3-(2-bromo-1-ethoxyethoxy)-1-propene | 109603-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-bromo-1-ethoxyethoxy)-1-propene
• 英文别名: 3-(2-bromo-1-ethoxyethoxy)prop-1-ene
• CAS: 109603-98-7
• 化学式: C₇H₁₃BrO₂
• 分子量: 209.083
• InChiKey: MRPKCTRQZKAAGV-UHFFFAOYSA-N

物化性质

• 沸点：
  218.9±25.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  3-(2-bromo-1-ethoxyethoxy)-1-propene 在 三乙胺 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 4-戊烯酸乙酯
  参考文献：
  名称：

  Lidbetter, Paul S.; Marples, Brian A., Synthetic Communications, 1986, vol. 16, # 12, p. 1529 - 1534

  摘要：

  DOI：
• 作为产物：
  描述：

  烯丙醇 、 乙烯基乙醚 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到3-(2-bromo-1-ethoxyethoxy)-1-propene
  参考文献：
  名称：

  乙缩醛中心控制的卤代缩醛的高度立体选择性自由基环化。

  摘要：

  报道了系统的自由基卤缩醛环化（Ueno-Stork反应）的研究，其中缩醛中心是独特的立体生成元素。该高度非对映选择性反应可用于制备多取代的四氢呋喃和γ-内酯。我们在此报告了最多创建三个新手性中心的反应的全部实验细节。为了证明这种方法的潜力，已经实现了与生物活性木脂素相关的（+）-依加醇化物和三环缩醛的短合成。

  DOI：

  10.1002/chem.200390180

文献信息

• Regiospecific and Stereoselective Syntheses of (±)-Reserpine and (−)-Reserpine
  作者：Gilbert Stork、Peng Cho Tang、Michael Casey、Burton Goodman、Masahiro Toyota

  DOI：10.1021/ja055744x

  日期：2005.11.23

  Full details of three approaches to an entirely regio- and stereoselective synthesis of the well-known target reserpine are described, culminating in a total synthesis which efficiently meets these requirements.

  描述了众所周知的目标利血平的完全区域和立体选择性合成的三种方法的全部细节，最终形成有效满足这些要求的全合成。
• Diastereoselective radical cyclization of bromoacetals (Ueno-Stork reaction) controlled by the acetal center
  作者：Félix Villar、Philippe Renaud

  DOI：10.1016/s0040-4039(98)01971-6

  日期：1998.11

  The stereochemistry of the 5-exo-trig cyclization of bromoacetals (Ueno-Stork cyclization) can be controlled from the stereogenic acetal center. High stereoselectivities have been observed for the formation of 4-substituted tetrahydrofurans. Preparation of an optically pure β-substituted γ-butyrolactone by use of an easily removable chiral auxiliary is reported.

  可以从立体缩醛中心控制溴缩醛的5 -exo-trig环化（Ueno-Stork环化）的立体化学。对于形成4-取代的四氢呋喃，已经观察到高的立体选择性。报道了通过使用容易除去的手性助剂制备光学纯的β-取代的γ-丁内酯。
• Igbal, Javed; Srivastava, Rajeev Ranjan; Gupta, Kiran Bala, Synthetic Communications, 1989, vol. 19, # 5and6, p. 901 - 906
  作者：Igbal, Javed、Srivastava, Rajeev Ranjan、Gupta, Kiran Bala、Khan, M. Amin

  DOI：——

  日期：——
• Formation of Some Oxygen-Containing Heterocycles by Radical Cyclization:  The Stereochemical Influence of Anomeric Effects
  作者：Athelstan L. J. Beckwith、Dennis M. Page

  DOI：10.1021/jo980359u

  日期：1998.7.1

  The influence of the anomeric effect on radical cyclization has been examined by determining the stereochemical outcome of the ring closure of 10 suitably substituted radicals. The stereochemistry of the products formed from the acyclic precursors 4a-f indicates that for suitably constituted radicals anomeric interactions stabilize pseudoaxially substituted transition structures 14 thus affording products with stereochemistry the reverse of that normally observed.
• Generation and Mesolysis of PhSeSiR₃]^•-:  Mechanistic Studies by Laser Flash Photolysis and Application for Bimolecular Group Transfer Radical Reactions
  作者：Ganesh Pandey、K. S. Sesha Poleswara Rao、D. K. Palit、J. P. Mittal

  DOI：10.1021/jo972345e

  日期：1998.6.1

  The investigation presented in this paper explores the mechanistic aspects and synthetic potentials of PET promoted reductive activation of selenosilane la to its radical anion la(-.). PET activation of la is achieved through a photosystem comprising a light-absorbing electron-rich aromatic (ERA), such as DMN or DMA, as an electron donor and ascorbic acid as a co-oxidant. The evidence for the ET from excited singlet states of DMN as well as DMA to la is suggested by estimating negative Delta G(et) (-51 and -43.46 kcal mol(-1), respectively) values and nearly diffusion-controlled fluorescence quenching rate constants (k(q)TR) 0.36 x 10(10) M-1 s(-1) and 0.28 x 10(10) M-1 s(-1), respectively, from time-resolved fluorescence quenching study. The transient absorption spectra of DMN.+, DMA(.+), and la(.-) are obtained initially by pulse radiolysis in order to correlate the time-resolved absorption spectral data. Laser flash photolysis studies in the nanosecond time domain have confirmed the generation of la(.-), DMN.+, and DMA(.+), supporting the participation of the triplet state of DMN or DMA in the ET reaction. Mesolytic cleavage of 1a(.-) produced a silyl radical and a phenyl selenide anion. The preparative PET activation of la in acetonitrile in the presence of DMN or DMA leads to the formation of 5 and 6, confirming the fragmentation pattern of la(.-). The overall ET rate constants (K-r(DMN) = 0.99 x 10(10) M-1 s(-1) and k(r)(DMA) = 1.62 x 10(10) M-1 s(-1)) and limiting quantum yields (phi(lim)DMN) = 0.034 and phi(lim)(DMA) = 0.12) are estimated from the inverse plot (1/[la] vs 1/phi(dis)) Obtained by measuring the dependence of photodissociation quantum yields of la at its maximum concentration in the presence of DMN or DMA. Silicon-centered radical species generated from the mesolysis of la(.-) are utilized for initiating a radical reaction by the abstraction of halogen atom from -C-X (X = Cl, Br) bonds, while PhSe- terminates the radical sequences via PhSeSePh. This concept is successfully applied for the bimolecular group transfer (BMGT) radical reactions and intermolecular radical chain addition reactions.