(E)-5-(undec-1-en-1-yl)benzo[d][1,3]dioxole

• 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: (E)-5-(undec-1-en-1-yl)benzo[d][1,3]dioxole
• 英文别名: (E)-5-(undec-1-enyl)benzo[d][1,3]dioxole；5-undec-1-enyl-benzo[1,3]dioxole；5-Undec-1-enyl-benzo[1,3]dioxol；5-[(E)-undec-1-enyl]-1,3-benzodioxole
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: DEHDKPYUMUUMTK-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-(undec-1-en-1-yl)benzo[d][1,3]dioxole 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 水 作用下， 反应 50.5h， 以79%的产率得到6-Nonyl-5H-indeno[5,6-d][1,3]dioxol-5-ol
  参考文献：
  名称：

  Domino synthesis of indenols and alkyl-indene ethers under modified Vilsmeier conditions

  摘要：

  Indenols are produced in high yields through domino reactions, when electron-rich trans-stilbenes and other trans arylalkyl olefins were subjected to Vilsmeier formylation in the presence of excess POCl3 in a one-pot procedure. The method is even suitable for converting aryl-alkyl carbinols (precursors for olefins) directly into indenols. The corresponding indene ethers could be prepared in high yields directly when less reactive alpha,beta-unsaturated aldehydes were subjected to cyclization in alcoholic HCl. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.126
• 作为产物：
  描述：

  1-壬醇 在 咪唑 、 copper acetylacetonate 、 碘 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 (E)-5-(undec-1-en-1-yl)benzo[d][1,3]dioxole 、 5-(undec-1-en-1-yl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  α，β-不饱和酸与烷基碘光诱导的铜促进的区域和立体选择性脱羧烷基化

  摘要：

  报道了第一个UV诱导的，铜催化的α，β-不饱和酸与烷基碘的区域选择性和立体选择性脱羧偶联的例子。在标准条件下，1°，2°和3°烷基碘与获得的E-选择性烯烃平稳地进行，收率均匀且产率高。

  DOI：

  10.1021/acs.orglett.7b03289

文献信息

• Highly <i>E</i>-Selective, Stereoconvergent Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Ethers
  作者：Guo-Ming Ho、Heiko Sommer、Ilan Marek

  DOI：10.1021/acs.orglett.9b00946

  日期：2019.4.19

  An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously substituted styrene derivatives. An olefinic mixture with respect to the alkenyl ethers can be employed, thereby circumventing the stereodefined synthesis of starting materials. Preliminary mechanistic investigations indicate a nickel-catalyzed olefin isomerization following initial stereoretentive cross-coupling.
• Gokhale et al., Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, <hi>1948</hi>, vol. 16/5 A, p. 47,51
  作者：Gokhale et al.

  DOI：——

  日期：——
• Photoinduced, Copper-Promoted Regio- and Stereoselective Decarboxylative Alkylation of α,β-Unsaturated Acids with Alkyl Iodides
  作者：Chao Wang、Yingjie Lei、Mengzhun Guo、Qinyu Shang、Hong Liu、Zhaoqing Xu、Rui Wang

  DOI：10.1021/acs.orglett.7b03289

  日期：2017.12.1

  The first example of UV light-induced, copper-catalyzed regio- and stereoselective decarboxylative coupling of α,β-unsaturated acids with alkyl iodides was reported. Under standard conditions, the 1°, 2°, and 3° alkyl iodides proceeded smoothly with the E-selective alkenes obtained in uniformly good yields and high stereoselectivities.

  报道了第一个UV诱导的，铜催化的α，β-不饱和酸与烷基碘的区域选择性和立体选择性脱羧偶联的例子。在标准条件下，1°，2°和3°烷基碘与获得的E-选择性烯烃平稳地进行，收率均匀且产率高。
• Domino synthesis of indenols and alkyl-indene ethers under modified Vilsmeier conditions
  作者：Parvinder Pal Singh、P. Bhaskar Reddy、Sanghapal D. Sawant、S. Koul、S.C. Taneja、H.M. Sampath Kumar

  DOI：10.1016/j.tetlet.2006.07.126

  日期：2006.10

  Indenols are produced in high yields through domino reactions, when electron-rich trans-stilbenes and other trans arylalkyl olefins were subjected to Vilsmeier formylation in the presence of excess POCl3 in a one-pot procedure. The method is even suitable for converting aryl-alkyl carbinols (precursors for olefins) directly into indenols. The corresponding indene ethers could be prepared in high yields directly when less reactive alpha,beta-unsaturated aldehydes were subjected to cyclization in alcoholic HCl. (c) 2006 Elsevier Ltd. All rights reserved.