12-bromo-2-dodecanon-ethylenacetal | 118399-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-bromo-2-dodecanon-ethylenacetal
• 英文别名: 12-Brom-2-dodecanon-ethylenacetal；2-(10-Bromodecyl)-2-methyl-1,3-dioxolane
• CAS: 118399-89-6
• 化学式: C₁₄H₂₇BrO₂
• 分子量: 307.271
• InChiKey: ZWBIKIYKIGNFLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-bromo-2-dodecanon-ethylenacetal 在 palladium on activated charcoal 六甲基磷酰三胺 、 barium dihydroxide 、 硫酸 、 氢气 、 magnesium 、 1,2-二溴乙烷 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 21.25h， 生成 12-[(2S,5R,6R)-5-羟基-6-甲基-2-哌啶基]-2-十二烷酮
  参考文献：
  名称：

  Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine

  摘要：

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00537-x
• 作为产物：
  描述：

  12-bromododecan-2-one 、 乙二醇 生成 12-bromo-2-dodecanon-ethylenacetal
  参考文献：
  名称：

  HASSEBERG, HANS-ALBRECHT;GERLACH, HANS, LIEBIGS ANN. CHEM.,(1989) N, C. 255-261

  摘要：

  DOI：

文献信息

• Hasseberg, Hans-Albrecht; Gerlach, Hans, Liebigs Annalen der Chemie, 1989, p. 255 - 262
  作者：Hasseberg, Hans-Albrecht、Gerlach, Hans

  DOI：——

  日期：——
• HASSEBERG, HANS-ALBRECHT;GERLACH, HANS, LIEBIGS ANN. CHEM.,(1989) N, C. 255-261
  作者：HASSEBERG, HANS-ALBRECHT、GERLACH, HANS

  DOI：——

  日期：——
• Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine
  作者：Jörg Oetting、Jens Holzkamp、Hartmut H. Meyer、Axel Pahl

  DOI：10.1016/s0957-4166(96)00537-x

  日期：1997.2

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.