1-Bromo-2-prop-2-ynoxycyclopentane | 80997-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Bromo-2-prop-2-ynoxycyclopentane
• CAS: 80997-78-0
• 化学式: C₈H₁₁BrO
• 分子量: 203.079
• InChiKey: SQQPFWGVBRZKRC-UHFFFAOYSA-N

物化性质

• 沸点：
  104 °C(Press: 23 Torr)
• 密度：
  1.37±0.1 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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Bromo-2-prop-2-ynoxycyclopentane 在 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 chlorocobaloxime(III) 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 rac-(3aR,6aR)-3-methylenehexahydro-2H-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Reductive cyclization of 2-[(2-propynyl)oxy]ethyl bromides by a cobalt complex, cobaloxime(I). A new method for the synthesis of .alpha.-methylene-.gamma.-butyrolactones

  摘要：

  DOI：

  10.1021/jo00348a040
• 作为产物：
  描述：

  2-丙炔-1-醇 、 环戊烯 在 N-溴代丁二酰亚胺(NBS) 作用下， 反应 1.0h， 以100%的产率得到1-Bromo-2-prop-2-ynoxycyclopentane
  参考文献：
  名称：

  α-亚甲基-γ-丁内酯的前体β-溴丙-2-炔基混合缩醛和溴乙烯双缩二烯丙基混合缩醛的合成新途径

  摘要：

  N-溴代琥珀酰亚胺在甲醇中的β-溴代烯丙基醚（3a - g）或烯丙基烯丙基醚（8d - f）进行卤代反应可得到不饱和卤代化合物（5a - g）或（9d - f），这些化合物通过均相碳环化作用转化为α -亚甲基-γ-丁内酯（7a – g）。

  DOI：

  10.1039/c39880000237

文献信息

• Hiv Protease Inhibitors
  申请人：Ekegren Jenny

  公开号：US20080249102A1

  公开（公告）日：2008-10-09

  Compounds of the formula I: wherein R 1 , R 2 , X and N are as defined in the specification; E is N, CH; A′ and A″ are terminal groups as defined in the specification. The compounds have utility as HIV-1 protease inhibitors.

  化合物的公式I： 其中R1，R2，X和N如规范中定义；E为N，CH；A'和A''为规范中定义的末端基团。 这些化合物具有作为HIV-1蛋白酶抑制剂的实用性。
• 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.
• OKABE, MASAMI;ABE, MASAYOSHI;TADA, MASARU, J. ORG. CHEM., 1982, 47, N 9, 1775-1777
  作者：OKABE, MASAMI、ABE, MASAYOSHI、TADA, MASARU

  DOI：——

  日期：——
• DULCERE, J. P.;MIHOUBI, M. N.;RODRIGUEZ, J., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 3, 237-239
  作者：DULCERE, J. P.、MIHOUBI, M. N.、RODRIGUEZ, J.

  DOI：——

  日期：——
• US7807677B2
  申请人：——

  公开号：US7807677B2

  公开（公告）日：2010-10-05