(2R)-(-)-3,3-dimethylbutane-1,2,4-triol | 60856-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-(-)-3,3-dimethylbutane-1,2,4-triol
• 英文别名: (R)-(-)-3,3-dimethyl-1,3,4-butanetriol；(2R)-3,3-dimethylbutane-1,2,4-triol；(S)-3,3-dimethyl-1,2,4-butanetriol；2,2-dimethylbutan-1,3,4-triol；(R)-3,3-dimethyl-butane-1,2,4-triol；(R)-3,3-dimethylbutane-1,2,4-triol
• CAS: 60856-63-5
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: SJTKQIPAACOOGS-YFKPBYRVSA-N

物化性质

• 熔点：
  55-57 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  286.2±20.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-(-)-3,3-dimethylbutane-1,2,4-triol 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium azide 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 74.34h， 生成 ethyl 7-[(4S)-4-amino-3,3-dimethylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028
• 作为产物：
  描述：

  D-(-)-泛酰内酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以51.0 g的产率得到(2R)-(-)-3,3-dimethylbutane-1,2,4-triol
  参考文献：
  名称：

  An Effective Method for the Preparation of Chiral Polyoxy 8-Membered Ring Enone Corresponding to the B Ring of Taxol

  摘要：

  开发了一种有效制备八元环烯酮(4S,5R,7R,8R)-4,8-二(苄氧基)-7-(叔丁基二甲基硅氧基)-5-(4-甲氧基苄氧基)-2,6,6-三甲基环辛-2-烯酮(1)的方法，可获得足量产物。首先，通过对(2R,4S)-2-(4-甲氧基苯基)-5,5-二甲基-4-乙烯基-1,3-二氧六环进行非对映选择性二羟基化反应，制备了光学活性三氧基醛(3R,4S)-4-苄氧基-5-(叔丁基二甲基硅氧基)-3-(4-甲氧基苄氧基)-2,2-二甲基戊醛(3)，该化合物源自D-乳酸内酯。随后，通过以下反应新合成了8-氯-7-氧代醛(2R,3R,5R,6R)-2,6-二(苄氧基)-5-(叔丁基二甲基硅氧基)-8-氯-3-(4-甲氧基苄氧基)-4,4-二甲基-7-氧代壬醛(30)：i)镁溴化物•OEt2介导的醛3与(Z)-2-苄氧基-1-甲氧基-1-(三甲基硅氧基)乙烯的非对映选择性羟醛反应，以及ii)甲基(2R,3R,5R,6S)-2,6-二(苄氧基)-3,7-二(叔丁基二甲基硅氧基)-5-(4-甲氧基苄氧基)-4,4-二甲基庚酸酯与1,1-二氯乙基锂的反应，接着通过1,1-二氯乙基锂连续还原脱卤，生成1,1-二氯乙基酮。最后，通过SmI2介导的羟醛环化反应，将手性的8-氯-7-氧代醛30转化为八元环烯酮1。

  DOI：

  10.1246/bcsj.74.113

文献信息

• DIURETICS
  申请人：ALI Amjad

  公开号：US20100029678A1

  公开（公告）日：2010-02-04

  A compound having the structure wherein X is selected from the group consisting of: a bond, —NHCH 2 (CH 2 ) n CH 2 OC(O)—, —CH 2 NHC(O)CH 2 NHC(O)—, —CH 2 OC(O)—, —OCH(CH 3 )OC(O)—, —OCH 2 OC(O)—, —O—, —NR 1 —, —CR 1 R 3 —, —(CH 2 ) p —, —(CH 2 ) q NR 1 C(O)—, —CHR 5 NR 2 C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)NR 1 —, or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating, hypertension.

  具有以下结构的化合物： 其中 X 是从以下组中选择： 一个键，—NHCH 2 (CH 2 ) n CH 2 OC(O)—, —CH 2 NHC(O)CH 2 NHC(O)—, —CH 2 OC(O)—, —OCH(CH 3 )OC(O)—, —OCH 2 OC(O)—, —O—, —NR 1 —, —CR 1 R 3 —, —(CH 2 ) p —, —(CH 2 ) q NR 1 C(O)—, —CHR 5 NR 2 C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)NR 1 —， 或其药物可接受的盐，以及使用这些化合物治疗高血压的方法。
• Internally Masked Neopentyl Sulfonyl Ester Cyclization Release Prodrugs of Acamprosate, Compositions Thereof, and Methods of Use
  申请人：Li Yunxiao

  公开号：US20090099253A1

  公开（公告）日：2009-04-16

  Internally masked neopentyl sulfonyl ester prodrugs of acamprosate, pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs exhibiting enhanced oral bioavailability and methods of using acamprosate prodrugs to treat neurodegenerative disorders, psychotic disorders, mood disorders, anxiety disorders, somatoform disorders, movement disorders, substance abuse disorders, binge eating disorder, cortical spreading depression related disorders, tinnitus, sleeping disorders, multiple sclerosis, and pain are disclosed.

  内部掩盖的新戊基磺酰酯前药，包含这种前药的药物组合物，以及使用这种前药和组合物治疗疾病的方法被披露。具体来说，披露了展现增强口服生物利用度的阿卡姆普罗酸前药以及使用阿卡姆普罗酸前药治疗神经退行性疾病、精神障碍、情绪障碍、焦虑障碍、躯体形式障碍、运动障碍、物质滥用障碍、暴饮暴食障碍、皮层扩散性抑郁相关障碍、耳鸣、睡眠障碍、多发性硬化症和疼痛的方法。
• A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
  作者：Sami Tlais、Ronald Clark、Gregory Dudley

  DOI：10.3390/molecules14125216

  日期：——

  four-step, asymmetric synthesis of a chiral propargyl alcohol 1 from (R)-pantolactone is described. A key feature of the synthesis is a diastereoselective acetylide addition to a chiral alpha-alkoxy-aldehyde 7, in which unusual Felkin selectivity is observed, despite the potential for chelation control. Crystalline propargyl alcohol 1 is valuable for complex molecule synthesis, and is easy to prepare

  描述了从 (R)-泛内酯合成手性炔丙醇 1 的四步不对称合成。该合成的一个关键特征是非对映选择性乙炔化物添加到手性 α-烷氧基醛 7 中，尽管具有螯合控制的潜力，但仍观察到了不寻常的 Felkin 选择性。结晶炔丙醇 1 对于复杂分子的合成很有价值，并且易于制备多克数量和高非对映体纯度。
• A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals
  作者：Sami F Tlais、Gregory B Dudley

  DOI：10.3762/bjoc.7.66

  日期：——

  A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catalysis in the activation of alkyne π-systems.

  一种高效合成含氧5,5-螺环缩酮的方法被用于头孢菌素类化合物的合成。在甲醇中，氯化金(I)诱导了一种受保护的炔三醇的环异构化反应，并伴随去保护作用，形成了一种具有战略性羟基化的5,5-螺环缩酮，尽管可能存在区域化学复杂性和生成呋喃的可能性。其他晚期过渡金属Lewis酸的效果较差。甲醇作为溶剂有助于抑制不良呋喃副产物的生成。这项研究提供了另一个金催化在激活炔π-体系中的优势的例子。
• An Effective Method for the Preparation of Optically Active Polyoxy 8-Membered Ring Enone Corresponding to the B Ring of Taxol
  作者：Isamu Shiina、Jun Shibata、Yumiko Imai、Ryoutarou Ibuka、Hidehiko Fujisawa、Iwao Hachiya、Teruaki Mukaiyama

  DOI：10.1246/cl.1999.1145

  日期：1999.11

  An effective method for the preparation of 8-membered ring enone 1 in sufficient quantities was developed. First, optically active trialkoxyaldehyde 3 was prepared by diastereoselective dihydroxylation of olefin 7 derived from D-pantolactone. Secondly, 8-chloro-7-oxoaldehydes 20α,β were newly synthesized by the following reactions: namely, MgBr2·OEt2-mediated diastereoselective aldol reaction of the

  开发了一种制备足量8元环烯酮1的有效方法。首先，通过衍生自 D-泛内酯的烯烃 7 的非对映选择性二羟基化制备光学活性三烷氧基醛 3。其次，通过以下反应新合成了 8-氯-7-氧醛 20α,β：即，MgBr2·OEt2 介导的醛 3 与乙烯酮（三甲基甲硅烷基）缩醛 15 的非对映选择性羟醛反应，酯的直接 1,1-二氯乙基化17 与 1,1-二氯乙基锂，所得 α,α-二氯乙基酮 18 与 nBu3SnH 部分脱卤。最后，手性 8-氯-7-氧醛 20α,β 通过 SmI2 介导的羟醛环化作用转化为 8 元环烯酮 1。