Pent-4-en-2-yl carbonochloridate | 137128-39-3

• 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: Pent-4-en-2-yl carbonochloridate
• CAS: 137128-39-3
• 化学式: C₆H₉ClO₂
• 分子量: 148.589
• InChiKey: YMQOZYTZNYIDLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Pent-4-en-2-yl carbonochloridate 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 trans-2,4-dimethyl-γ-butyrolactone
  参考文献：
  名称：

  Bachi, Mario D.; Bosch, Eric, Heterocycles, 1989, vol. 28, # 2, p. 579 - 582

  摘要：

  DOI：
• 作为产物：
  描述：

  光气 、 4-戊烯-2-醇 在 三乙胺 作用下， 以 苯 为溶剂， 生成 Pent-4-en-2-yl carbonochloridate
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030

文献信息

• Bachi, Mario D.; Bosch, Eric, Heterocycles, 1989, vol. 28, # 2, p. 579 - 582
  作者：Bachi, Mario D.、Bosch, Eric

  DOI：——

  日期：——
• Diastereoselective intramolecular diels-alder reaction of N-alkoxycarbonyl -1-aza-1,3-butadienes and a total synthesis of the piperidine alkaloid, (±)-sedridine.
  作者：Tadao Uyehara、Naoki Chiba、Ichiro Suzuki、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(00)92173-7

  日期：1991.1

  Total synthesis of (+/-)-sedridine, the piperidine alkaloid, was accomplished on the basis of diastereoselective intramolecular Diels-Alder reaction of the psi',omega'-unsaturated N-alkoxycarbonyl-1-aza-1,3-butadiene generated in situ from N-trimethylsilyl-1-aza-butadiene and the chloroformate of 4-penten-2-ol.
• NOGUTI, XIROSI;ISIKURI, YUKIO;KATO, TOSIRO;YAMAMOTO, SIGEHO;TAKAXASI, ATS+
  作者：NOGUTI, XIROSI、ISIKURI, YUKIO、KATO, TOSIRO、YAMAMOTO, SIGEHO、TAKAXASI, ATS+

  DOI：——

  日期：——
• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.