3-butylcitronellal | 70645-62-4

• 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: 3-butylcitronellal
• 英文别名: 3-Butyl-3,7-dimethyl-6-octenal；3-butyl-3,7-dimethyloct-6-enal
• CAS: 70645-62-4
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: WBTSUPQKRNMZIN-UHFFFAOYSA-N

物化性质

• 沸点：
  280.2±9.0 °C(Predicted)
• 密度：
  0.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-butylcitronellal 在 Al-MCM-41 作用下， 以 甲苯 为溶剂， 生成 5-n-butyl-5-methyl-2-(prop-1-en-2-yl)cyclohexanol
  参考文献：
  名称：

  BINOL-Al catalyzed kinetic resolution of citronellal analogues: synthesis of a variety of fragrances

  摘要：

  A chiral aluminum catalyst was used for the kinetic resolution of citronellal analogues. Racemic 3-alkyl-citronellals gave optically active 5-alkylisopulegols with high enantioselectivity. Unreacted 3-alkyl-citronellal analogues were obtained with low enantioselectivity. The two main diastereoisomers of the product were opposite to each other. The scents of 5-substituted isopulegols were evaluated. The chiral recognition of the catalysts and their effects on the kinetic resolutions are also discussed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.007
• 作为产物：
  描述：

  正丁基锂 、 柠檬醛 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以78%的产率得到3-butylcitronellal
  参考文献：
  名称：

  NOVEL LACTONE COMPOUND AND NOVEL ETHER COMPOUND

  摘要：

  一种内酯化合物由通式（A）表示，一种醚化合物由通式（B）表示。在通式（A）中，R是氢原子或R1。当R是氢原子时，R′是R1，碳键（1）是单键或双键，碳键（2）是单键。当R是R1时，R′是氢原子或R1，碳键（1）和（2）都是单键，或其中一个是双键，另一个是单键。在通式（B）中，R″是R1。R1代表一个特定的烷基基团，一个特定的烯基基团，一个特定的炔基基团或芳基。在通式（A）和（B）中，n为0或1。

  公开号：

  US20210047283A1

文献信息

• Organomanganese (II) reagents XVIII: Copper-catalyzed 1,4- addition of organomanganese chloride compounds to conjugated ethylenic aldehydes
  作者：Gérard Cahiez、Mouad Alami

  DOI：10.1016/s0040-4039(00)70698-8

  日期：1989.1

  Organomanganese chlorides react with β-mono or β,β-bisubstituted α,β-ethylenic aldehydes in the presence of a catalytic amount of copper chloride to give good yields of 1,4-addition products in THF at −30°C.

  在催化量的氯化铜存在下，有机锰氯化物与β-单取代或β，β-双取代的α，β-乙烯醛反应，在-30°C下的THF中提供1,4-加成产物的良好收率。
• Highly selective aluminium-catalysed intramolecular Prins reaction for <scp>l</scp>-menthol synthesis
  作者：H. Itoh、H. Maeda、S. Yamada、Y. Hori、T. Mino、Masami Sakamoto

  DOI：10.1039/c4ra12470g

  日期：——

  The perfect production of l-menthol.

  l-薄荷脑的完美生产。
• Correction: Highly selective aluminium-catalysed intramolecular Prins reaction for <scp>l</scp>-menthol synthesis
  作者：H. Itoh、H. Maeda、S. Yamada、Y. Hori、T. Mino、Masami Sakamoto

  DOI：10.1039/c5ra90068a

  日期：——

  Correction for ‘Highly selective aluminium-catalysed intramolecular Prins reaction for L-menthol synthesis’ by H. Itoh et al., RSC Adv., 2014, 4, 61619–61623.

  H. Itoh等人对“用于L-薄荷醇合成的高选择性铝催化的分子内Prins反应”的校正。，RSC Adv。，2014，4，61619-61623。
• NOVEL LACTONE COMPOUND AND NOVEL ETHER COMPOUND
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20210047283A1

  公开（公告）日：2021-02-18

  A lactone compound is represented by general formula (A), and an ether compound is represented by general formula (B). In formula (A), R is a hydrogen atom or R1. When R is a hydrogen atom, R′ is R1, the carbon bond (1) is a single bond or a double bond, and the carbon bond (2) is a single bond. When R is R1, R′ is a hydrogen atom or R1, both the carbon bonds (1) and (2) are a single bond, or one of them is a double bond and the other is a single bond. In formula (B), R″ is R1. R1 represents a specific alkyl group, a specific alkenyl group, a specific alkynyl group, or an aryl group. In formulas (A) and (B), n is 0 or 1.

  一种内酯化合物由通式（A）表示，一种醚化合物由通式（B）表示。在通式（A）中，R是氢原子或R1。当R是氢原子时，R′是R1，碳键（1）是单键或双键，碳键（2）是单键。当R是R1时，R′是氢原子或R1，碳键（1）和（2）都是单键，或其中一个是双键，另一个是单键。在通式（B）中，R″是R1。R1代表一个特定的烷基基团，一个特定的烯基基团，一个特定的炔基基团或芳基。在通式（A）和（B）中，n为0或1。
• BINOL-Al catalyzed kinetic resolution of citronellal analogues: synthesis of a variety of fragrances
  作者：Hisanori Itoh、Hironori Maeda、Shinya Yamada、Yoji Hori、Takashi Mino、Masami Sakamoto

  DOI：10.1016/j.tetasy.2016.06.007

  日期：2016.8

  A chiral aluminum catalyst was used for the kinetic resolution of citronellal analogues. Racemic 3-alkyl-citronellals gave optically active 5-alkylisopulegols with high enantioselectivity. Unreacted 3-alkyl-citronellal analogues were obtained with low enantioselectivity. The two main diastereoisomers of the product were opposite to each other. The scents of 5-substituted isopulegols were evaluated. The chiral recognition of the catalysts and their effects on the kinetic resolutions are also discussed. (C) 2016 Elsevier Ltd. All rights reserved.