4-戊烯-1,3-二醇,4-甲基-,(S)- | 138602-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-戊烯-1,3-二醇,4-甲基-,(S)-
• 英文名称: (S)-4-Methyl-pent-4-ene-1,3-diol
• 英文别名: (S)-2-Methyl-1-pentene-3,5-diol；(3S)-4-methylpent-4-ene-1,3-diol
• CAS: 138602-98-9
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: BZQZWOYZOVQJLT-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-戊烯-1,3-二醇,4-甲基-,(S)- 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以80%的产率得到(S)-4-methyl-pentane-1,3-diol
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019
• 作为产物：
  描述：

  2-methyl-3,5-bis(trimethylsiloxy)pentene 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-戊烯-1,3-二醇,4-甲基-,(S)-
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019

文献信息

• RAFAMYCIN ANALOGS AND METHODS FOR MAKING SAME
  申请人：HANGZHOU ZYLOX PHARMA CO., LTD

  公开号：US20150051242A1

  公开（公告）日：2015-02-19

  A semi-synthetic rapamycin analog with a triazole moiety or a pharmaceutically acceptable salt or prodrug thereof, is a broad-spectrum cytostatic agent and a mTOR inhibitor, and is useful in the treatment of various cancers, or tumors in organs such as kidney, liver, breast, head and neck, lung, prostate, and restenosis in coronary arteries, peripheral arteries, and arteries in the brain, immune and autoimmune diseases. Also disclosed are fungal growth-, restenosis-, post-transplant tissue rejection- and immune- and autoimmune disease-inhibiting compositions and a method of inhibiting cancer, fungal growth, restenosois, post-transplant tissue rejection, and immune and autoimmune disease in a mammal. One particular preferred application of such triazole-moiety containing rapamycin analog is in treating renal carcinoma, lung cancer, colon cancer, and breast cancers wherein potency of the drug, its half-life, tissue distribution properties, and its pharmacokinetic properties including bioavailability through oral and intravenous routes are essential to the clinical outcomes.

  一种含有三唑基团或其药用可接受盐或前药的半合成雷帕霉素类似物，是一种广谱细胞静止剂和 mTOR 抑制剂，可用于治疗各种癌症或器官肿瘤，如肾脏、肝脏、乳腺、头颈部、肺部、前列腺，以及冠状动脉、外周动脉和脑动脉的再狭窄，免疫和自身免疫疾病。还公开了抑制真菌生长、再狭窄、移植后组织排斥以及免疫和自身免疫疾病的组合物和在哺乳动物中抑制癌症、真菌生长、再狭窄、移植后组织排斥以及免疫和自身免疫疾病的方法。其中一种特定的首选应用是含有三唑基团的雷帕霉素类似物在治疗肾癌、肺癌、结肠癌和乳腺癌方面，药物的效力、半衰期、组织分布特性以及其药代动力学特性，包括口服和静脉途径的生物利用度对临床结果至关重要。
• Salts of a phosphonic acid based prodrug of PMEA
  申请人：Metabasis Therapeutics, Inc.

  公开号：EP2223927B1

  公开（公告）日：2014-10-15
• Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols
  作者：Toshiro Harada、Hideaki Kurokawa、Yasuhiro Kagamihara、Sachi Tanaka、Atsushi Inoue、Akira Oku

  DOI：10.1021/jo00031a019

  日期：1992.2

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.