ethyl-1,1-d2 alcohol 4-methylbenzenesulfonate | 60835-92-9

• 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: ethyl-1,1-d2 alcohol 4-methylbenzenesulfonate
• 英文别名: toluene-4-sulfonic acid 1,1-dideuterio-ethyl ester；1,1-d2-ethyl tosylate；1,1-Dideuterioethyl 4-methylbenzenesulfonate
• CAS: 60835-92-9
• 化学式: C₉H₁₂O₃S
• 分子量: 202.243
• InChiKey: VRZVPALEJCLXPR-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  ethyl-1,1-d2 alcohol 4-methylbenzenesulfonate 生成 乙烯-1,1-D2
  参考文献：
  名称：

  The Synthesis of [2-2H1]Thiirane-1-oxide and [2,2-2H2]Thiirane-1-oxide and the Diastereoselective Infrared Laser Chemistry of [2-2H1]Thiirane-1-oxide

  摘要：

  We report the synthesis of the title compounds CH2CHDSO and CH2CD2SO and their characterization by infrared spectroscopy. The monodeuterated species occurs in two isotopically diastereomeric forms with the D atom either cis or trans oriented to the O atom, The SO infrared chromophore in these diastereomers has a strong absorption centered near 1114 and 1116 cm(-1), respectively, with an integrated band strength G = 2.8 pm(2), which renders it very suitable for infrared multiphoton excitation with a CO2 laser, leading to the laser chemical dissociation of the reactants into deuterated ethylene and SO((3) Sigma(-)). We have established the first successful laser chemical separation of such a diastereomer pair, with a small but significant separation factor based on the small frequency difference of the v(4) (SO stretching) fundamental mentioned above; the analysis used high-resolution FTIR spectroscopy in the region of the Q branches of v(4). Our results are discussed in relation to various aspects of stereochemical reaction dynamics in chiral and achiral sulfoxides.

  DOI：

  10.1002/(sici)1521-3765(19980310)4:3<441::aid-chem441>3.0.co;2-3
• 作为产物：
  描述：

  乙醇-1,1-D2 、 对甲苯磺酰氯 在 sodium hydride 作用下， 以68%的产率得到ethyl-1,1-d2 alcohol 4-methylbenzenesulfonate
  参考文献：
  名称：

  晶体学研究异青霉素N合酶对选择性氘代LLD和LLL底物差向异构体的结合。

  摘要：

  异青霉素N合酶（IPNS）是一种非血红素铁（II）氧化酶，可催化三肽δ-1-α-氨基己二酰基-1-半胱氨酰-d-缬氨酸（lld-ACV）的生物合成。本文中我们报道了晶体学研究，以研究IPNS活性位点中截短的III-底物的结合。通过溶液相肽合成已经制备了两种表位三肽，并用该酶结晶。δ-1-α-氨基己二酰基-1-半胱氨酰-d-2-氨基-3,3-二氘代丁二酸酯（lld-ACd（2）Ab）在其三个立体中心分别具有与天然底物lld-ACV相同的构型；它的差向异构体δ-1-α-氨基己二酰基-1-半胱氨酰基-1--2-氨基-3,3-二氘代丁二酸酯（III-ACd（2）Ab）在其第三个氨基酸处具有相反的构型。先前已显示III-ACV抑制其底物IId-ACV的IPNS转换。全精制的三肽δ-1-α-氨基己二酰基-1-半胱氨酸-d-2-氨基丁酸酯（lld-ACAb）是IPNS的底物，被转化为Penam和Ceph

  DOI：

  10.1016/j.bbrc.2010.06.129

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR COGNITION-ENHANCEMENT, METHODS OF MAKING, AND METHODS OF TREATING<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR AMÉLIORER LA FONCTION COGNITIVE, PROCÉDÉS DE FABRICATION ET MÉTHODES DE TRAITEMENT
  申请人：MITHRIDION INC

  公开号：WO2010102218A1

  公开（公告）日：2010-09-10

  Muscarinic agonists, which are useful for stimulating muscarinic receptors and treating cognitive disorders, are provided. Methods of synthesizing such agonists also are provided. Also provided are compositions for enhancing cognitive function in subjects such as humans, the compositions comprising a muscarinic agonist or a pharmaceutically suitable form thereof. Also provided are methods of treating animals such as humans by administering such compositions.

  提供了用于刺激肌气受体并治疗认知障碍的肌气受体激动剂。还提供了合成这类激动剂的方法。还提供了用于增强人类等受试者认知功能的组合物，该组合物包括肌气受体激动剂或其药用适宜形式。还提供了通过给予这类组合物来治疗动物如人类的方法。
• β-d2烷基酸类化合物的制备方法
  申请人：凯莱英生命科学技术(天津)有限公司

  公开号：CN108101771A

  公开（公告）日：2018-06-01

  本发明提供了一种β‑d2烷基酸类化合物的制备方法。该制备方法包括以下步骤：将化合物A和LiAlD4还原反应，得到化合物B；对化合物B进行‑OD基保护反应，得到中间体C；对中间体C进行溴代反应，得到化合物D；以及在碱性条件下将化合物D与乙酸进行取代反应，得到β‑d2烷基酸类化合物。该方法以廉价易得的烃基酸为起始原料，依次经LiAlD4还原反应、‑OD基保护反应、溴代反应、乙酸取代反应四步制得了β‑d2烷基酸类化合物。该法工艺路线简单，且反应过程中无需采用昂贵的催化剂等原料，成本较低。而且，利用本发明的制备方法，β‑d2烷基酸类化合物的总收率较高，反应放大至克级收率稳定，重复性好，实用可行。
• [EN] COMPOUNDS AND COMPOSITIONS FOR COGNITION-ENHANCEMENT, METHODS OF MAKING, AND METHODS OF TREATING<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR L'AMÉLIORATION DE LA COGNITION, LEURS PROCÉDÉS DE FABRICATION, ET MÉTHODES DE TRAITEMENT
  申请人：MITHRIDION INC

  公开号：WO2011085406A1

  公开（公告）日：2011-07-14

  Disclosed are muscarinic agonist compounds including oxadiazole derivatives, compositions and preparations thereof. Also disclosed are methods of synthesizing such oxadiazole compounds. Further disclosed are methods for treating a subject with said muscarinic agonists or a pharmaceutically suitable form thereof to enhance cognitive function.

  揭示了包括噻唑二唑衍生物在内的肌碱激动剂化合物，以及其组合物和制剂。还揭示了合成这种噻唑二唑化合物的方法。进一步揭示了使用这些肌碱激动剂或其药学适宜形式来增强认知功能的治疗方法。
• [EN] COGNITION ENHANCING COMPOUNDS AND COMPOSITIONS, METHODS OF MAKING, AND METHODS OF TREATING<br/>[FR] COMPOSÉS ET COMPOSITIONS AMÉLIORANT LA COGNITION, MÉTHODES DE PRÉPARATION ET MÉTHODES DE TRAITEMENT
  申请人：MITHRIDION INC

  公开号：WO2012033956A1

  公开（公告）日：2012-03-15

  The invention relates generally to muscarinic agonists, which are useful for stimulating muscarine, receptors and treating cognitive disorders. Included among the muscarinic agonists disclosed herein are oxadiazole derivatives compositions, and preparations thereof. Methods of synthesizing oxadiazole compounds also are provided. This disclosure also relates in part to compositions for enhancing cognitive function in subjects such as humans. The compositions comprising a muscarinic agonist or a pharma.ceutically suitable form thereof. This disclosure relates in part to methods of treating animals such as humans by administering such compositions.

  该发明通常涉及对可用于刺激肌碱受体和治疗认知障碍的肌碱激动剂。本文披露的肌碱激动剂包括噁唑二唑衍生物组合物及其制剂。还提供了合成噁唑二唑化合物的方法。本公开还涉及部分用于增强诸如人类等受试者认知功能的组合物。该组合物包括肌碱激动剂或其药学适宜形式。本公开还涉及通过给予这种组合物来治疗动物如人类的方法。
• Crystallographic studies on the binding of selectively deuterated LLD- and LLL-substrate epimers by isopenicillin N synthase
  作者：Wei Ge、Ian J. Clifton、Jeanette E. Stok、Robert M. Adlington、Jack E. Baldwin、Peter J. Rutledge

  DOI：10.1016/j.bbrc.2010.06.129

  日期：2010.8

  we report crystallographic studies to investigate the binding of a truncated lll-substrate in the active site of IPNS. Two epimeric tripeptides have been prepared by solution phase peptide synthesis and crystallised with the enzyme. delta-l-alpha-Aminoadipoyl-l-cysteinyl-d-2-amino-3,3-dideuteriobutyrate (lld-ACd(2)Ab) has the same configuration as the natural substrate lld-ACV at each of its three stereocentres;

  异青霉素N合酶（IPNS）是一种非血红素铁（II）氧化酶，可催化三肽δ-1-α-氨基己二酰基-1-半胱氨酰-d-缬氨酸（lld-ACV）的生物合成。本文中我们报道了晶体学研究，以研究IPNS活性位点中截短的III-底物的结合。通过溶液相肽合成已经制备了两种表位三肽，并用该酶结晶。δ-1-α-氨基己二酰基-1-半胱氨酰-d-2-氨基-3,3-二氘代丁二酸酯（lld-ACd（2）Ab）在其三个立体中心分别具有与天然底物lld-ACV相同的构型；它的差向异构体δ-1-α-氨基己二酰基-1-半胱氨酰基-1--2-氨基-3,3-二氘代丁二酸酯（III-ACd（2）Ab）在其第三个氨基酸处具有相反的构型。先前已显示III-ACV抑制其底物IId-ACV的IPNS转换。全精制的三肽δ-1-α-氨基己二酰基-1-半胱氨酸-d-2-氨基丁酸酯（lld-ACAb）是IPNS的底物，被转化为Penam和Ceph