2-(hydroxymethyl)-4,4-dimethoxybutan-1-ol | 99776-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxymethyl)-4,4-dimethoxybutan-1-ol
• 英文别名: 2-Hydroxymethyl-4,4-dimethoxybutan-1-ol；4,4-Dimethoxy-2-(hydroxymethyl)butanol；1,3-Propanediol, 2-(2,2-dimethoxyethyl)-；2-(2,2-dimethoxyethyl)propane-1,3-diol
• CAS: 99776-32-6
• 化学式: C₇H₁₆O₄
• 分子量: 164.202
• InChiKey: HZMZQSQAYFTAPH-UHFFFAOYSA-N

物化性质

• 沸点：
  269.1±40.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-4,4-dimethoxybutan-1-ol 在 吡啶 、 pyridin; (+/-)-2-oxo-bornane-10-sulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 4-<<(phenoxycarbonyl)oxy>methyl>-2-methoxytetrahydrofuran
  参考文献：
  名称：

  4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists

  摘要：

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.

  DOI：

  10.1021/jm00082a007
• 作为产物：
  描述：

  diethyl 2-(2,2-dimethoxyethyl)malonate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 2-(hydroxymethyl)-4,4-dimethoxybutan-1-ol
  参考文献：
  名称：

  Rational hopping of a peptidic scaffold into non-peptidic scaffolds: structurally novel potent proteasome inhibitors derived from a natural product, belactosin A

  摘要：

  基于构建的药效团模型，对天然产物belactosin A衍生物进行合理的支架跳跃，最终导致识别出明显简化的高效非肽衍生物。

  DOI：

  10.1039/c3cc48818g

文献信息

• A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine
  作者：Stephen G. Davies、Paul M. Roberts、Peter T. Stephenson、Helen R. Storr、James E. Thomson

  DOI：10.1016/j.tet.2009.07.010

  日期：2009.9

  The total synthesis of (+)-pilocarpine (as its nitrate salt) has been achieved in nine steps and 30% overall yield starting from racemic 2-(2′,2′-dimethoxyethyl)propane-1,3-diol, which was desymmetrised via an enzymatic protocol. A high yielding synthesis of a key α-ethylidene lactone precursor has been developed, which involves the palladium-catalysed decarboxylation/carbonylation of a 1,3-dioxan-2-one

  从外消旋的2-（2'，2'-二甲氧基乙基）丙烷-1,3-二醇开始，分9步完成了（+）-pilocarpine（作为其硝酸盐）的总合成，总收率达30％。通过酶促方案去对称化。已经开发了关键α-亚乙基内酯前体的高产率合成，其涉及钯催化的1，3-二恶烷-2-酮的脱羧/羰基化以形成γ-丁内酯环。随后对α-亚乙基内酯进行氢化，引入C（3）-立体化学，得到（+）-pilocarpine和（+）-isopilocarpine的72:28混合物，可通过（+）-pilocarpine硝酸盐的重结晶轻松分离盐。
• Guanine derivative
  申请人：Astra Lakemedel Aktiebolag

  公开号：US04798833A1

  公开（公告）日：1989-01-17

  Antivirally active compounds of the formula ##STR1## wherein A is ##STR2## wherein m is 1 or 2, n is 1 or 2, whereby m is 1 when n is 2 and m is 2 when n is 1, R.sub.a ' is (CH.sub.2).sub.p OH, NHCONH.sub.2 or COR.sub.a ", R.sub.a " is hydrogen, hydroxy or amino, p is 1 to 4, R.sub.b ' and R.sub.b " are independently selected from hydrogen or (CH.sub.2).sub.p OH, with the proviso that at least one of R.sub.b ' or R.sub.b " is hydrogen; or R.sub.b ' and R.sub.b " together constitute an additional carbon-carbon bond to form an alkyne; or a physiologically acceptable salt, geometric or optical isomer thereof; pharmaceutical preparations containing the compounds and methods for treatment of virus infections.

  该公式代表的抗病毒活性化合物，其中A是，m为1或2，n为1或2，当n为2时m为1，当n为1时m为2，R.sub.a '为(CH.sub.2).sub.p OH，NHCONH.sub.2或COR.sub.a "，R.sub.a "为氢、羟基或氨基，p为1至4，R.sub.b '和R.sub.b "分别选择自氢或(CH.sub.2).sub.p OH，但至少其中一个为氢；或R.sub.b '和R.sub.b "一起构成额外的碳-碳键形成炔烃；或其生理上可接受的盐、几何或光学异构体；含有该化合物的药物制剂和治疗病毒感染的方法。
• Synthesis of ()-2′-oxa-carbocyclic-2′,3′-dideoxynucleosides as potential anti-HIV agents
  作者：Mark J. Bamford、David C. Humber、Richard Storer

  DOI：10.1016/0040-4039(91)80873-5

  日期：1991.1

  Novel 2′,3′-dideoxynucleosides, having the pentofuranosyl oxygen at the 2′-position, were obtained by a short synthetic route from diethyl malonate and bromoacetaldehyde dimethyl acetal. The results of biological testing against HIV-1 in vitro are presented.

  通过丙二酸二乙酯和溴乙醛二甲基乙缩醛的短合成路线获得了在2'-位具有戊呋喃糖基氧的新型2'，3'-二脱氧核苷。介绍了针对HIV-1的体外生物测试结果。
• Derivatives of Guanine, process for their preparation and a pharmaceutical preparation
  申请人：Astra Läkemedel Aktiebolag

  公开号：EP0146516A2

  公开（公告）日：1985-06-26

  Antivirally active compounds of the formula wherein A is or wherein: m is 1 or 2, n is 1 or 2, whereby m is 1 when n is 2 and m is 2 when n is 1, R'a is (CH2)pOH, NHCONH2 or COR"a, R"a is hydrogen, hydroxy or amino, p is 1 to 4, R'b and R" are independently selected from hydrogen or (CH2)pOH, with the proviso that at least one of R'b or R"b is hydrogen; or R'b and R"b together constitute an additional carbon-carbon bond to form an alkyne; or a physiologically acceptable salt, geometric or optical isomer thereof; processes for preparation of said compounds, pharmaceutical preparations containing the compounds, methods for treatment of virus infections and the medical use of the compounds.

  式中A为 或 的抗病毒活性化合物 其中：m为1或2，n为1或2，其中n为2时m为1，n为1时m为2，R'a为(CH2)pOH、NHCONH2或COR "a，R "a为氢、羟基或氨基，p为1至4，R'b和R "独立地选自氢或(CH2)pOH，但R'b或R "b中至少有一个为氢；或R'b和R "b共同构成额外的碳-碳键以形成炔；或其生理上可接受的盐、几何或光学异构体；制备所述化合物的工艺、含有所述化合物的药物制剂、治疗病毒感染的方法以及所述化合物的医疗用途。
• Bailey, Stuart; Harnden, Michael R., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2767 - 2776
  作者：Bailey, Stuart、Harnden, Michael R.

  DOI：——

  日期：——