(1S,5R,7R)-5,6,6-trimethyl-4-oxatricyclo[5.2.1.01,5]decan-3-one | 292159-47-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,5R,7R)-5,6,6-trimethyl-4-oxatricyclo[5.2.1.01,5]decan-3-one
• CAS: 292159-47-8
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: ZZQDTYAMTADAAS-ZHAHWJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1S,5R,7R)-5,6,6-trimethyl-4-oxatricyclo[5.2.1.01,5]decan-3-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 80.0h， 生成 (1S,2R,4R)-1-[2-(dipropylamino)ethyl]-2,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  衍生自（+）-樟脑和（-）-富琴酮的新型手性1,4-氨基醇，用于将二乙基锌对映体选择性加成到醛中

  摘要：

  从（+）-樟脑和（-）-甲烯酮合成了各种旋光的1,4-氨基醇。二乙基锌与苯甲醛的氨基醇5或6介导的对映选择性加成反应以良好的收率形成了旋光性仲醇。当使用衍生自（+）-樟脑的催化剂时，以高ee获得（S）-醇，而与（-）-雄酮衍生的催化剂反应获得（R）-醇。

  DOI：

  10.1016/s0957-4166(00)00393-1
• 作为产物：
  描述：

  2-[(1R,2S,4R)-2-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]acetic acid 在 碘 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到(1S,5R,7R)-5,6,6-trimethyl-4-oxatricyclo[5.2.1.01,5]decan-3-one
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to aldehydes catalyzed by optically active 1,4-aminoalcohols

  摘要：

  Enantioselective addition reactions of diethylzinc to aldehydes were performed by catalytic reactions with chiral 1,4-aminoalcohols, Optically active 1,4-aminoalcohols were synthesized from (+)-camphor and (-)-fenchone through foul steps involving iodine-mediated lactonization of 3-hydroxy acids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00263-9

文献信息

• Iodine Mediated Lactonization of Terpenic 3-Hydroxy Acids
  作者：Tsutomu Fujita、Naoto Hanyu、Takashi Mino、Masami Sakamoto

  DOI：10.1055/s-2001-17513

  日期：——

  Cyclization of terpenic 3-hydroxy acids in the presence of a catalytic amount of iodine gave bicyclic or tricyclic lactones in good yield.

  在催化量的碘存在下，萜烯3-羟基酸的环化以良好的收率得到双环或三环内酯。
• Enantioselective addition of diethylzinc to aldehydes catalyzed by optically active 1,4-aminoalcohols
  作者：Naoto Hanyu、Tasuku Aoki、Takashi Mino、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/s0957-4166(00)00263-9

  日期：2000.7

  Enantioselective addition reactions of diethylzinc to aldehydes were performed by catalytic reactions with chiral 1,4-aminoalcohols, Optically active 1,4-aminoalcohols were synthesized from (+)-camphor and (-)-fenchone through foul steps involving iodine-mediated lactonization of 3-hydroxy acids. (C) 2000 Elsevier Science Ltd. All rights reserved.
• New chiral 1,4-aminoalcohols derived from (+)-camphor and (−)-fenchone for the enantioselective addition of diethylzinc to aldehyde
  作者：Naoto Hanyu、Tasuku Aoki、Takashi Mino、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/s0957-4166(00)00393-1

  日期：2000.10

  synthesized from (+)-camphor and (−)-fenchone. The aminoalcohols 5 or 6-mediated enantioselective addition reactions of diethylzinc to benzaldehyde resulted in the formation of the optically active secondary alcohol in good yield. When the catalyst derived from (+)-camphor was used, the (S)-alcohol was obtained in high ee, while the (R)-alcohol was obtained in the reaction with the catalyst derived from (−)-fenchone

  从（+）-樟脑和（-）-甲烯酮合成了各种旋光的1,4-氨基醇。二乙基锌与苯甲醛的氨基醇5或6介导的对映选择性加成反应以良好的收率形成了旋光性仲醇。当使用衍生自（+）-樟脑的催化剂时，以高ee获得（S）-醇，而与（-）-雄酮衍生的催化剂反应获得（R）-醇。