2-hydroxy-1-methylethyl 4-toluenesulfonate | 54619-27-1

• 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: 2-hydroxy-1-methylethyl 4-toluenesulfonate
• 英文别名: 2-(4-Methylbenzenesulfonyloxy)-1-propanol；1-Hydroxyprop-2-yltosylat；1-Hydroxypropan-2-yl 4-methylbenzenesulfonate
• CAS: 54619-27-1
• 化学式: C₁₀H₁₄O₄S
• 分子量: 230.285
• InChiKey: UADUJNAWMVEFHR-UHFFFAOYSA-N

物化性质

• 沸点：
  379.5±25.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-hydroxy-1-methylethyl 4-toluenesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到2-Azido-1-propanol
  参考文献：
  名称：

  The regioselective and stereospecific substitution of unsymmetrical 1,2-diols using the 1,3,2λ5-dioxaphospholane methodology.

  摘要：

  Stereospecific tosylate (-OTs) or azide (N3-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2-lambda-5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either p-toluenesulfonic acid (p-TsOH) in tetrahydrofuran solvent or p-TsOH/sodium azide in acetonitrile solvent, respectively.

  DOI：

  10.1016/s0040-4020(01)96904-2
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl ester 在 甲醇 、 溴 作用下， 反应 1.0h， 以94%的产率得到2-hydroxy-1-methylethyl 4-toluenesulfonate
  参考文献：
  名称：

  Bromine in Methanol: An Efficient Reagent for the Deprotection of the tert-Butyldiphenylsilyl Group

  摘要：

  介绍了一种选择性试剂，该试剂在回流条件下使用溴在甲醇中的溶液，对存在其他保护基团的叔丁基二苯基硅烷（TBDPS）醚进行脱保护。此外，该试剂还可用于 TBDPS 胺和酯的脱保护，并在去除存在 TBDPS 的 TBDMS 醚时显示出良好的选择性。

  DOI：

  10.1055/s-2001-15136

文献信息

• Benzoxaborole Catalyst for Site-Selective Modification of Polyols
  作者：Shuhei Kusano、Shoto Miyamoto、Aki Matsuoka、Yuji Yamada、Ryuta Ishikawa、Osamu Hayashida

  DOI：10.1002/ejoc.201901749

  日期：2020.3.22

  Novel benzoxaborole derivatives were designed as efficient catalysts for the highly site‐selective and protecting‐group‐free modification of polyols, such as carbohydrate. Additionally, the benzoxaborole catalyst could tolerate diverse modifications of polyols, including acylation, sulfonylation, alkylation, and glycosylation.

  新型苯并氧杂硼杂环戊烷衍生物被设计为多元醇（例如碳水化合物）的高度位点选择性和无保护基团修饰的有效催化剂。另外，苯并氧杂硼烷催化剂可耐受多元醇的多种改性，包括酰化，磺酰化，烷基化和糖基化。
• [EN] SYNTHESIS OF INTERMEDIATES USED IN THE MANUFACTURE OF ANTI-HIV AGENTS<br/>[FR] SYNTHÈSE D'INTERMÉDIAIRES UTILISÉS DANS LA FABRICATION D'AGENTS ANTI-VIH
  申请人：CBZ INVEST LTD

  公开号：WO2016178162A1

  公开（公告）日：2016-11-10

  The present invention relates to a process of preparing intermediates of Formula (I). The process comprises of reacting compound of Formula (III) with compound of Formula (V) in the presence of a solvent selected from an alcohol, ether or water to form compound of Formula (I) wherein, R1 is selected from –NH2, Cl, Br, NHCOR", wherein R" is alkyl, aryl, Schiff's base of formula N=CHR', wherein R' is alkyl or aryl; R2 is selected from H, alkyl; R3 and R4, each independently is H; R5 and R6, each independently is H, alkyl; R7 is H, alkyl; and R8 is H, alkyl.

  本发明涉及一种制备公式（I）中间体的方法。该方法包括在醇，醚或水中选择的溶剂的存在下，将公式（III）化合物与公式（V）化合物反应，形成公式（I）化合物，其中，R1从-NH2，Cl，Br，NHCOR“中选择，其中R”是烷基，芳基，公式N = CHR'的Schiff碱，其中R'是烷基或芳基；R2从H，烷基中选择；R3和R4各自独立地是H；R5和R6各自独立地是H，烷基；R7是H，烷基；R8是H，烷基。
• Gudkova,A.S. et al., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, # 12, p. 2529 - 2531
  作者：Gudkova,A.S. et al.

  DOI：——

  日期：——
• Zefirov, N. S.; Kirin, V. N.; Yur'eva, N. M., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1264 - 1279
  作者：Zefirov, N. S.、Kirin, V. N.、Yur'eva, N. M.、Zhdankin, V. V.、Kozmin, A. S.

  DOI：——

  日期：——
• Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine
  作者：Yasutaka Shimada、Kazumasa Usuda、Hirokazu Okabe、Tsuguru Suzuki、Kazutsugu Matsumoto

  DOI：10.1016/j.tetasy.2009.11.005

  日期：2009.12

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.