(R)-1-(4-甲基苯磺酸酯基)-1,2-丁二醇 | 103745-07-9

• 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: (R)-1-(4-甲基苯磺酸酯基)-1,2-丁二醇
• 英文名称: (R)-(+)-2-hydroxybutyl tosylate
• 英文别名: (R)-2-Hydroxybutyl tosylate；[(2R)-2-hydroxybutyl] 4-methylbenzenesulfonate
• CAS: 103745-07-9
• 化学式: C₁₁H₁₆O₄S
• 分子量: 244.312
• InChiKey: UVSOURZMHXZMJW-SNVBAGLBSA-N

物化性质

• 沸点：
  357.23°C (rough estimate)
• 密度：
  1.2976 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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)-1-(4-甲基苯磺酸酯基)-1,2-丁二醇 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醚 为溶剂， 反应 0.5h， 以81%的产率得到(R)-octan-3-ol
  参考文献：
  名称：

  Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols

  摘要：

  2,3-epoxy alcohols-1-tosylates are regio and chemoselectively opened to the corresponding 3-halohydrins (I, Br, Cl): the reduction of the iodohydrins to the monoprotected diols and subsequent standard coupling of the tosyl group leads to a straightforward synthesis of optically active naturally occurring pheromones.

  DOI：

  10.1016/s0040-4039(00)75820-5
• 作为产物：
  描述：

  trans-2-(p-Toluenesulfonyloxymethyl)-3-methyloxirane 在 Amberlyst 15 、 偶氮二异丁腈 、 三正丁基氢锡 、 lithium iodide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 (R)-1-(4-甲基苯磺酸酯基)-1,2-丁二醇
  参考文献：
  名称：

  Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols

  摘要：

  2,3-epoxy alcohols-1-tosylates are regio and chemoselectively opened to the corresponding 3-halohydrins (I, Br, Cl): the reduction of the iodohydrins to the monoprotected diols and subsequent standard coupling of the tosyl group leads to a straightforward synthesis of optically active naturally occurring pheromones.

  DOI：

  10.1016/s0040-4039(00)75820-5

文献信息

• Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
  作者：K. Matsumoto、K. Oohana、M. Hashimoto、K. Usuda、T. Shimoda、H. Ohshima、Y. Suzuki、T. Togawa

  DOI：10.1016/j.tet.2018.05.087

  日期：2018.7

  We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction

  我们已经成功地通过酶水解容易地制备了带有不饱和取代基的光学活性的1,2-二醇单甲苯磺酸酯。脂肪酶PS快速催化具有双键的2-乙酰氧基丁-3-烯基甲苯磺酸酯和具有三键的2-乙酰氧基丁-3-炔基甲苯磺酸酯的水解，具有出色的对映选择性，可提供相应的旋光化合物。该反应也适用于在末端具有双键的较长链的乙酸酯。为了证明该方法的适用性，已从外消旋的2-乙酰氧基戊-4-烯基甲苯磺酸酯中分几步合成了对映体纯的（R）-马苏阿内酯，一种天然椰子香精。此外，该酶可以识别烯烃的立体化学，而（Z）-烯基结构比（E）-异构体更适合于对映选择性水解。
• Tetrahydroimidazo(1,5-D)[1,4]Oxazepine Derivative
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20140243316A1

  公开（公告）日：2014-08-28

  A compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof works as an mGluR2 antagonist, and is applicable as a therapeutic agent for neurological disorders related to glutamate dysfunction and diseases involving the mGluR2, such as Alzheimer's disease: wherein R is a hydrogen atom, a C 1-6 alkyl group or the like, R 1 is a C 1-6 alkyl group, a C 1-6 alkoxy group or the like, R 2 is a halogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group or the like, R 3 is a hydrogen atom, a C 1-6 alkyl group or the like, and R 4 is a C 1-6 alkyl group or the like.

  以下公式（I）表示的化合物或其药用可接受盐作为mGluR2拮抗剂，可用作治疗与谷氨酸功能障碍相关的神经疾病和涉及mGluR2的疾病，如阿尔茨海默病：其中R是氢原子、C1-6烷基或类似物，R1是C1-6烷基、C1-6甲氧基或类似物，R2是卤素原子、C1-6烷基、C1-6甲氧基或类似物，R3是氢原子、C1-6烷基或类似物，R4是C1-6烷基或类似物。
• 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。
• Enzymatic method of making 1,2-diol derivatives and their esters
  申请人：Hwang Ook Soon

  公开号：US20070026508A1

  公开（公告）日：2007-02-01

  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 by enzymatic method from racemic alcohols represented by the general formula 1 in scheme 1. In more details, this invention relates to a process for producing optically active alcohols and their esters which are used as pharmaceutical intermediates from alcohols represented by the general formula 1 by stereospecific transesterification of secondary hydroxyl group using lipases as catalyst with acyl donors in organic solvent or with acyl donors only without using organic solvent. According to this invention, optically active alcohols and esters of high optical purity in high yield can be produced by transforming the primary hydroxyl group of 1,2-diols by tosyl group and transesterifying the secondary hydroxyl group stereospecifically by lipase.

  本发明涉及一种新的方法，通过酶法从通式1所表示的外消旋醇制备通式2所表示的光学活性醇及其酯，通式3。更详细地说，本发明涉及一种从通式1所表示的醇中，使用脂肪酶作为催化剂，通过立体特异性转酯化反应转化次级羟基，使用有机溶剂或仅使用酰基供体而不使用有机溶剂，生产用作制药中间体的光学活性醇及其酯的方法。根据本发明，通过将1,2-二醇的主要羟基转化为对甲苯磺酰基，并通过脂肪酶立体特异性地转酯化次级羟基，可以生产高产率的高光学纯度的光学活性醇和酯。
• Process for the enzymatic separation of the optical isomers of tosyloxy-alkanols
  申请人：MINISTERO DELL' UNIVERSITA' E DELLA RICERCA SCIENTIFICA E TECNOLOGICA

  公开号：EP0490407A2

  公开（公告）日：1992-06-17

  Described is a process for the biotechnological resolution, by means of stereoselective enzymatic esterification, of the racemic mixture of optical isomers of tosyloxy-alkanols of general formula (I): wherein R represents an alkyl, haloalkyl or C2-Cio alkenyl group, either linear or branched, and n is 1 or 2, by using aliphatic acid anhydrides in the presence of an enzyme which is capable of selectively catalyzing the esterification of the (R) isomer, leaving the (S) isomer basically unchanged.

  本发明描述了一种通过立体选择性酶法酯化，以生物技术解决通式(I)的对羟基烷 醇光学异构体外消旋混合物的工艺： 其中 R 代表直链或支链烷基、卤代烷基或 C2-Cio 烯基，n 为 1 或 2，使用脂肪族酸酐，在一种酶的存在下，该酶能选择性地催化（R）异构体的酯化反应，而（S）异构体基本不变。