2-[2-(2-Phenylethyl)-1,3-dioxolan-2-yl]acetaldehyde | 72134-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-(2-Phenylethyl)-1,3-dioxolan-2-yl]acetaldehyde
• CAS: 72134-60-2
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: RANCJOXBCIQISL-UHFFFAOYSA-N

物化性质

• 沸点：
  335.0±17.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(2-Phenylethyl)-1,3-dioxolan-2-yl]acetaldehyde 在 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-hydroxy-1,7-diphenylheptan-3-one
  参考文献：
  名称：

  Kato, Nobuharu; Hamada, Yasumasa; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 3323 - 3326

  摘要：

  DOI：
• 作为产物：
  描述：

  1-hydroxy-5-phenylpentan-3-one ethylene acetal 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 以88%的产率得到2-[2-(2-Phenylethyl)-1,3-dioxolan-2-yl]acetaldehyde
  参考文献：
  名称：

  Oxaziridine-Mediated Intramolecular Amination of sp³-Hybridized C−H Bonds

  摘要：

  We describe a new oxaziridine-mediated approach to the amination of sp(3)-hybridized C-H bonds. In the presence of a copper(II) catalyst, N-sulfonyl oxaziridines participate in efficient intramolecular cyclization reactions to afford a variety of piperidine and tetrahydroisoquinoline structures. The aminal intermediates provide a convenient functional handle for further elaboration of these structures, demonstrating the utility of this new methodology for the rapid construction of structurally complex nitrogen-containing heterocycles.

  DOI：

  10.1021/ja906183g

文献信息

• Elder, Todd; Gregory, Lynn C.; Orozco, Arminda, Synthetic Communications, 1989, vol. 19, # 5and6, p. 763 - 768
  作者：Elder, Todd、Gregory, Lynn C.、Orozco, Arminda、Pflug, Jodi L.、Wiens, P. Scott、Wilkinson, T. J.

  DOI：——

  日期：——
• Concise Total Syntheses of (+)-Strictifolione and (6<i>R</i>)-6-[(4<i>R</i>,6<i>R</i>)-4,6-Dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2<i>H</i>-pyran-2-one
  作者：Shibing Tang、Xingang Xie、Xiaolei Wang、Liuer He、Ke Xu、Xuegong She

  DOI：10.1021/jo101875w

  日期：2010.12.3

  Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.
• ELDER, TODD;GREGORY, LYNN C.;OROZCO, ARMINDA;PFLUG, JODI L.;WIENS, P. SCO+, SYNTH. COMMUN., 9,(1989) N-6, C. 763-767
  作者：ELDER, TODD、GREGORY, LYNN C.、OROZCO, ARMINDA、PFLUG, JODI L.、WIENS, P. SCO+

  DOI：——

  日期：——
• KATO, NOBUHARU;HAMADA, YASUMASA;SHIOIRI, TAKAYUKI, CHEM. AND PHARM. BULL., 1984, 32, N 8, 3323-3326
  作者：KATO, NOBUHARU、HAMADA, YASUMASA、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——
• Oxaziridine-Mediated Intramolecular Amination of sp³-Hybridized C−H Bonds
  作者：Charles P. Allen、Tamas Benkovics、Amanda K. Turek、Tehshik P. Yoon

  DOI：10.1021/ja906183g

  日期：2009.9.9

  We describe a new oxaziridine-mediated approach to the amination of sp(3)-hybridized C-H bonds. In the presence of a copper(II) catalyst, N-sulfonyl oxaziridines participate in efficient intramolecular cyclization reactions to afford a variety of piperidine and tetrahydroisoquinoline structures. The aminal intermediates provide a convenient functional handle for further elaboration of these structures, demonstrating the utility of this new methodology for the rapid construction of structurally complex nitrogen-containing heterocycles.