(R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate | 83398-53-2

• 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: (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate
• 英文别名: (R)-3-chloro-2-hydroxypropyl-1-(tolune-4-sulfonate)；(R)-2-hydroxy-3-chloropropyl p-toluenesulfonate；3-chloro-2(R)-hydroxy-1-tosylpropane；(R)-1-chloro-3-tosyloxypropan-2-ol；(R)-3-chloro-2-hydroxy-1-o.tosyl-propanol；[(2R)-3-chloro-2-hydroxypropyl] 4-methylbenzenesulfonate
• CAS: 83398-53-2
• 化学式: C₁₀H₁₃ClO₄S
• 分子量: 264.73
• InChiKey: YCZXDGPMENOKSA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 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：

  (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate 生成 左旋环氧氯丙烷
  参考文献：
  名称：

  化学酶法获得旋光的1,2-环氧化物

  摘要：

  在有机介质中，脂肪酶催化的酰基转移反应被用于生产旋光性的α-羟基甲苯磺酸酯，该α-羟基甲苯磺酸酯可以容易地转化为具有高光学纯度的相应的1,2-环氧化物。

  DOI：

  10.1016/s0040-4039(01)93924-3
• 作为产物：
  描述：

  (R)-2-acetoxy-3-chloropropyl p-toluenesulfonate 以 甲醇 为溶剂， 反应 5.0h， 生成 (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Hamaguchi, Shigeki; Ohashi, Takehisa; Watanabe, Kiyoshi, Agricultural and Biological Chemistry, 1986, vol. 50, # 2, p. 375 - 380

  摘要：

  DOI：

文献信息

• A chemoenzymatic access to optically active 1,2-epoxides
  作者：Ching-Shih Chen、Yeuk-Chuen Liu

  DOI：10.1016/s0040-4039(01)93924-3

  日期：1989.1

  Lipase-catalyzed transacylation in organic media was employed to produce optically active α-hydroxy tosylate which could be readily converted to the corresponding 1,2-epoxides with high optical purity.

  在有机介质中，脂肪酶催化的酰基转移反应被用于生产旋光性的α-羟基甲苯磺酸酯，该α-羟基甲苯磺酸酯可以容易地转化为具有高光学纯度的相应的1,2-环氧化物。
• 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。
• [EN] CHEMICAL COMPOUNDS AS INHIBITORS OF INTERLEUKIN-1 ACTIVITY<br/>[FR] COMPOSÉS CHIMIQUES COMME INHIBITEURS DE L'ACTIVITÉ INTERLEUKINE-1
  申请人：JECURE THERAPEUTICS INC

  公开号：WO2018136890A1

  公开（公告）日：2018-07-26

  The present disclosure relates to novel sulfonylurea and sulfonyl thiourea compounds and related compounds and their use in treating a disease or condition responsive to modulation of cytokines such as IL-1β and IL-18, modulation of NLRP3 or inhibition of the activation of NLRP3 or related components of the inflammatory process.

  本公开涉及新型磺酰脲和磺酰硫脲化合物以及相关化合物，以及它们在治疗对细胞因子如IL-1β和IL-18的调节敏感的疾病或状况中的应用，调节NLRP3或抑制NLRP3或相关炎症过程组分的激活。
• Method for preparing L-carnitine
  申请人：Anic S.p.A.

  公开号：US04413142A1

  公开（公告）日：1983-11-01

  L-carnitine is prepared by a synthesizing process starting from D-mannitol. The synthesis is started with the formation of a D-mannitol ketonide (more specifically D-mannitol acetonide from D-mannitol and acetone, whereafter the D-mannitol is split by oxidation to give glyceraldehyde acetonide, which is further reduced to glycerol acetonide. Then the free hydroxyl group is exchanged with a halogen atom (chlorine) with the formation of chlorodihydroxy propane, the primary alcoholic group of which is functionalized with the acid chloride of a sulfonic acid (tosylchloride). The reaction of the tosyl derivative with the salt of hydrogen cyanide leads to the formation of the corresponding nitrile which, when reacted with trimethylamine gives carnitinonitrile. The nitrile group is now hydrolyzed to give L-carnitine chloride. The formation of L-carnitine can then be obtained by exchanging the chloride ion with a hydroxyl ion.

  左旋肉碱是通过从D-甘露醇开始的合成过程制备的。合成过程始于形成D-甘露醇酮酸酯（更具体地说是D-甘露醇乙酸酯，由D-甘露醇和丙酮反应而成），随后D-甘露醇被氧化分解为甘油醛乙酸酯，进一步还原为甘油醇乙酸酯。然后，游离的羟基团与卤素原子（氯）交换，形成氯二羟基丙烷，其主要醇基与磺酸（对甲苯磺酰氯）的酸氯基发生功能化。磺酸衍生物与氰化氢盐反应形成相应的腈，当与三甲胺反应时生成肉碘腈。腈基现在被水解成左旋肉碱盐酸盐。通过用氢氧根离子交换氯离子，可以得到左旋肉碱的形成。
• Enzymatic method of making 1,2-diol derivatives and their esters with succine anhydride
  申请人：Hwang Ook Soon

  公开号：US20060234362A1

  公开（公告）日：2006-10-19

  The present invention relates to a new process for the preparation of optically active alcohols represented by the general formula 2 and their esters represented by the general formula 3 in scheme 1. In more detail, this invention relates to the process for the preparation of optically active alcohols and their esters which are used as pharmaceutical intermediates by reacting the hydroxyl group stereospecifically by lipase after adding racemic alcohols represented by the general formula 1 and succinic anhydride as an acylating agent to the organic solvent. According to this invention, the primary hydroxyl group of 1,2-diols is transformed by other functional group and the secondary hydroxyl group is esterified stereospecifically with succinic anhydride as an acylating agent. Optically active alcohols and their esters of high optical purity in high yield can be produced by using succinic anhydride as an acylating agent because alcohols can be separated from their esters more easily than those of other conventional methods.

  本发明涉及一种制备光学活性醇的新工艺，其通式为2，以及它们的酯，其通式为3，如图1所示。更详细地说，本发明涉及一种制备光学活性醇及其酯的工艺，通过在有机溶剂中加入通式1的混合醇和琥珀酸酐作为酰化试剂后，通过脂肪酶立体特异性地反应羟基基团。根据本发明，1,2-二醇的主要羟基基团被转化为其他官能团，次要羟基基团通过琥珀酸酐作为酰化试剂被立体特异性地酯化。由于醇可以比其他传统方法更容易地与它们的酯分离，因此可以使用琥珀酸酐作为酰化试剂生产高光学纯度和高收率的光学活性醇及其酯。