(5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione
• 英文别名: (5R,6R)-5,6-dibromocyclohex-2-ene-1,4-dione
• 化学式: C₆H₄Br₂O₂
• 分子量: 267.905
• InChiKey: YVPSGOKCNLXUJP-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 (+)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene
  参考文献：
  名称：

  Enzyme-Assisted Total Synthesis of the Optical Antipodes d-myo-Inositol 3,4,5-Trisphosphate and d-myo-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates

  摘要：

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.

  DOI：

  10.1021/jm981113k
• 作为产物：
  描述：

  对苯醌 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione
  参考文献：
  名称：

  Conduritol-C 和 Conduritol-E 通过对苯醌的新合成

  摘要：

  摘要 从对苯醌 1 开始开发了一种新的 Conduritol-C 8 和 Conduritol-E 13a 立体有择合成方法。通过用 NaBH4 还原二溴对苯醌 2，在这两种合成中都引入了 1,4-氧官能团。2,3-氧官能团通过4的KMnO4氧化引入Conduritol C 8。3与间氯过苯甲酸的氧化得到9。9的酸催化开环反应得到10a，其导致Conduritol-E。

  DOI：

  10.1080/00397919208021660

文献信息

• Concerning the reaction of anti-benzene dioxide with various nucleophiles
  作者：Thomas Esser、Frédéric Farkas、Sissi Mangholz、Urs Séquin

  DOI：10.1016/s0040-4020(01)90392-8

  日期：1994.3

  6-Diepoxycyclohex-1-ene (anti-benzene dioxide) (5) was brought into reaction with several S, O, and C nucleophiles. S and O nucleophiles gave the bis-adducts stemming from independent reaction of the two epoxy functions. C nucleophiles, on the other hand, led to 1,4-addition products. A deuterium labelling experiment showed that BuLi added to the vinyloxirane part of 5 rather than to the conjugated diepoxide

  使反式-3,4：5,6-二环氧环己-1-烯（抗二氧化苯）（5）与几个S，O和C亲核试剂反应。S和O亲核试剂产生了由两个环氧官能团的独立反应产生的双加合物。另一方面，C亲核试剂产生1，4-加成产物。氘标记实验表明，BuLi添加到5的乙烯基环氧乙烷部分中，而不是添加到共轭二环氧官能团上，产生顺式加合物。像预期的那样，铜酸盐主要产生反式产物。
• [EN] LADDERANE LIPID COMPOUNDS AND LIPOSOMES AND METHODS OF PREPARING AND USING THE SAME<br/>[FR] COMPOSÉS LIPIDIQUES DE LADDERANE ET LIPOSOMES ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2018045094A1

  公开（公告）日：2018-03-08

  Methods for preparing a variety of ladderane precursors, ladderane compounds and ladderane lipids are provided. Also provided are methods of preparing a liposome from the ladderane lipids disclosed herein, and compositions thereof. Aspects of the invention include encapsulated one or more cargo moieties in the liposome or compositions thereof and use of the subject liposome compositions as vehicles in drug delivery, imaging, diagnostics and other medical applications. Aspects of the methods disclosed herein include administering a liposomal composition comprising a pharmaceutical agent to a subject under conditions sufficient to deliver the composition to a site of interest in the subject, and release the pharmaceutical agent from the liposomal composition.

  提供了制备各种梯烷前体、梯烷化合物和梯烷脂类的方法。还提供了根据本文披露的梯烷脂类制备脂质体的方法及其组合物。发明的方面包括在脂质体或其组合物中封装一种或多种载荷物质，以及将该脂质体组合物用作药物输送、成像、诊断和其他医疗应用的载体。本文披露的方法的方面包括向受试者施用含有药物剂的脂质体组合物，以在足以将该组合物输送到受试者的感兴趣部位的条件下释放脂质体组合物中的药物剂。
• Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid
  作者：Jaron A. M. Mercer、Carolyn M. Cohen、Steven R. Shuken、Anna M. Wagner、Myles W. Smith、Frank R. Moss、Matthew D. Smith、Riku Vahala、Alejandro Gonzalez-Martinez、Steven G. Boxer、Noah Z. Burns

  DOI：10.1021/jacs.6b10706

  日期：2016.12.14

  producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration

  厌氧氨氧化细菌产生的梯烷脂质构成了生物膜脂质中结构最吸引人但研究很少的分子。生产生物的缓慢生长和纯​​化复杂脂质混合物的固有困难阻碍了有用量的天然梯烷脂质的分离。我们设计了一种高度选择性的梯烷脂尾部和全磷脂酰胆碱的全合成，以实现对这些分子的化学均质样品的生物物理研究。此外，我们报告了天然梯烷的绝对构型的第一个证明。
• Regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol
  作者：Latif Kelebekli、Kadir Aksu、Ertan Şahin

  DOI：10.1016/j.tetlet.2018.02.050

  日期：2018.3

  The regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol is reported. Bromination of p-benzoquinone followed by reduction of the carbonyl groups with NaBH4 gave the corresponding trans-dibromodiol compound, which was reacted with sodium methoxide to produce dimethoxy conduritol-B. Regiospecific bromination of the alkene moiety furnished the desired chiro-inositol

  报道了dl -4，5-二溴-4，5-二脱氧-3，6- O-甲基-手性肌醇的区域和立体有择合成。对-苯醌的溴化，然后用NaBH 4还原羰基，得到相应的反式-二溴二醇化合物，其与甲醇钠反应生成二甲氧基Conduritol-B。烯烃部分的区域特异性溴化提供了所需的手性肌醇衍生物。
• Concise syntheses and some biological activities of <scp>dl</scp> ‐2,5‐di‐ <i>O</i> ‐methyl‐ <i>chiro</i> ‐inositol, <scp>dl</scp> ‐1,4‐di‐ <i>O</i> ‐methyl‐ <i>scyllo</i> ‐inositol, and <scp>dl</scp> ‐1,6‐dibromo‐1,6‐dideoxy‐2,5‐di‐ <i>O</i> ‐methyl‐ <i>chiro</i> ‐inositol
  作者：Kadir Aksu、Hulya Akincioglu、Ilhami Gulcin、Latif Kelebekli

  DOI：10.1002/ardp.202000254

  日期：2021.2

  stereospecific synthesis of O-methyl-chiro-inositols and O-methyl-scyllo-inositol was achieved, starting from p-benzoquinone. After preparing dimethoxy conduritol-B as a key compound, regiospecific bromination of the alkene moiety of dimethoxy conduritol-B and acid-catalyzed ring opening of dimethoxydiacetate conduritol-B epoxide with Ac2 O afforded the desired new chiro-inositol derivatives and scyllo-inositol

  从对苯醌开始，实现了 O-甲基-手性肌醇和 O-甲基-鲨肌醇的区域和立体定向合成。在制备二甲氧基硬糖醇-B作为关键化合物后，二甲氧基硬糖醇-B的烯烃部分的区域特异性溴化和二甲氧基二乙酸硬糖醇-B环氧化物与Ac2O的酸催化开环得到所需的新手性肌醇衍生物和鲨肌醇衍生物， 分别。光谱方法用于表征所有合成的化合物。新型肌醇 (11-17) 对人碳酸酐酶同工酶 I 和 II（hCA I 和 II）以及乙酰胆碱酯酶 (AChE) 具有有效的抑制特性。发现新型肌醇 11-17 是针对 AChE、hCA I 和 hCA II 酶的有效抑制剂。Ki 值的计算范围为 87。hCA I 为 59 ± 7.011 至 237.95 ± 17.75 μM，hCA II 为 65.08 ± 12.39 至 538.98 ± 61.26 μM，A.7Ch 分别为 193.28 ± 43.13 至 765.08 ± 209