4-(2-甲基-1,3-二氧戊环-2-基)-1-丁醇 | 5745-75-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-(2-甲基-1,3-二氧戊环-2-基)-1-丁醇
• 英文名称: 2-methyl-1,3-dioxolane-2-butanol
• 英文别名: 4-(2-methyl-1,3-dioxolan-2-yl)butan-1-ol；1,3-Dioxolane-2-butanol, 2-methyl-
• CAS: 5745-75-5
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: LGRQYAIQTHIDNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-甲基-1,3-二氧戊环-2-基)-1-丁醇 在 吡啶 、 盐酸 、 甲醇 、 potassium carbonate 作用下， 反应 19.0h， 生成 洛米茶碱
  参考文献：
  名称：

  Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues

  摘要：

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.

  DOI：

  10.1021/jm980469t
• 作为产物：
  描述：

  5-已烯-2-酮 在 硼烷四氢呋喃络合物 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 4-(2-甲基-1,3-二氧戊环-2-基)-1-丁醇
  参考文献：
  名称：

  SCH 351448单体单元的立体选择性合成

  摘要：

  大二内酯 SCH 351448 的单体单元由三个结构单元合成。在 C21-C22（Wittig）和 C10-C11（立体选择性醛醇）之间选择了战略断开。两个 2,6-二取代四氢吡喃环的顺式构型是通过立体选择性阳离子还原建立的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600106

文献信息

• Allylic C−H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover
  作者：Alison N. Campbell、Paul B. White、Ilia A. Guzei、Shannon S. Stahl

  DOI：10.1021/ja105829t

  日期：2010.11.3

  Pd-catalyzed C-H oxidation reactions often require the use of oxidants other than O(2). Here we demonstrate a ligand-based strategy to replace benzoquinone with O(2) as the stoichiometric oxidant in Pd-catalyzed allylic C-H acetoxylation. Use of 4,5-diazafluorenone (1) as an ancillary ligand for Pd(OAc)(2) enables terminal alkenes to be converted to linear allylic acetoxylation products in good yields

  Pd 催化的 CH 氧化反应通常需要使用 O(2) 以外的氧化剂。在这里，我们展示了一种基于配体的策略，在 Pd 催化的烯丙基 CH 乙酰氧基化中用 O(2) 作为化学计量氧化剂替换苯醌。使用 4,5-二氮杂芴酮 (1) 作为 Pd(OAc)(2) 的辅助配体可使末端烯烃在 1 atm O(2) 下以良好的产率和选择性转化为线性烯丙基乙酰氧基化产物。机理研究表明，1 促进了 π-烯丙基-Pd(II) 中间体的 CO 还原消除，从而消除了这一关键催化步骤中对苯醌的需求。
• Catalytic asymmetric intramolecular cyclopropanation of enol silyl ether. Synthesis of the phorbol CD-ring skeleton
  作者：Ryosuke Tokunoh、Hiroshi Tomiyama、Mikiko Sodeoka、Masakatsu Shibasaki

  DOI：10.1016/0040-4039(96)00315-2

  日期：1996.4

  The optically active phorbol CD-ring skeleton was constructed using the catalytic asymmetric intramolecular cyclopropanation of enol silyl ether as a key step. Up to 92% ee was achieved using a newly modified bisoxazoline ligand.

  使用烯醇甲硅烷基醚的催化不对称分子内环丙烷化作为关键步骤，构建了旋光性佛波醇CD环骨架。使用新修饰的双恶唑啉配体可实现高达92％的ee。
• δ-Selective Functionalization of Alkanols Enabled by Visible-Light-Induced Ligand-to-Metal Charge Transfer
  作者：Anhua Hu、Jing-Jing Guo、Hui Pan、Haoming Tang、Zhaobo Gao、Zhiwei Zuo

  DOI：10.1021/jacs.7b13131

  日期：2018.2.7

  We demonstrate the application of ligand-to-metal charge transfer (LMCT) excitation to the direct catalytic generation of energetically challenging alkoxy radicals from alcohols through a coordination-LMCT-homolysis process with an abundant and inexpensive cerium salt as the catalyst. This catalytic manifold provides a simple and efficient way to utilize the characteristic reactivity and selectivity

  我们展示了配体到金属电荷转移 (LMCT) 激发的应用，通过配位-LMCT-均裂过程，以丰富且廉价的铈盐作为催化剂，从醇中直接催化生成具有挑战性的烷氧基自由基。这种催化歧管提供了一种简单有效的方法来利用瞬态烷氧基自由基的特征反应性和选择性进行 δ 选择性 CH 键官能化。在不需要预官能化的温和氧化还原中性条件下，该方法提供了一个通用平台，可以从简单而丰富的醇中获取分子复杂性。
• METHODS OF NEUROPROTECTION USING NEUROPROTECTIVE STEROIDS AND A VITAMIN D
  申请人：Stein Donald G.

  公开号：US20110306579A1

  公开（公告）日：2011-12-15

  Described herein are compositions and methods for treating or preventing nervous system injury. In particular, the methods and compositions relate to the use of at least one neuroprotective steroid, such as progesterone, and vitamin D.

  本文描述了用于治疗或预防神经系统损伤的组合物和方法。具体而言，这些方法和组合物涉及使用至少一种神经保护类固醇，如孕激素，和维生素D。
• STEROID ANALOGUES FOR NEUROPROTECTION
  申请人：Macnevin Christopher

  公开号：US20110263553A1

  公开（公告）日：2011-10-27

  Provided are steroid analogues functionalized with polar substituents at the C3 and/or C20 positions of the steroid ring system that exhibit improved water solubility. Also provided are pharmaceutical compositions comprising the steroid analogues and methods using the novel steroid analogues for the treatment and prevention of neurodegeneration in a patient following injury to the central nervous system.

  提供的是具有带极性取代基的类固醇类似物，这些取代基位于类固醇环系统的C3和/或C20位置，具有改善的水溶性。还提供了包含这些类固醇类似物的药物组合物，以及使用新型类固醇类似物治疗和预防中枢神经系统损伤后患者的神经退行性疾病的方法。