1,7-dibromo-2-heptyne | 214074-30-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1,7-dibromo-2-heptyne
• 英文别名: 1,7-Dibromohept-2-yne
• CAS: 214074-30-3
• 化学式: C₇H₁₀Br₂
• 分子量: 253.964
• InChiKey: OHUXCMNUQIFJJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,7-dibromo-2-heptyne 在 偶氮二异丁腈 、 camphor-10-sulfonic acid 、 三丁基氯化锡 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Chiral acyl radical equivalents: 5-exo cyclization of conformationally constrained 1,3-dioxolanyl radicals

  摘要：

  Chiral 1,3-dioxolan-2-yl radicals derived from acetals 8 and 9 underwent intramolecular hydrogen abstraction followed by 5-exo-trig cyclization on treatment with tributyltin hydride and AIBN with modest and opposite stereoselectivities. The more highly substituted substrate 13 took part in a similar cascade, triggered by a 5-exo-dig cyclization. In this example the more highly substituted nature of the alkene in the stereocontrolled cyclization resulted in essentially complete diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00633-4
• 作为产物：
  描述：

  2-((7-bromohept-2-yn-1-yl)oxy)tetrahydro-2H-pyran 在 bromotriphenylphosphonium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以74%的产率得到1,7-dibromo-2-heptyne
  参考文献：
  名称：

  Chiral acyl radical equivalents: 5-exo cyclization of conformationally constrained 1,3-dioxolanyl radicals

  摘要：

  Chiral 1,3-dioxolan-2-yl radicals derived from acetals 8 and 9 underwent intramolecular hydrogen abstraction followed by 5-exo-trig cyclization on treatment with tributyltin hydride and AIBN with modest and opposite stereoselectivities. The more highly substituted substrate 13 took part in a similar cascade, triggered by a 5-exo-dig cyclization. In this example the more highly substituted nature of the alkene in the stereocontrolled cyclization resulted in essentially complete diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00633-4

文献信息

• Ogoshi, Sensuke; Stryker, Jeffrey M., Journal of the American Chemical Society, 1998, vol. 120, p. 3514 - 3515
  作者：Ogoshi, Sensuke、Stryker, Jeffrey M.

  DOI：——

  日期：——
• Chiral acyl radical equivalents: 5-exo cyclization of conformationally constrained 1,3-dioxolanyl radicals
  作者：D. Stien、D. Crich、M.P. Bertrand

  DOI：10.1016/s0040-4020(98)00633-4

  日期：1998.9

  Chiral 1,3-dioxolan-2-yl radicals derived from acetals 8 and 9 underwent intramolecular hydrogen abstraction followed by 5-exo-trig cyclization on treatment with tributyltin hydride and AIBN with modest and opposite stereoselectivities. The more highly substituted substrate 13 took part in a similar cascade, triggered by a 5-exo-dig cyclization. In this example the more highly substituted nature of the alkene in the stereocontrolled cyclization resulted in essentially complete diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.