2-乙酰氧基丙基甲苯磺酸酯 | 103745-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-乙酰氧基丙基甲苯磺酸酯
• 英文名称: 2-acetoxypropyl tosylate
• 英文别名: (RS)-2-acetyloxy-1-p-toluenesulfonyloxypropane；Propan-1,2-diol-tosylat-acetat；1-(4-Methylphenyl)sulfonyloxypropan-2-yl acetate
• CAS: 103745-04-6
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: JHQPDCMJHLSTTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-乙酰氧基丙基甲苯磺酸酯 生成 (2S)-1-{[(4-methylphenyl)sulfonyl]oxy}propan-2-yl acetate
  参考文献：
  名称：

  PEDERSON, RICHARD L.;LIU, KEVIN K. -C.;RUTAN, JAMES F.;CHEN, LIHREN;WONG,+, J. ORG. CHEM., 55,(1990) N6, C. 4897-4901

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酰氯 在 吡啶 作用下， 反应 10.0h， 生成 2-乙酰氧基丙基甲苯磺酸酯
  参考文献：
  名称：

  Enzymes in organic synthesis: synthesis of highly enantiomerically pure 1,2-epoxy aldehydes, epoxy alcohols, thiirane, aziridine, and glyceraldehyde 3-phosphate

  摘要：

  DOI：

  10.1021/jo00303a026

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。
• Method for producing optically active glycol derivatives
  申请人：Kanegafuchi Kagaku Kogyo Kabushiki Kaisha

  公开号：US04745066A1

  公开（公告）日：1988-05-17

  A method for producing optically active glycol derivatives by biochemical resolution which comprises contacting a racemic ester of the general formula 1 ##STR1## (wherein R.sub.1 is an aliphatic hydrocarbon group of 1 to 16 carbon atoms, R.sub.2 is an aliphatic hydrocarbon group of 1 to 8 carbon atoms, and R.sub.3 is an aromatic hydrocarbon group such as phenyl, tolyl or naphtyl) with a microorganism- or animal organ-derived enzyme having stereoselective hydrolytic activity to asymmetrically hydrolyze said racemic ester of general formula 1 to produce an optically active alcohol of general formula 2* ##STR2## (wherein R.sub.1 and R.sub.3 have the same meanings as defined above) and an unreacted ester of the general formula 1* ##STR3## (wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as defined hereinbefore), separating the optically active compounds from each other, hydrolyzing said ester of general formula 1* to give an optically active glycol derivative which is antipodal to the alcohol of general formula 2* and, then, isolating the same optically active glycol derivative. The invention provides a method for producing optically active glycol derivatives, which is expedient, does not require costly reagents and is suited to commercial scale production.

  一种通过生物化学拆分制备光学活性乙二醇衍生物的方法，包括将一般式1的外消旋酯（其中R.sub.1是1到16个碳原子的脂肪烃基，R.sub.2是1到8个碳原子的脂肪烃基，R.sub.3是芳香烃基，如苯基、甲苯基或萘基）与具有立体选择性水解活性的微生物或动物器官来源的酶接触，使得外消旋酯1按照不对称方式水解成为一般式2*的光学活性醇（其中R.sub.1和R.sub.3的含义与上文定义相同），以及未反应的一般式1*的酯（其中R.sub.1、R.sub.2和R.sub.3的含义如前所述），分离出光学活性化合物，水解所述的一般式1*的酯以得到一种与一般式2*的醇对映的光学活性乙二醇衍生物，然后，分离出相同的光学活性乙二醇衍生物。该发明提供了一种制备光学活性乙二醇衍生物的方法，这种方法方便、不需要昂贵的试剂，并适合商业规模生产。
• 1,3-Dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions
  作者：John A. Bender、Samantha Daves、F.G. West

  DOI：10.1016/s0040-4039(98)00185-3

  日期：1998.4

  Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1,2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1,3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1,3-diol was employed, furan-containing ester

  当在等价的TsOH存在下用1,2-二醇处理时，酰基呋喃3提供了甲苯磺酸化的二醇单酯5。此过程可能通过中间呋喃基缩酮的Protoodefuranation形成1，3-dioxolan-2-ylium阳离子8发生。随后通过对甲苯磺酸的S N 2亲核取代而开环，然后提供酯5。当使用1，3-二醇时，通过表观的醇醛二聚/片段化途径形成了含呋喃的酯9而不是标准产物。
• 4,4-difluoro-1,2,3,4-tetrahydro-5h-1-benzazepine derivative or salt thereof
  申请人：Koshio Hiroyuki

  公开号：US20060122170A1

  公开（公告）日：2006-06-08

  A novel 4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivative or a pharmaceutically acceptable salt thereof, which is useful as an agent for treating or preventing nocturia and/or diabetes insipidus, is provided.

  提供一种新型的4,4-二氟-1,2,3,4-四氢-5H-1-苯并嗪衍生物或其药学上可接受的盐，该衍生物可用作治疗或预防夜尿症和/或尿崩症的药物。
• 4,4-Difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivative or salt thereof
  申请人：Koshio Hiroyuki

  公开号：US20070167429A1

  公开（公告）日：2007-07-19

  A novel 4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivative or a pharmaceutically acceptable salt thereof, which is useful as an agent for treating or preventing nocturia and/or diabetes insipidus, is provided.

  提供了一种新型的4,4-二氟-1,2,3,4-四氢-5H-1-苯并氮杂环衍生物或其药学上可接受的盐，该衍生物在治疗或预防夜尿症和/或尿崩症方面有用。