二烯丙醇缩环己酮 | 53608-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 二烯丙醇缩环己酮
• 英文名称: Cyclohexanon-diallylketal
• 英文别名: 1,1-Bis[(prop-2-en-1-yl)oxy]cyclohexane；1,1-bis(prop-2-enoxy)cyclohexane
• CAS: 53608-84-7
• 化学式: C₁₂H₂₀O₂
• mdl: MFCD03425839
• 分子量: 196.29
• InChiKey: GHWPMYGCPQBQBX-UHFFFAOYSA-N

物化性质

• 沸点：
  253.5±20.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909209000

反应信息

• 作为反应物：
  描述：

  二烯丙醇缩环己酮 在 二乙基碘化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以58%的产率得到1-(2-丙烯-1-氧基)环己烯
  参考文献：
  名称：

  有机铝试剂促进脂肪族克莱森重排

  摘要：

  有机铝化合物 R3Al 在室温下在 R 或 H 作为亲核试剂转移到醛碳的情况下促进烯丙基乙烯基醚衍生物的克莱森重排。在 25 °C 下，用 Me3Al（1.0 M，2.2 当量）在 CH2ClCH2Cl 中的己烷溶液处理 1-丁基-2-丙烯基乙烯基醚得到 5-癸烯-2-醇（产率 91%，E⁄Z=47⁄53 )，这是由 [3,3] sigmatropic 重排和连续甲基化产生的。还实现了炔基化、烯基化和氢化的重排。使用 Et2AlSPh（2.5 equiv）或 Et2AlCl（2.0 equiv）和 PPh3（2.2 equiv）的组合，在 25 °C 下获得了常规的 Claisen 重排产物或 γ,δ-不饱和醛（酮）。

  DOI：

  10.1246/bcsj.57.446
• 作为产物：
  描述：

  乙酰丙酸甲酯 以89%的产率得到
  参考文献：
  名称：

  Brogan John B., Richard Judson E., Zercher Charles K., Synth. Commun., 25 (1995) N 4, S 587- 593

  摘要：

  DOI：

文献信息

• Preparation of Diallyl Ketals
  作者：John B. Brogan、Judson E. Richard、Charles K. Zercher

  DOI：10.1080/00397919508011393

  日期：1995.2

  Abstract A general method for the preparation of diallyl acetals and ketals is reported. The reaction is performed well below room temperature, thereby eliminating any competing Claisen rearrangement. These mild reaction conditions also facilitate ketal formation on methyl levulinate 1 with no transesterification.

  摘要 报道了制备二烯丙基缩醛和缩酮的通用方法。该反应在远低于室温的条件下进行，从而消除了任何竞争性克莱森重排。这些温和的反应条件也有利于在乙酰丙酸甲酯 1 上形成缩酮，而无需进行酯交换。
• METHOD FOR PRODUCING ALPHA-ALLYLATED CYCLOALKANONE
  申请人：Kao Corporation

  公开号：US20220153672A1

  公开（公告）日：2022-05-19

  Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion. where R 1 , R 2 , and R 3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A 1 - (it should be noted that the front bond refers to a bond that binds to the carbon atom C 1 and the back bond refers to a bond that binds to the carbon atom C 2 ) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R 4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

  提供的是一种方法，通过使用宏环化合物作为起始物质，得到α-烯丙基化环戊酮。该方法是一种生产通式（IV）所表示的α-烯丙基化环戊酮的方法，该方法包括将通式（I）所表示的化合物和/或通式（II）所表示的化合物与通式（III）所表示的化合物在酸催化剂存在下反应，以产生通式（IV）所表示的α-烯丙基化环戊酮，其中酸催化剂包括含有铵阳离子和阴离子的酸催化剂。其中，R1、R2和R3相同或不同，且均为具有1个或多个碳原子和4个或更少碳原子的烷基；-A1-（应注意前面的键指与碳原子C1结合的键，后面的键指与碳原子C2结合的键）为具有4个或更多碳原子和20个或更少碳原子的烷基，可选地含有杂原子和可选地具有取代基；R4为氢原子或具有1个或多个碳原子和4个或更少碳原子的烷基。
• METHOD FOR PRODUCING alpha- ALLYLATED CYCLOALKANONE
  申请人：Kao Corporation

  公开号：EP3943476A1

  公开（公告）日：2022-01-26

  Provided is a method with which an α-allylated cycloalkanone is obtained from a macrocyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion. where R1, R2, and R3 are the same or different and each of them is an alkyl group having 1 or more and 4 or less of carbon atoms, the group -A1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C1 and the back bond refers to a bond that binds to the carbon atom C2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

  本发明提供了一种从用作起始原料的大环化合物中获得α-烯丙基环烷酮的方法。该方法是一种生产通式（IV）代表的α-烯丙基环烷酮的方法，该方法包括以下步骤：在酸催化剂存在下，通式（I）代表的化合物和/或通式（II）代表的化合物与通式（III）代表的化合物反应，生成通式（IV）代表的α-烯丙基环烷酮，酸催化剂包括一种包括铵阳离子和阴离子的酸催化剂。 其中 R1、R2 和 R3 相同或不同，且各自为具有 1 个或 1 个以上和 4 个或 4 个以下碳原子的烷基，基团-A1-（应注意，前键指与碳原子 C1 结合的键，后键指与碳原子 C2 结合的键）为具有 4 个或 4 个以上和 20 个或 20 个以下碳原子的亚烷基，该亚烷基可选择含有一个杂原子，并可选择具有一个取代基，R4 为氢原子或具有 1 个或 1 个以上和 4 个或 4 个以下碳原子的烷基。
• METHOD FOR PRODUCING ALPHA-ALLYLATION CYCLOALKANONE
  申请人：Kao Corporation

  公开号：EP3943477A1

  公开（公告）日：2022-01-26

  Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C1 and the back bond refers to a bond that binds to the carbon atom C2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

  本发明提供了一种从用作起始原料的环状化合物环烷酮中获得α-烯丙基环烷酮的方法。该方法是一种生产通式（III）代表的 α-烯丙基环烷酮的方法，该方法包括： 步骤 1：在第一酸催化剂和可选的脱水剂存在下，使通式（I）代表的化合物和具有 1 个或 1 个以上和 4 个或 4 个以下碳原子的醇反应；以及 步骤 2：在第二酸催化剂存在下，使步骤 1 中得到的粗产物和通式（II）代表的化合物反应，生成通式（III）代表的 α-烯丙基环烷酮。步骤 1 和步骤 2 连续进行。在上式中，基团-A1-（应注意，前键是指与碳原子 C1 结合的键，后键是指与碳原子 C2 结合的键）是具有 4 个或 4 个以上、20 个或 20 个以下碳原子的亚烷基，该亚烷基可选择含有一个杂原子，并可选择具有一个取代基，R4 是氢原子或具有 1 个或 1 个以上、4 个或 4 个以下碳原子的烷基。
• Method for producing alpha-allylated cycloalkanone
  申请人：Kao Corporation

  公开号：US11524929B2

  公开（公告）日：2022-12-13

  Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A 1 - (it should be noted that the front bond refers to a bond that binds to the carbon atom C 1 and the back bond refers to a bond that binds to the carbon atom C 2 ) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R 4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

  本发明提供了一种从用作起始原料的环状化合物环烷酮中获得α-烯丙基环烷酮的方法。该方法是一种生产通式（III）代表的 α-烯丙基环烷酮的方法，该方法包括： 步骤 1：在第一酸催化剂和可选的脱水剂存在下，使通式（I）代表的化合物和具有 1 个或 1 个以上和 4 个或 4 个以下碳原子的醇反应；以及 步骤 2：在第二酸催化剂存在下，使步骤 1 中得到的粗产物和通式（II）代表的化合物反应，生成通式（III）代表的 α-烯丙基环烷酮。步骤 1 和步骤 2 连续进行。在上式中，基团 -A 1 - 应注意，前键是指与碳原子 C 1 的键，后键指与碳原子 C 2 ）是一个碳原子数为 4 个或 4 个以上、20 个或 20 个以下的亚烷基，该亚烷基可选择含有一个杂原子，并可选择具有一个取代基，且 R 4 是氢原子或具有 1 个或 1 个以上、4 个或 4 个以下碳原子的烷基。