(E)-crotonaldehyde cyanohydrin ethyl carbonate | 100573-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (E)-crotonaldehyde cyanohydrin ethyl carbonate
• 英文别名: (1-Cyan-2-butenyl)-ethyl-carbonat；[(E)-1-cyanobut-2-enyl] ethyl carbonate
• CAS: 100573-64-6
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: UKVWGGJOHFVBJW-HWKANZROSA-N

物化性质

• 沸点：
  80 °C(Press: 0.6 Torr)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-crotonaldehyde cyanohydrin ethyl carbonate 、 ethyl 2-((tert-butoxycarbonyloxy)methyl)acrylate 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 生成 C₁₄H₁₉NO₅
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.

  DOI：

  10.1021/ol3007716
• 作为产物：
  描述：

  巴豆醛 、 氰基甲酸乙酯 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(E)-crotonaldehyde cyanohydrin ethyl carbonate
  参考文献：
  名称：

  分两步将α，β-不饱和醛转化为γ-叠氮基-α，β-不饱和腈的过程。

  摘要：

  DOI：

  10.1021/jo010101v

文献信息

• Huenig, Siegfried; Reichelt, Helmut, Chemische Berichte, 1986, vol. 119, # 6, p. 1772 - 1800
  作者：Huenig, Siegfried、Reichelt, Helmut

  DOI：——

  日期：——
• Construction of Highly Functional Quaternary Carbon Stereocenters <i>via</i> an Organocatalytic Tandem Cyanation–Allylic Alkylation Reaction
  作者：Zhe Zhuang、Feng Pan、Jian-Guo Fu、Jian-Ming Chen、Wei-Wei Liao

  DOI：10.1021/ol202499g

  日期：2011.12.2

  The first tertiary amine-catalyzed tandem cyanation-allyic alkylation (CAA) reaction of aldehydes, appropriate cyanide sources, and Morita-Baylis-Hillman (MBH) adducts has been developed, which provides a facile access to densely functionalized products containing O-substituted quaternary centers.
• HUNIG S.; REICHELT H., CHEM. BER., 119,(1986) N 6, 1772-1800
  作者：HUNIG S.、 REICHELT H.

  DOI：——

  日期：——
• Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers
  作者：Zhe Zhuang、Jian-Ming Chen、Feng Pan、Wei-Wei Liao

  DOI：10.1021/ol3007716

  日期：2012.5.4

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.
• A Two-Step Procedure for the Conversion of <i>α,β</i>-Unsaturated Aldehydes into <i>γ</i><i>-</i>Azido-<i>α,β</i>-Unsaturated Nitriles¹
  作者：Donald R. Deardorff、Cullen M. Taniguchi、Sanaz A. Tafti、Henry Y. Kim、So Young Choi、Katherine J. Downey、Thanh V. Nguyen

  DOI：10.1021/jo010101v

  日期：2001.10.1