5-(1-methoxypropyl)-1,3-benzodioxolane | 73455-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(1-methoxypropyl)-1,3-benzodioxolane
• 英文别名: 5-(1-methoxy-propyl)-benzo[1,3]dioxole；5-(1-Methoxy-propyl)-benzo[1,3]dioxol；1'-Methoxy-2',3'-dihydrosafrole；5-(1-methoxypropyl)-1,3-benzodioxole
• CAS: 73455-03-5
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: PBFANQACQQLPPK-UHFFFAOYSA-N

物化性质

• 沸点：
  251.3±29.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  5-(1-methoxypropyl)-1,3-benzodioxolane 、 水 生成 异黄樟素
  参考文献：
  名称：

  Schimmel & Co., Chemisches Zentralblatt, 1905, vol. 76, # I, p. 1470

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium methylate 作用下， 生成 5-(1-methoxypropyl)-1,3-benzodioxolane
  参考文献：
  名称：

  Schimmel & Co., Chemisches Zentralblatt, 1905, vol. 76, # I, p. 1470

  摘要：

  DOI：

文献信息

• Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation
  作者：Xiaohui Fan、Xiao-Meng Cui、Yong-Hong Guan、Lin-An Fu、Hao Lv、Kun Guo、Hong-Bo Zhu

  DOI：10.1002/ejoc.201301372

  日期：2014.1

  A novel and efficient allylic alkylation reaction between π-activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed C–O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp3–sp3 C–C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds

  通过铁（III）催化的 C-O 醚键断裂，在温和条件下实现了 π 活化醚和烯丙基硅烷之间新型高效的烯丙基烷基化反应。本协议为构建 sp3-sp3 C-C 键提供了一种有吸引力的方法，并且可以通过使用三乙基硅烷作为氢化物转移试剂将苄基和烯丙基醚选择性还原为其相应的碳氢化合物。
• Iron-catalyzed N-alkylation using π-activated ethers as electrophiles
  作者：Xiaohui Fan、Lin-An Fu、Na Li、Hao Lv、Xiao-Meng Cui、Yuan Qi

  DOI：10.1039/c3ob27128e

  日期：——

  A new method for the synthesis of diverse N-alkylation compounds was developed via an iron-catalyzed etheric Csp3–O cleavage with the C–N bond formation in the reaction of π-activated ethers with various nitrogen-based nucleophiles. In addition, the mechanism of this reaction was investigated.

  通过铁催化的醚类Csp3–O键断裂并伴随C–N键形成反应，开发了一种合成多种N-烷基化化合物的新方法，即在π活性醚与各种含氮亲核试剂的反应中生成C–N键。此外，还研究了该反应的机理。
• Efficient assembly of α-aryl and α-vinyl nitriles via iron-catalyzed ether bond activation
  作者：Xiaohui Fan、Kun Guo、Yong-Hong Guan、Lin-An Fu、Xiao-Meng Cui、Hao Lv、Hong-Bo Zhu

  DOI：10.1016/j.tetlet.2013.12.083

  日期：2014.1

  A novel and practical method for the synthesis of diverse alpha-aryl and alpha-vinyl nitriles was developed via an iron-catalyzed sp(3) C-O ether bond cleavage with C-C bond formation in the reaction of pi-activated ethers with TMSCN. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, anti-inflammatory activity and metabolism of alkyl aryl ketones and their derivatives
  作者：V. K. Daukshas、P. G. Gaidyalis、É. B. Udrenaite、L. K. Labanauskas、G. A. Gasperavichene、L. F. Gumbaragite、D. V. Ramanauskas

  DOI：10.1007/bf00764712

  日期：1989.12
• Palladium charcoal-catalyzed deprotection of O-allylphenols
  作者：Miyuki Ishizaki、Makoto Yamada、Shin-ichi Watanabe、Osamu Hoshino、Kiyoshi Nishitani、Maiko Hayashida、Atsuko Tanaka、Hiroshi Hara

  DOI：10.1016/j.tet.2004.05.097

  日期：2004.8

  Allyl aryl ethers can be easily cleaved by the use of 10% Pd/C under mild and basic conditions. The present reaction would involve a SET process rather than a pi-allyl-palladium complex. The scope and limitation of this new deprotective methodology is also described. (C) 2004 Elsevier Ltd. All rights reserved.