Tert-butyl hept-1-en-4-yl carbonate | 145531-95-9

• 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: Tert-butyl hept-1-en-4-yl carbonate
• CAS: 145531-95-9
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: VTFMQCFFDDCOFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  247.7±19.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  Tert-butyl hept-1-en-4-yl carbonate 在 一溴化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (4R,6S)-4-Iodomethyl-6-propyl-[1,3]dioxan-2-one 、 (4S,6S)-4-Iodomethyl-6-propyl-[1,3]dioxan-2-one
  参考文献：
  名称：

  Iodine monobromide (IBr) at low temperature: A superior protocol for diastereoselective cyclizations of homoallylic carbonates

  摘要：

  Iodine monobromide (IBr) induces efficient electrophilic cyclizations of homoallylic t-butyl carbonates in toluene or methylene chloride al low temperature, affording significantly better diastereoselectivity than iodine (I2) in acetonitrile.

  DOI：

  10.1016/s0040-4039(00)79009-5
• 作为产物：
  描述：

  1-庚烯-4-醇 、 2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 在 正丁基锂 作用下， 生成 Tert-butyl hept-1-en-4-yl carbonate
  参考文献：
  名称：

  Iodine monobromide (IBr) at low temperature: enhanced diastereoselectivity in electrophilic cyclizations of homoallylic carbonates

  摘要：

  Iodine monobromide affords superior diastereoselectivity in low-temperature electrophilic cyclizations of homoallylic carbonates. Solvent and temperature effects and the scope and limitations of the method are discussed; optimal selectivity is obtained in toluene at -80 to -85-degrees-C. The latter protocol generally furnishes significantly enhanced selectivity, vis-a-vis the original procedure employing 12 in acetonitrile at -20-degrees-C; for example, the IBr-induced cyclization of 14 affords a 25.8:1 mixture of 15 and 16, whereas I2 gives an 8.4:1 ratio. An equilibration experiment established that the diastereoselectivity derives primarily or exclusively from kinetic control of the cyclization process.

  DOI：

  10.1021/jo00066a024

文献信息

• Iodine monobromide (IBr) at low temperature: A superior protocol for diastereoselective cyclizations of homoallylic carbonates
  作者：James J.-W. Duan、Paul A. Sprengeler、Amos B. Smith

  DOI：10.1016/s0040-4039(00)79009-5

  日期：1992.10

  Iodine monobromide (IBr) induces efficient electrophilic cyclizations of homoallylic t-butyl carbonates in toluene or methylene chloride al low temperature, affording significantly better diastereoselectivity than iodine (I2) in acetonitrile.
• Iodine monobromide (IBr) at low temperature: enhanced diastereoselectivity in electrophilic cyclizations of homoallylic carbonates
  作者：James J. W. Duan、Amos B. Smith

  DOI：10.1021/jo00066a024

  日期：1993.7

  Iodine monobromide affords superior diastereoselectivity in low-temperature electrophilic cyclizations of homoallylic carbonates. Solvent and temperature effects and the scope and limitations of the method are discussed; optimal selectivity is obtained in toluene at -80 to -85-degrees-C. The latter protocol generally furnishes significantly enhanced selectivity, vis-a-vis the original procedure employing 12 in acetonitrile at -20-degrees-C; for example, the IBr-induced cyclization of 14 affords a 25.8:1 mixture of 15 and 16, whereas I2 gives an 8.4:1 ratio. An equilibration experiment established that the diastereoselectivity derives primarily or exclusively from kinetic control of the cyclization process.