4,5-dimethylethylene (cis,trans) sulphite | 4440-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 4,5-dimethylethylene (cis,trans) sulphite
• 英文别名: (+/-)-1,2-Dimethylethylensulfit；(+/-)-threo-1.2-Dimethyl-aethylenglykol-sulfit；4r,5t-dimethyl-[1,3,2]dioxathiolane 2-oxide；O²,O³-sulfinyl-DL-1,4-dideoxy-threitol；(4S,5S)-4,5-dimethyl-1,3,2-dioxathiolane 2-oxide
• CAS: 4440-90-8；24212-85-9；40811-17-4；40811-18-5；40934-47-2；51260-44-7；51260-47-0
• 化学式: C₄H₈O₃S
• 分子量: 136.172
• InChiKey: SAPINXZHMGNTEC-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P201,P264,P280,P302+P352+P312,P304+P340+P312
• 危险性描述：
  H302+H312+H332,H341

反应信息

• 作为反应物：
  描述：

  4,5-dimethylethylene (cis,trans) sulphite 在 ruthenium trichloride 、 sodium periodate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到(4S,5S)-4,5-dimethyl-1,3,2-dioxathiolane 2,2-dioxide
  参考文献：
  名称：

  Effect of Methyl Substitution on Conformation and Molecular Arrangement of BEDT-TTF Derivatives in the Crystalline Environment

  摘要：

  立体选择性合成了两种甲基化双(乙撑二硫)四硫富瓦烯 (ET) 衍生物 Me2ET 和 Me4ET，以研究甲基化对二氢二硫环构象和结晶态分子排列的影响。由于Me2ET和Me4ET的供体能力与ET相似，因此甲基化的ET衍生物被认为适合通过改变供体分子的体积来研究对ET自由基盐的“晶格压力”效应。通过 13C NMR 光谱估计溶液中二甲基化二氢二硫因环反转的活化能上限为 32 kJ mol−1。 X射线结构分析表明，Me2ET中甲基的取向固定为轴向，Me4ET中甲基的取向固定为赤道，并伴随着分子堆积的变化。通过比较Me2ET和Me4ET与ET的分子体积来评估“甲基的体积”，结果发现轴向甲基的有效体积比赤道上的有效体积大15%。 ET及其衍生物的固态13C NMR（CP/MAS）谱表明，共振线的化学位移反映了晶体中二氢二硫因环的构象。

  DOI：

  10.1246/bcsj.66.513
• 作为产物：
  描述：

  (2S,3S)-(+)-2,3-丁二醇 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 4,5-dimethylethylene (cis,trans) sulphite
  参考文献：
  名称：

  二氢马尼瓦霉素 E，一种来自耐热链霉菌属的热休克代谢物。 JA74，对流感和 SARS-CoV-2 病毒表现出抗病毒活性

  摘要：

  二氢马尼瓦霉素 E ( 1 ) 是一种新型马尼瓦霉素衍生物，具有氧化偶氮基部分，是从耐热链霉菌的培养物提取物中分离出来的。 JA74 以及已知的类似物马尼瓦霉素 E ( 2 )。化合物1只能通过菌株JA74在45°C下培养来产生，这种类型的化合物之前被我们的研究小组指定为“热休克代谢物（HSM）”。化合物2在高温下被检测为产量增强的代谢物。 1和2的结构通过NMR和MS光谱分析得到阐明。四种立体异构体全合成后确定1的绝对结构。虽然2的绝对结构被认为与马尼瓦霉素D的结构相同，但2的NMR和旋光值与马尼瓦霉素E的一致。因此，本研究提出对马尼瓦霉素D和马尼瓦霉素D的结构进行修正。 E.化合物1和2显示出针对MDCK细胞的流感(H1N1)病毒感染的抑制活性，显示IC 50值分别为25.7和63.2μM。值得注意的是，当用于感染 293TA 和 VeroE6T 细胞时， 1和2显示出针对 SARS-CoV-2（COVID-19

  DOI：

  10.1021/acs.jnatprod.2c00550

文献信息

• MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME
  申请人：Hoveyda Hamid

  公开号：US20080194672A1

  公开（公告）日：2008-08-14

  The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，可以作为生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、骨骼疾病、遗传疾病、过度增生性疾病和炎症性疾病。
• Aluminum-Catalyzed Formation of Functional 1,3,2-Dioxathiolane 2-Oxides from Sulfur Dioxide: An Easy Entry towards<i>N</i>-Substituted Aziridines
  作者：Victor Laserna、Eddy Martin、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/adsc.201600831

  日期：2016.12.7

  Aluminum(III) complexes derived from aminotriphenolate ligands are shown to be excellent catalysts for the formation of cyclic sulfites from a range of (functionalized) terminal and internal epoxides, and ex situ generated sulfur dioxide. The developed catalytic protocol is characterized by its operational simplicity, wide scope in epoxide reaction partners, good to excellent isolated yields and mild

  已显示衍生自氨基三酚盐配体的铝（III）络合物是出色的催化剂，可用于从一系列（官能化的）末端和内部环氧化物形成环亚硫酸盐，并在异位生成二氧化硫。发达的催化方案的特点是操作简单，在环氧化物反应伙伴中适用范围广，分离产率好至极好以及反应条件温和[50-70°C，p（SO 2）<1 bar]。这些环状亚硫酸盐在有机合成中的合成潜力通过三步操作流程在N取代的氮丙啶的制备中得到了证明。
• Effect of Methyl Substitution on Conformation and Molecular Arrangement of BEDT-TTF Derivatives in the Crystalline Environment
  作者：Shigeki Matsumiya、Akira Izuoka、Tadashi Sugawara、Tomohiro Taruishi、Yuzo Kawada

  DOI：10.1246/bcsj.66.513

  日期：1993.2

  Two methylated bis(ethylenedithio)tetrathiafulvalene (ET) derivatives, Me2ET and Me4ET were stereoselectively synthesized to examine the effect of methylation on conformations of dihydrodithiin rings and molecular arrangements in the crystalline state. Since the donating ability of Me2ET and Me4ET are similar to that of ET, the methylated ET derivatives are considered to be appropriate to investigate the “lattice pressure” effect on ET radical salts by changing the volume of donor molecules. The upper limit of an activation energy for the ring inversion of the dimethylated dihydrodithiin in solution was estimated to be 32 kJ mol−1 by 13C NMR spectroscopy. The X-ray structure analyses revealed that orientations of methyl groups are fixed to axial in Me2ET and to equatorial in Me4ET, accompanied by the change of molecular stacking. The “volume of a methyl group” was evaluated by comparing the molecular volumes of Me2ET and Me4ET with that of ET, and the effective volume for the axial methyl group turns out to be 15% larger than that of the equatorial. The solid state 13C NMR (CP/MAS) spectra of ET and its derivatives showed that the chemical shifts of resonance lines reflect the conformations of dihydrodithiin rings in crystals.

  立体选择性合成了两种甲基化双(乙撑二硫)四硫富瓦烯 (ET) 衍生物 Me2ET 和 Me4ET，以研究甲基化对二氢二硫环构象和结晶态分子排列的影响。由于Me2ET和Me4ET的供体能力与ET相似，因此甲基化的ET衍生物被认为适合通过改变供体分子的体积来研究对ET自由基盐的“晶格压力”效应。通过 13C NMR 光谱估计溶液中二甲基化二氢二硫因环反转的活化能上限为 32 kJ mol−1。 X射线结构分析表明，Me2ET中甲基的取向固定为轴向，Me4ET中甲基的取向固定为赤道，并伴随着分子堆积的变化。通过比较Me2ET和Me4ET与ET的分子体积来评估“甲基的体积”，结果发现轴向甲基的有效体积比赤道上的有效体积大15%。 ET及其衍生物的固态13C NMR（CP/MAS）谱表明，共振线的化学位移反映了晶体中二氢二硫因环的构象。
• [EN] BENZAMIDE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ BENZAMIDE ET SON UTILISATION<br/>[ZH] 苯甲酰胺类化合物及其用途
  申请人：WUHAN HUMANWELL INNOVATIVE DRUG RES AND DEVELOPMENT CENTER LIMITED COMPANY

  公开号：WO2022068930A1

  公开（公告）日：2022-04-07

  涉及一种有效拮抗P2X3受体的新化合物，其为式（I）所示化合物、其互变异构体、立体异构体、水合物、溶剂化物、药学上可接受的盐或前药，其制备方法，以及其在制备药物中的用途。
• Chirality Driven Metallic versus Semiconducting Behavior in a Complete Series of Radical Cation Salts Based on Dimethyl-Ethylenedithio-Tetrathiafulvalene (DM-EDT-TTF)
  作者：Flavia Pop、Pascale Auban-Senzier、Arkadiusz Frąckowiak、Krzysztof Ptaszyński、Iwona Olejniczak、John D. Wallis、Enric Canadell、Narcis Avarvari

  DOI：10.1021/ja408350r

  日期：2013.11.13

  Enantiopure (S,S) and (R,R) dimethyl-ethylenedithio-tetrathiafulvalene (DM-EDT-TTF) 1 donors are synthesized by cross coupling followed by decarboxylation reactions. In the solid state the methyl groups are arranged in axial positions within sofa-type conformation for the six-membered rings. Crystalline radical cation salts formulated as [(S,S)-1](2)PF6, [(R,R)-1](2)PF6, and [(rac)-1](2)PF6 are obtained by electrocrystallization. When the experiment is conducted with enantioenriched mixtures both enantiopure and racemic phases are obtained. The monoclinic enantiopure salts, containing four independent donors in the unit cell, show semiconducting behavior supported by band structure calculations of extended Hiickel type. The racemic salt contains only one independent donor in the mixed valence oxidation state +0.5. Under ambient pressure the racemic material is metallic down to 120 K, while an applied pressure of 11.5 kbar completely suppresses the metal insulator transition. Band structure calculations yield an open Fermi surface, typical for a pseudo-one-dimensional metal, with unperfected nesting, thus ruling out the possibility of charge or spin density modulations to be at the origin of the transition. Raman spectroscopy measurements, in agreement with structural analysis at 100 K, show no indication of low-temperature charge ordering in the racemic material at ambient pressure, thus suggesting Mott-type charge localization for the observed metal insulator transition.