(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetonitrile | 106134-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetonitrile
• 英文别名: 2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetonitrile；(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetonitrile；2-(1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetonitrile
• CAS: 106134-81-0
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: HVBOUUSMAVZZPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  479.8±40.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  依托度酸 在 吡啶 、 草酰氯 、 三氟乙酸酐 作用下， 生成 (1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetonitrile
  参考文献：
  名称：

  A Novel Substitution Reaction of Tetrahydropyrano[3,4-b]indole Derivative — Chain Extension and Structural Correlation Study

  摘要：

  An unusual cyanation with rearrangement of a 1-chloromethyltetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.

  DOI：

  10.3987/com-02-9703

文献信息

• Synthesis of Oxacyclic Scaffolds via Dual Ruthenium Hydride/Brønsted Acid-Catalyzed Isomerization/Cyclization of Allylic Ethers
  作者：Erhad Ascic、Ragnhild G. Ohm、Rico Petersen、Mette R. Hansen、Casper L. Hansen、Daniel Madsen、David Tanner、Thomas E. Nielsen

  DOI：10.1002/chem.201304270

  日期：2014.3.17

  A ruthenium hydride/Brønsted acid‐catalyzed tandem sequence is reported for the synthesis of 1,3,4,9‐tetrahydropyrano[3,4‐b]indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to enol ethers (Ru catalysis), then to oxocarbenium ions (Brønsted acid catalysis) amenable to endo cyclization

  据报道，氢化钌/布朗斯台德酸催化的串联序列可用于合成1,3,4,9-四氢吡喃[3,4- b ]吲哚（THPIs）和相关的氧环骨架。该过程被设计的前提是容易得到的烯丙基醚将经历连续的异构化，第一至烯醇醚（RU催化），然后到oxocarbenium离子（布朗斯台德酸催化）适合于内 环化栓系亲核体。该方法不仅为合成THPI的传统oxa-Pictet-Spengler反应提供了有吸引力的替代方法，而且还方便地获得THPI同类物和其他重要的乙环（如乙缩醛）。
• A Novel Substitution Reaction of Tetrahydropyrano[3,4-b]indole Derivative — Chain Extension and Structural Correlation Study
  作者：Shan-Yen Chou

  DOI：10.3987/com-02-9703

  日期：——

  An unusual cyanation with rearrangement of a 1-chloromethyltetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.