1,1-dimethylethyl (Z)-1-ethyl-3-pentenyl carbonate | 82770-25-0

• 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: 1,1-dimethylethyl (Z)-1-ethyl-3-pentenyl carbonate
• 英文别名: tert-butyl [(Z)-hept-5-en-3-yl] carbonate
• CAS: 82770-25-0
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: KGWKJHAGLQVEOJ-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  7
• 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：

  1,1-dimethylethyl (Z)-1-ethyl-3-pentenyl carbonate 在 碘 作用下， 以 乙腈 为溶剂， 生成 (4R*,6S*,1'S*)-4-(1-iodoethyl)-6-ethyl-1,3-dioxan-2-one 、 (4R*,6R*,1'S*)-4-(1-iodoethyl)-6-ethyl-1,3-dioxan-2-one
  参考文献：
  名称：

  Carbonate extension. A versatile procedure for functionalization of acyclic homoallylic alcohols with moderate stereocontrol

  摘要：

  DOI：

  10.1021/jo00142a002
• 作为产物：
  描述：

  5-庚炔-3-醇 在 Pd-BaSO₄ 正丁基锂 、 氢气 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 1,1-dimethylethyl (Z)-1-ethyl-3-pentenyl 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.
• BARTLETT, P. A.;MEADOWS, J. D.;BROWN, E. G.;MORIMOTO, AKIRA;JERNSTEDT, K.+, J. ORG. CHEM., 1982, 47, N 21, 4013-4018
  作者：BARTLETT, P. A.、MEADOWS, J. D.、BROWN, E. G.、MORIMOTO, AKIRA、JERNSTEDT, K.+

  DOI：——

  日期：——
• Carbonate extension. A versatile procedure for functionalization of acyclic homoallylic alcohols with moderate stereocontrol
  作者：Paul A. Bartlett、James D. Meadows、Edward G. Brown、Akira Morimoto、Karen K. Jernstedt

  DOI：10.1021/jo00142a002

  日期：1982.10
• 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.