6-烯丙基-2,3-二氢-1,4-苯并二氧杂环己烷 | 58169-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 6-烯丙基-2,3-二氢-1,4-苯并二氧杂环己烷
• 英文名称: 6-allyl-1,4-benzodioxane
• 英文别名: 3-[(3,4-Ethylenedioxy)phenyl]-1-propene；6-prop-2-enyl-2,3-dihydro-1,4-benzodioxine
• CAS: 58169-24-7
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: QMWOTQUTMIYGBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-烯丙基儿茶酚	4-allylpyrocatechol	1126-61-0	C9H10O2	150.177

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6-cyclopropylmethyl-1,4-benzodioxane	351342-85-3	C12H14O2	190.242
  ——	6-(2,2-dichlorocyclopropylmethyl)-1,4-benzodioxane	351342-86-4	C12H12Cl2O2	259.132

反应信息

• 作为反应物：
  描述：

  6-烯丙基-2,3-二氢-1,4-苯并二氧杂环己烷 在 dinitrogen tetraoxide 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到6-allyl-7-nitro-1,4-benzodioxane
  参考文献：
  名称：

  与四氧化二氮反应的环丙基和烯丙基取代的芳烃。底物氧化电位对反应方向的影响

  摘要：

  A correlation was found between oxidation potentials of acylcyclopropanes in solution (in CH2Cl2 and CH3CN) and their HOMO energies calculated by semiempirical (AM1) and nonempirical (HF/6-31G and HF/6-31G**) methods. The correlation provides a possibility to forecast the reaction direction of the mentioned substrates and N2O4. The correlation possesses a general character. It was established for instance that arylcyclopropanes, cyclopropylmethyl- and allylbenzenes oxidized at more positive potentials than reduction potential of NO+ and having more positive epsilon(HOMO) than -9.0 eV (AM1), -8.4 eV (HF/6-31G), and -8.3 eV (HF/6-31 G**) reacted with N2O4 following the mechanism "electron transfer - radical pair recombination" affording nitroaromatic derivatives retaining the cyclopropane (or allyl) fragments. Substrates of the same type where the electron transfer to NO+ should be endothermic process and whose HOMO values are less than the above critical numbers react with N2O4 by the mechanism of electrophilic cyclopropane ring opening (with aryl and benzylcyclopropanes) or by electrophilic addition across the double C=C bond (with allylbenzenes).

  DOI：

  10.1023/b:rujo.0000045888.43245.d7
• 作为产物：
  描述：

  3-溴丙烯 、 6-溴-1,4-苯并恶烷 在 magnesium 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以53%的产率得到6-烯丙基-2,3-二氢-1,4-苯并二氧杂环己烷
  参考文献：
  名称：

  与四氧化二氮反应的环丙基和烯丙基取代的芳烃。底物氧化电位对反应方向的影响

  摘要：

  A correlation was found between oxidation potentials of acylcyclopropanes in solution (in CH2Cl2 and CH3CN) and their HOMO energies calculated by semiempirical (AM1) and nonempirical (HF/6-31G and HF/6-31G**) methods. The correlation provides a possibility to forecast the reaction direction of the mentioned substrates and N2O4. The correlation possesses a general character. It was established for instance that arylcyclopropanes, cyclopropylmethyl- and allylbenzenes oxidized at more positive potentials than reduction potential of NO+ and having more positive epsilon(HOMO) than -9.0 eV (AM1), -8.4 eV (HF/6-31G), and -8.3 eV (HF/6-31 G**) reacted with N2O4 following the mechanism "electron transfer - radical pair recombination" affording nitroaromatic derivatives retaining the cyclopropane (or allyl) fragments. Substrates of the same type where the electron transfer to NO+ should be endothermic process and whose HOMO values are less than the above critical numbers react with N2O4 by the mechanism of electrophilic cyclopropane ring opening (with aryl and benzylcyclopropanes) or by electrophilic addition across the double C=C bond (with allylbenzenes).

  DOI：

  10.1023/b:rujo.0000045888.43245.d7

文献信息

• Bimetallic Palladium/Cobalt Catalysis for Enantioselective Allylic C−H Alkylation via a Transient Chiral Nucleophile Strategy
  作者：Hongkai Wang、Yang Xu、Fangqing Zhang、Yangbin Liu、Xiaoming Feng

  DOI：10.1002/anie.202115715

  日期：2022.3.14

  An asymmetric allylic C−H functionalization has been developed by making use of transient chiral nucleophiles, as well as bimetallic synergistic catalysis with an achiral Pd0 catalyst and a chiral N,N′-dioxide-CoII complex. The corresponding allylated products could be obtained in moderate to good yields with excellent regio- (l/b>20 : 1) and enantioselectivities (up to 99 % ee) under mild reaction

  通过使用瞬态手性亲核试剂以及与非手性 Pd 0催化剂和手性N , N'-二氧化物-Co II配合物的双金属协同催化，已经开发了不对称的烯丙基 C-H 官能化。在温和的反应条件下，可以以中等至良好的收率获得相应的烯丙基化产物，并具有优异的区域选择性（ l/b >20:1）和对映选择性（高达 99% ee ）。
• Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0637580A1

  公开（公告）日：1995-02-08

  A 1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent. The phenylalkene derivative is prepared by reacting an alkenyl halide with metal magnesium to form a Grignard reagent, and then reacting the Grignard reagent with a benzyl halide derivative. An allyl Grignard reagent is prepared by reacting continuously an allyl halide derivative with metal magnesium in an organic solvent, in which the allyl halide derivative and metal magnesium are continuously added to the reaction system and the allyl Grignard reagent formed is continuously removed from the reaction system. The processes provide the intended compounds in high yields, high selectivities and high purities.

  1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent.苯基烷烃衍生物的制备方法是先使烯基卤化物与金属镁反应生成格氏试剂，然后使格氏试剂与苄基卤化物衍生物反应。烯丙基格氏试剂是通过烯丙基卤化物衍生物与金属镁在有机溶剂中连续反应制备的，其中烯丙基卤化物衍生物和金属镁被连续加入反应体系，形成的烯丙基格氏试剂被连续从反应体系中移除。这些工艺可提供高产率、高选择性和高纯度的预期化合物。
• [EN] COMPOUNDS INHIBITING TDG ACTIVITY<br/>[FR] COMPOSÉS INHIBANT L'ACTIVITÉ DE TDG<br/>[ZH] 抑制TDG活性的化合物
  申请人：EPITAS BIOSCIENCES SHANGHAI CO LTD

  公开号：WO2020224396A1

  公开（公告）日：2020-11-12

  本发明提供了一类抑制TDG活性的化合物。具体地，本发明提供了一种如式I所示的具有新颖结构的化合物。本发明的小分子抑制剂对TDG具有优异的抑制作用。
• FUJITA HARUSHIGE; YAMASHITA MASATARO, YUKI GOSEI KAGAKU KYOKAI SHI, J. SOC. ORG. SYN. CHEM., TOKYO <YGKK-AE>, 1+
  作者：FUJITA HARUSHIGE、 YAMASHITA MASATARO

  DOI：——

  日期：——
• Novel Azaindole Inhibitors of Mtp and Apob
  申请人：Guevel Alyx Caroline

  公开号：US20090036481A1

  公开（公告）日：2009-02-05

  The present invention relates to 7-azaindole-based compounds, to processes for the preparation thereof, to pharmaceutical compositions comprising them, and to the use thereof in the preparation of medicaments that are useful as inhibitors of MTP and of ApoB secretion.