[R-(Z)]-5-异丙基-8-甲基壬-6,8-二烯-2-酮 | 99745-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [R-(Z)]-5-异丙基-8-甲基壬-6,8-二烯-2-酮
• 英文名称: [R-(Z)]-5-isopropyl-8-methylnona-6,8-dien-2-one
• 英文别名: (5R,6Z)-8-methyl-5-propan-2-ylnona-6,8-dien-2-one
• CAS: 99745-11-6
• 化学式: C₁₃H₂₂O
• 分子量: 194.31
• InChiKey: PQDRXUSSKFWCFA-FWPCIQOSSA-N

物化性质

• 沸点：
  269.0±19.0 °C(Predicted)
• 密度：
  0.846±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

文献信息

• (z)-solanone, and preparation process and use thereof
  申请人：CHINA TOBACCO YUNNAN INDUSTRIAL CO., LTD

  公开号：US11198665B1

  公开（公告）日：2021-12-14

  A (Z)-solanone has the steric formula of: or with the name of (S,Z)-5-isopropyl-8-methyl-6,8-diene-2-one or (R,Z)-5-isopropyl-8-methyl-6,8-diene-2-one. A process for the preparation of the (Z)-type solanone and the use thereof in flavoring of cigarette shred are further disclosed. The process includes the following steps: (1) reacting isopentanal and methyl vinyl ketone, under the action of a catalyst and a co-catalyst, to give (S)-2-isopropyl-5-carbonylhexanal or (R)-2-isopropyl-5-carbonylhexanal; (2) reacting the (S)-2-isopropyl-5-carbonylhexanal or the (R)-2-isopropyl-5-carbonylhexanal obtained in step (1) with (iodomethyl)triphenylphosphonium iodide, to give (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or (R,Z)-7-iodo-5-isopropyl-6-ene-2-one; and (3) reacting the (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or the (R,Z)-7-iodo-5-isopropyl-6-ene-2-one obtained in step (2) with pinacol isopropenylborate in the presence of a catalyst to give the (Z)-solanone.

  (Z)-索拉酮的立体结构式为 或 (S,Z)-5-异丙基-8-甲基-6,8-二烯-2-酮或(R,Z)-5-异丙基-8-甲基-6,8-二烯-2-酮。进一步公开了制备 (Z) 型茄酮的工艺及其在香烟切片香料中的用途。该工艺包括以下步骤：(1) 在催化剂和助催化剂的作用下，使异戊醛和甲基乙烯基甲酮反应，得到(S)-2-异丙基-5-羰基己醛或(R)-2-异丙基-5-羰基己醛；(2) 将步骤(1)中得到的(S)-2-异丙基-5-甲酰己醛或(R)-2-异丙基-5-甲酰己醛与(碘甲基)三苯基碘化鏻反应，得到(S,Z)-7-碘-5-异丙基-6-烯-2-酮或(R,Z)-7-碘-5-异丙基-6-烯-2-酮；(3) 在催化剂存在下，将步骤(2)中得到的(S,Z)-7-碘-5-异丙基-6-烯-2-酮或(R,Z)-7-碘-5-异丙基-6-烯-2-酮与异丙烯硼酸频哪醇酯反应，得到(Z)-solanone。
• (Z)-SOLANONE, AND PREPARATION PROCESS AND USE THEREOF
  申请人：CHINA TOBACCO YUNNAN INDUSTRIAL CO., LTD

  公开号：US20210380517A1

  公开（公告）日：2021-12-09

  A (Z)-solanone has the steric formula of: with the name of (S,Z)-5-isopropyl-8-methyl-6,8-diene-2-one or (R,Z)-5-isopropyl-8-methyl-6,8-diene-2-one. A process for the preparation of the (Z)-type solanone and the use thereof in flavoring of cigarette shred are further disclosed. The process includes the following steps: (1) reacting isopentanal and methyl vinyl ketone, under the action of a catalyst and a co-catalyst, to give (S)-2-isopropyl-5-carbonylhexanal or (R)-2-isopropyl-5-carbonylhexanal; (2) reacting the (S)-2-isopropyl-5-carbonylhexanal or the (R)-2-isopropyl-5-carbonylhexanal obtained in step (1) with (iodomethyl)triphenylphosphonium iodide, to give (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or (R,Z)-7-iodo-5-isopropyl-6-ene-2-one; and (3) reacting the (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or the (R,Z)-7-iodo-5-isopropyl-6-ene-2-one obtained in step (2) with pinacol isopropenylborate in the presence of a catalyst to give the (Z)-solanone.