(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane | 94426-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: 1,3-Dioxolane, 2,2-dimethyl-4-[2-(phenylmethoxy)ethyl]-；2,2-dimethyl-4-(2-phenylmethoxyethyl)-1,3-dioxolane
• CAS: 94426-71-8
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: PQMIOFVDDSZEEA-UHFFFAOYSA-N

物化性质

• 沸点：
  305.5±22.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 在 吡啶 、 sodium hydroxide 、 sodium hydride 、 溶剂黄146 、 甲基磺酰氯 作用下， 反应 68.33h， 生成 1-<4-(benzyloxy)-2-hydroxybutyl>uracil
  参考文献：
  名称：

  Synthesis of 9-(4-hydroxy-2-oxobutyl)guanine, 9-(2,4-dihydroxybutyl)guanine and related acyclic nucleoside analogs

  摘要：

  DOI：

  10.1021/jo00206a005
• 作为产物：
  描述：

  1,2,4-丁三醇 、 氯化苄 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以86%的产率得到(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of diether-linked cationic lipids for gene delivery

  摘要：

  Quaternary ammonium lipids 1b-d, with diether linkages between hydrocarbon chains and butane or hexane backbone, were synthesized for cationic liposome-mediated gene delivery. The synthetic strategy of using C-4 or C-6 synthon permits the achievement of the variation of the hydrophobic domain as well as changes of space between the quaternary ammonium head and the hydrophobic domain in the diether-linked cationic lipids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00187-0

文献信息

• [EN] MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] INHIBITEURS DE MÉTALLOPROTÉINASE MATRICIELLE
  申请人：RANBAXY LAB LTD

  公开号：WO2012038944A1

  公开（公告）日：2012-03-29

  The present invention relates to methyl sulfonamides and N-formamides derivatives of formula (I) and to processes for their syntheses. The invention also relates to pharmacological compositions containing these derivatives and methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatie arthritis, psoriasis, pulmonary fibrosis, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, dry eye, neointimal proliferation which leads to restenosis and ischemic heart failure, stroke, renal disease, tumor metastasis, and other inflammatory disorders characterized by over expression and over activation of an matrix metalloproteinase using the compounds.

  本发明涉及公式（I）的甲基磺酰胺和N-甲酰胺衍生物，以及它们的合成方法。该发明还涉及含有这些衍生物的药物组合物，以及治疗哮喘、类风湿关节炎、慢性阻塞性肺病、鼻炎、骨关节炎、银屑病性关节炎、牛皮癣、肺纤维化、肺部炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、干眼症、新生内膜增生导致再狭窄和缺血性心力衰竭、中风、肾脏疾病、肿瘤转移以及其他以基质金属蛋白酶过度表达和过度活化为特征的炎症性疾病的方法，使用这些化合物。
• Role of Hydroxymethyl Group as a New Hydrophilic 4'-Pocket in 5'-Norcarbocyclic Nucleoside Analogues
  作者：Lian Jin Liu、Joon-Hee Hong

  DOI：10.5012/bkcs.2011.32.2.411

  日期：2011.2.20

  Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-group with antiviral enhancement, novel 4'-hydroxymethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were designed and synthesized from 2,2-dimethyl-1,3-dioxolane-4-ethanol (5) using reiterative Grignard addition and ring-closing metathesis (RCM) as key reactions. The synthesized adenosine phosphonic acids analogues (22) and (23) were subjected to antiviral screening against HIV-1. Compound (23) exhibited moderate anti-HIV activity ($EC_50$ = 8.61 $\mu}M$) in the CEM cell line.

  4'-取代基的空间和电子参数在引导核苷类似物的构象方面发挥着重要作用。为研究4'-基团与抗病毒增强之间的关系，设计并合成了新的4'-羟甲基-5'-诺卡巴环腺苷磷酸类类似物，这些化合物是通过对2,2-二甲基-1,3-二噁烷-4-醇（5）进行重迭格林纳反应和环闭杂交（RCM）为关键反应而得到的。合成的腺苷磷酸类类似物（22）和（23）进行了抗HIV-1的筛选。化合物（23）在CEM细胞系中表现出中等的抗HIV活性（$EC_50$ = 8.61 $\mu}M$）。
• Condensation of 1,2,4-Butanetriol with Carbonyl Compounds and Reactions of Hydroxyalkyl-1,3-dioxacyclanes
  作者：G. Z. Raskil’dina、Yu. G. Borisova、S. S. Zlotskii

  DOI：10.1134/s107036321808008x

  日期：2018.8

  3-dioxolan-4-yl)ethanol and 1,3-dioxan-4-ylmethanol was prepared by reaction of 1,2,4-butanetriol with paraformaldehyde. This mixture was subjected to O-alkylation, O-acylation, condensation with phenyl isocyanate, and substitution of OH groups for Cl. The relative activity of acetone derivatives of glycerol and 1,2,4-butanetriol in reactions with allyl chloride and benzyl chloride was estimated.

  通过使1,2,4-丁三醇与低聚甲醛反应制备2-（1,3-二氧杂戊-4-基）乙醇和1,3-二氧杂-4-基甲醇的异构体的混合物。对该混合物进行O-烷基化，O-酰化，与异氰酸苯酯缩合，以及用OH基团取代Cl。估计了甘油和1,2,4-丁三醇的丙酮衍生物在与烯丙基氯和苄基氯反应中的相对活性。
• A Convenient Synthesis of 6-Hydroxy-7,9-bis(<i>p</i>-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione
  作者：Masanori Yamaura、Tsuneji Suzuki、Hironobu Hashimoto、Juji Yoshimura、Chung-gi Shin

  DOI：10.1246/bcsj.58.2812

  日期：1985.10

  The title compound, the key intermediate for a total synthesis of bicyclomycin, was synthesized from N,N′-diacetyl anhydroglycine through twelve steps. The three-carbon branch for the construction of the bicyclic skeleton was introduced to the 2,5-piperazinedione ring as an alkylidene substituent, and then the olefinic function was converted into a diol function. The formation of bicyclic ring was achieved by treatment with N-bromosuccinimide followed by the intramoleculer substitution of the primary hydroxyl group in the side chain, and finally the secondary hydroxyl group was converted to the methylene function by an improved Peterson reaction.

  标题化合物是全合成双环霉素的关键中间体，由 N,N′-二乙酰基脱水甘氨酸经过 12 个步骤合成而成。在 2,5-哌嗪二酮环上引入了用于构建双环骨架的三碳分支作为亚烷基取代基，然后将烯烃官能团转化为二醇官能团。双环的形成是通过 N-溴代丁二酰亚胺处理后，侧链中的一级羟基被分子内取代，最后二级羟基通过改进的 Peterson 反应转化为亚甲基官能团。
• Process for preparing butanetriol derivative
  申请人：Daiso Co., Ltd.

  公开号：US20040024261A1

  公开（公告）日：2004-02-05

  A process for preparing a butanetriol derivative of the formula (1) useful as intermediates of medicines 1 wherein R 1 is the same defined below, which comprises reacting a compound of the formula (3) 2 wherein R 1 and R 2 are the different protecting groups, and an ethylene glycol derivative in a basic condition to prepare a compound of the formula (4) or (4 a ) 3 wherein R 1 and R 2 are the same defined above, and then subjecting the compound (4) or (4 a ) to selective deprotection reaction.

  一种制备用于药物中间体的丁三醇衍生物的工艺，其化学式为（1），其中R1如下定义，包括将化合物的反应（3）与乙二醇衍生物在碱性条件下反应，制备化合物（4）或（4a），其中R1和R2是不同的保护基团，并随后对化合物（4）或（4a）进行选择性去保护反应。