基甲磺酸盐和碳原子化炔基阴离子等价物的立体转化S N 2反应制备对映体富集的仲烷基氨基甲酸酯。使用该方法，可以将对映体富集的仲醇转化为高度对映体富集的烷基碳黄烷烃，其可用于立体有择的交叉偶联反应中。

  DOI：

  10.1021/acs.organomet.9b00467
• 作为产物：
  描述：

  3-辛醇 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-octyl methanesulfonate
  参考文献：
  名称：

  通过亲核性烷基甲磺酸酯的亲核转化制备对映体富集的烷基氨基甲酸酯，用于立体特异性交叉偶联反应

  摘要：

  我们报告了通过对映体富集的烷基甲磺酸盐和碳原子化炔基阴离子等价物的立体转化S N 2反应制备对映体富集的仲烷基氨基甲酸酯。使用该方法，可以将对映体富集的仲醇转化为高度对映体富集的烷基碳黄烷烃，其可用于立体有择的交叉偶联反应中。

  DOI：

  10.1021/acs.organomet.9b00467

文献信息

• General, Robust, and Stereocomplementary Preparation of β-Ketoester Enol Tosylates as Cross-Coupling Partners Utilizing TsCl−<i>N</i>-Methylimidazole Agents
  作者：Hidefumi Nakatsuji、Kanako Ueno、Tomonori Misaki、Yoo Tanabe

  DOI：10.1021/ol800480d

  日期：2008.6.5

  (Z)-stereocomplementary enol tosylation of beta-ketoesters using TsCl- N-methylimidazole (NMI)-Et3N or LiOH. TsCl coupled with NMI formed a highly reactive N-sulfonylammonium intermediate. Stereocongested secondary alcohols were smoothly sulfonylated using Ts(Ms)Cl-NMI-Et3N. beta-Ketoesters underwent (E)-selective tosylation using TsCl-NMI-Et3N and (Z)-selective tosylation using TsCl-NMI-LiOH (total

  我们已经开发了使用TsCl-N-甲基咪唑（NMI）-Et3N或LiOH进行β-酮酸酯的（E）-或（Z）-立体互补烯醇甲苯磺酸酯化的通用，可靠且经济高效的方法。TsCl与NMI偶联形成高反应性的N-磺酰胺基中间体。使用Ts（Ms）Cl-NMI-Et3N将立体拥挤的仲醇顺利磺酰化。β-酮酸酯使用TsCl-NMI-Et3N进行（E）选择性甲苯磺酰化，使用TsCl-NMI-LiOH进行（Z）选择性甲苯磺酰化（共23个实例；收率60％-99％）。使用烯醇甲苯磺酸盐的立体定向Negishi和Sonogashira偶联成功进行，得到了三取代的α，β-不饱和酯。
• Stereo‐ and Regiochemical Effect of <i>N,N</i>‐Dialkylamide Extractants on the Speciation of Pu Complexes
  作者：David Lemire、Thomas Dumas、Cécile Marie、Fabrice Giusti、Guilhem Arrachart、Sandrine Dourdain、Stephane Pellet‐Rostaing

  DOI：10.1002/ejic.202300461

  日期：2023.11.14

  The relationship between extractant stereochemistry and their extraction performance has only poorly been established. In order to address a part of this concern, we investigated the Pu(IV) liquid‐liquid extraction (LLE) by using the N,N‐di‐(2‐ethylhexyl)butyramide (DEHBA), as well as those of its position isomers. DEHBA (ββ‐isomer) and N‐(2‐ethylhexyl)‐N‐(oct‐3‐yl)butyramide (EHOBA or αβ‐isomer) were synthesized as a mixture of stereoisomer or stereoenriched (R,S)‐ and (S,S)‐diastereoisomers, and were all assessed for Pu^IV LLE. The results showed that both the position and the stereoisomerism of the aliphatic substituents affect Pu^IV complexation and extraction. We found that Pu extraction is lowered by factor 2 to 4 when the ethyl branching group is closer to the complexing site. UV‐vis spectroscopy showed that this extraction decrease was affected by steric hindrance inducing a deprivation of Pu inner sphere complex. Effect of stereoisomerism is highlighted for branching closer to the complexing site (α‐position). Enantiopure DEHBA stereoisomers provided similar Pu extraction, whereas a slight decrease could be noticed for the more cluttered stereoenriched (αβ)‐isomers, which was also concomitant with a smaller population of inner sphere complex. In contrast, the stereoisomers mixture led to a strong decrease of Pu extraction because of an antagonistic association in the mixed complexes.

  摘要 目前，萃取剂立体化学与萃取性能之间的关系尚不十分明确。为了解决这一问题，我们使用N,N-二（2-乙基己基）丁酰胺（DEHBA）及其位置异构体研究了钚（IV）的液-液萃取（LLE）。DEHBA（ββ-异构体）和N-(2-乙基己基)-N-(辛-3-基)丁酰胺（EHOBA或αβ-异构体）被合成为立体异构体或立体富集的(R,S)-和(S,S)-非对映异构体的混合物，并对它们进行了PuIV LLE评估。结果表明，脂肪族取代基的位置和立体异构体都会影响 PuIV 的络合和萃取。我们发现，当乙基支化基团更靠近络合位点时，钚的萃取率会降低 2 到 4 倍。紫外-可见光谱显示，这种萃取率的降低是受立体阻碍的影响，导致钚内球络合物被剥夺。立体异构的影响突出表现在离络合位点（α 位）较近的分支上。对映体纯 DEHBA 立体异构体的钚萃取率相似，而立体异构体较杂乱的 (αβ) 异构体的钚萃取率略有下降，同时内球复合物的数量也较少。相反，立体异构体混合物由于在混合复合物中存在拮抗作用，导致钚萃取率大大降低。
• Practical and efficient methods for sulfonylation of alcohols using Ts(Ms)Cl/Et3N and catalytic Me3H·HCl as combined base: Promising alternative to traditional pyridine
  作者：Yoshihiro Yoshida、Yoshiko Sakakura、Naoya Aso、Shin Okada、Yoo Tanabe

  DOI：10.1016/s0040-4020(99)00002-2

  日期：1999.2

  Several alcohols were smoothly and practically tosylated by two methods A and B. Method A uses the TsCl/Et3N (1.5-2.5 equiv)/cat. Me3N . HCl (0.1-1.0 equiv) reagent. Compared with the traditional qr-solvent method, the method A has merits of its much higher reaction rate, operational simplicity, economy in the use of the amine, and circumvention of the undesirable side reaction from R-OTs to R-CL Method B uses TsCl/KOH [or Ca(OH)(2)]/cat. Et3N (0.1 equiv)/cat. Me3N . HCl (0.1 equiv) as the reagent, which will be suited for practical and large scale production for primary alcohols. On both methods A and B, a clear joint action of Et3N and Me3N . HCl catalysts was observed. H-1 NMR measurements support the proposed mechanism of the catalytic cycle. Related methanesulfonylation using Et3N and cat. Me3N . HCl in toluene solvent also successfully proceeded, wherein he clear joint action was also observed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Facile and Practical Methods for the Sulfonylation of Alcohols Using Ts(Ms)Cl and Me2N(CH2)nNMe2 as a Key Base
  作者：Yoshihiro Yoshida

  DOI：10.1055/s-1999-3561

  日期：1999.9
• NOVEL INHIBITORS OF ADENOSINE MONOPHOSPHATE DEAMINASE
  申请人：GENSIA PHARMACEUTICALS, INC.

  公开号：EP0683781A1

  公开（公告）日：1995-11-29