4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane | 167629-45-0

• 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-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane
• 英文别名: 4-[2-[(4-Methoxyphenyl)methoxy]ethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 167629-45-0
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: ZOCZVNZTROSBKL-UHFFFAOYSA-N

物化性质

• 沸点：
  345.7±27.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane 在 吡啶 、 咪唑 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)-butan-2-one
  参考文献：
  名称：

  A Facile and Convergent Synthesis of Sarmentosin

  摘要：

  A concise synthesis of sarmentosin (1) starting from butane-1,2,4-triol-1,2-acetonide is described. This convergent route can also be employed for the preparation of sarmentosin analogues for structure-activity relationship studies.

  DOI：

  10.1081/scc-120023993
• 作为产物：
  描述：

  1-(4-methoxybenzyloxy)-3-butene 在 四氧化锇 、 N-甲基吲哚酮 、 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 生成 4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  印度海草突触藻的新型β-咔啉胍衍生物tiruchanduramine的分离与合成

  摘要：

  一种新颖β咔啉胍生物碱，tiruchanduramine，从印度海鞘的有效α葡萄糖苷酶抑制剂，外消旋形式的分离和合成Synoicum长喙天蛾属已经实现。

  DOI：

  10.1016/j.tetlet.2005.06.060

文献信息

• An Efficient and Selective Method for Hydrolysis of Acetonides
  作者：Xiangshu Xiao、Donglu Bai

  DOI：10.1055/s-2001-12340

  日期：——

  Acetonide was selectively and efficiently cleaved with cerium (III) chloride heptahydrate and oxalic acid in acetonitrile. This method was found to be of good functionalities compatibility with such acid sensitive groups as Tr, PMB, TBDMS, TBDPS, OAc, OBz, OTs, OTf.

  丙酮酸二苯酯在乙腈中与七水合氯化铈（III）和草酸选择性且高效地进行裂解。发现这种方法与对酸敏感的基团如三苯甲基、对甲氧基苄基、叔丁基二甲基硅基、叔丁基二苯基硅基、乙酸酯、苯甲酸酯、对甲苯磺酸酯、三氟甲磺酸酯等具有良好的功能性兼容性。
• Synthesis of aglycon analogues of sarmentosin and Their bioactivity of lymphocyte proliferation
  作者：Hong Zhang、Rui Xu、Zhongliang Hu、Xuchang He、Donglu Bai、Xiaoyu Li、Xiaofeng Wang

  DOI：10.1016/s0960-894x(02)00801-6

  日期：2002.12

  A number of aglycon analogues of sarmentosin were prepared and their bioactivities on the proliferation of T-lymphocytes and B-lymphocytes were assayed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A Facile and Convergent Synthesis of Sarmentosin
  作者：Xu, Rui、Bai, Donglu

  DOI：10.1081/scc-120023993

  日期：2003.9

  A concise synthesis of sarmentosin (1) starting from butane-1,2,4-triol-1,2-acetonide is described. This convergent route can also be employed for the preparation of sarmentosin analogues for structure-activity relationship studies.
• Terminal Fluoroolefins. The Synthesis of Novel Carboacyclic Nucleosides
  作者：Shawn C. Miller、James R. McCarthy、Jeffrey S. Sabol

  DOI：10.1080/07328319808004223

  日期：1998.6

  A facile preparation of ketone 7 from butanetriol acetonide 5 is reported, and its utility for the synthesis of novel carboacyclic nucleosides 3E, 3Z, 4E and 4Z by the selective manipulation of multiple functionalities is demonstrated.
• Synthesis of Unsaturated Carboacyclic Nucleoside Analogues via Mitsunobu Reactions
  作者：Jinfa Du、Guangyi Wang

  DOI：10.1080/15257770008033028

  日期：2000.5

  2-Substituted allyl alcohols 9 and 14 were prepared starting from butane-1,2,4-triol and glycerol, respectively. Mitsunobu condensations of 9 and 14 with purine and pyrimidine bases, followed by deprotection, afforded a number of acyclonucleosides having 4-hydroxy-2-methylenebutyl or 3,3-bis(hydroxymethyl)-2-methylenepropyl chain.