4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one | 171110-94-4

• 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-benzyloxy)ethyl-1,3-dioxolan-2-one
• 英文别名: 4-(2-Phenylmethoxyethyl)-1,3-dioxolan-2-one
• CAS: 171110-94-4
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: WARFVHSJHDCDPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-(2-Trityloxy-ethyl)-[1,3]dioxolan-2-one
  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
• 作为产物：
  描述：

  (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one
  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

• One-Pot Synthesis of Cyclic Carbonates from Aldehydes, Sulfur Ylide, and CO2
  作者：Arumugam Sudalai、Ravindra Aher、B. Kumar

  DOI：10.1055/s-0033-1340072

  日期：——

  CH2=SMe2), in the presence of CO2 (1 atm) bubbled sequentially under mild conditions, produces cyclic carbonates in preparative yields. Sodium iodide formed in situ promotes the reaction between epoxide as intermediate and CO2 at ambient conditions, thus constituting a powerful metal-free synthesis of organic cyclic carbonates directly from aldehydes.

  在温和条件下连续鼓泡的 CO2 (1 atm) 存在下，用硫叶立德（CH2=SOMe2 或 CH2=SMe2）处理醛，以制备收率生成环状碳酸酯。在环境条件下，原位形成的碘化钠促进了作为中间体的环氧化物与 CO2 之间的反应，从而构成了直接由醛类强有力的无金属有机环状碳酸酯合成。
• Preparation of Optically Active Diol Derivatives by the Enzymatic Hydrolysis of Cyclic Carbonates
  作者：Kazutsugu Matsumoto、Seiji Fuwa、Megumi Shimojo、Hidehiko Kitajima

  DOI：10.1246/bcsj.69.2977

  日期：1996.10

  A simple enzymatic method for the preparation of optically active 1,2- and 1,3-diol derivatives is disclosed. In the screening of enzymes, racemic 4-[(2-benzyloxy)ethyl]-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-(benzyloxy)butane-1,2-diol (2a). The addition of 10% i-Pr2O to the reaction system dramatically improved

  公开了一种用于制备光学活性 1,2- 和 1,3- 二醇衍生物的简单酶促方法。在酶的筛选中，外消旋 4-[(2-benzyloxy)ethyl]-1,3-dioxolan-2-one (1a) 被猪胰腺脂肪酶 (PPL) 对映选择性水解，得到具有旋光活性的 (R)-1a 和(S)-4-(苄氧基)丁烷-1,2-二醇(2a)。向反应体系中加入 10% i-Pr2O 显着提高了反应活性，以 31% 的产率提供了光学纯的 (R)-1a。PPL 还催化了几种具有高对映选择性的五元环状碳酸酯的水解。值得注意的是，取代基碳数的增加反映了对映选择性的急剧增加。另一方面，六元和七元环状碳酸酯的水解也由 PPL 催化。特别是，六元底物的反应以对映选择性进行。该反应提供了光学活性的 1,3-二醇衍生物，其无法通过迄今为止已知的方法直接制备......
• Enzyme-mediated enantioselective hydrolysis of cyclic carbonates
  作者：Kazutsugu Matsumoto、Seiji Fuwa、Hidehiko Kitajima

  DOI：10.1016/0040-4039(95)01300-7

  日期：1995.9

  The enzyme-mediated enantioselective hydrolysis of cyclic carbonates is disclosed. Racemic 4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-benzyloxybutane-1,2-diol (2a). PPL also catalyzed the hydrolysis of seveal five-membered cyclic carbonates with high enatioselectivity.

  公开了酶介导的环状碳酸酯的对映选择性水解。外消旋4-（2-苄氧基）乙基-1,3-二氧戊环-2-酮（1a）被猪胰腺脂肪酶（PPL）对映体水解，得到旋光的（R）-1a和（S）-4-苄氧基丁烷- 1,2-二醇（2a）。PPL还以高对映选择性催化了数个五元环状碳酸酯的水解。
• ONE STEP PROCESS FOR SYNTHESIS OF CYCLIC CARBONATES
  申请人：Council of Scientific & Industrial Research An Indian registered body incorporated under the Registration of Societies Act (Act XXI of 1860)

  公开号：EP2903974A1

  公开（公告）日：2015-08-12
• US8940748B2
  申请人：——

  公开号：US8940748B2

  公开（公告）日：2015-01-27