2-(1-hydroxyheptyl)cyclopentanone | 93430-30-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(1-hydroxyheptyl)cyclopentanone
• 英文别名: 2-(α-Hydroxy-heptyl)-cyclopentanon；Cyclopentanone, 2-(1-hydroxyheptyl)-；2-(1-hydroxyheptyl)cyclopentan-1-one
• CAS: 93430-30-9
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: VZAPPURGJHNQTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxyheptyl)cyclopentanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 以94%的产率得到2-亚庚基环戊酮(6CI,9CI)
  参考文献：
  名称：

  Reactions of Tin(IV) Enolates Obtained from O-Stannyl Ketyls under Neutral Free Radical Conditions

  摘要：

  Under mild and neutral free radical conditions, an alpha,beta-unsaturated ketone reacted with tributyltin hydride to produce an intermediate resonance-stabilized allylic O-stannyl ketyl. Upon subsequent hydrogen atom abstraction, a tin(IV) enolate was afforded which could be quenched with a variety of electrophiles and form new carbon-carbon bonds. Aldehydes react to produce aldol-type products and both intramolecular and intermolecular carbonyl addition reactions were investigated using this strategy. Using similar methodology, the tin(TV) enolate could be quenched in the presence of HMPA with various alkyl halides and alpha,beta-unsaturated carbonyl compounds (Michael accepters) to yield alkylated products in good yields. These reactions represent a very mild regioselective alternative to metal enolate formation which usually requires strong bases such as LDA or strongly reductive dissolving metal conditions to achieve success. New carbon skeletons for natural product synthesis can be readily constructed using this chemically neutral approach.

  DOI：

  10.1021/jo960639e
• 作为产物：
  描述：

  庚醛 、 环戊酮 在 sodium hydroxide 、 溶剂黄146 作用下， 以 正己烷 、 水 为溶剂， 生成 2-(1-hydroxyheptyl)cyclopentanone
  参考文献：
  名称：

  Process for producing 2-alkyl-2cyclopentenones

  摘要：

  从环戊酮和羰基化合物获得的2-(1-羟基烷基)环戊酮或2-烷基亚烯环戊酮，是从高产率开始生产2-烷基-2-环戊酮的工业上有利的过程。在以下一般式（1）中表示的2-(1-羟基烷基)环戊酮中（其中R1、R2、R3、R4、R5、R6和R7分别独立地表示氢原子、具有1至10个碳原子的烷基基团，可能具有一个或多个取代基或可能具有一个或多个取代基的芳香基团，且(1) R6或R7与R3和(2) R6或R7与R4或R5中的每一个可能结合在一起形成可能具有双键的环)在溴化合物和/或碘化合物的存在下进行脱水异构化。

  公开号：

  US20030109755A1

文献信息

• Intermolecular aldol reactions via allylic o-stannyl ketyls
  作者：Eric J. Enholm、Paul E. Whitley

  DOI：10.1016/0040-4039(95)01999-x

  日期：1995.12

  A mild and neutral free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A tin(IV) enolate, produced by subsequent hydrogen atom transfer, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new α,β-unsaturated ketones with E/Z

  α，β-不饱和酮与三丁基锡自由基的温和中性自由基反应产生了共振稳定的烯丙基O-锡烷基酮基中间体。接下来，通过随后的氢原子转移生成的锡（IV）烯醇锡，再用各种醛淬灭，生成羟醛产物，可以很容易地用对甲苯磺酸消除，得到新的α/β-不饱和酮，其E / Z比最高为> 100：1。
• Process for producing 2-alkyl-2cyclopentenones
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20030109755A1

  公开（公告）日：2003-06-12

  Industrially advantageous processes for producing a 2-alkyl-2-cyclopentenone in high yields starting from a 2-(1-hydroxyalkyl)cyclopentanone or a 2-alkylidenecyclopentanone, which are obtainable from a cyclopentanone and a carbonyl compound. A 2-(1-hydroxyalkyl)cyclopentanone represented by the following general formula (1): 1 (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 each independently represents hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have one or more substituents or an aromatic group which may have one or more substituents, and each of (1) R 6 or R 7 with R 3 and (2) R 6 or R 7 with R 4 or R 5 may be together combined to form a ring which may have a double bond) is subjected to dehydrative isomerization in the presence of a bromine compound and/or an iodine compound.

  从环戊酮和羰基化合物获得的2-(1-羟基烷基)环戊酮或2-烷基亚烯环戊酮，是从高产率开始生产2-烷基-2-环戊酮的工业上有利的过程。在以下一般式（1）中表示的2-(1-羟基烷基)环戊酮中（其中R1、R2、R3、R4、R5、R6和R7分别独立地表示氢原子、具有1至10个碳原子的烷基基团，可能具有一个或多个取代基或可能具有一个或多个取代基的芳香基团，且(1) R6或R7与R3和(2) R6或R7与R4或R5中的每一个可能结合在一起形成可能具有双键的环)在溴化合物和/或碘化合物的存在下进行脱水异构化。
• Process for producing 2-alkyl-2-cyclopentenones
  申请人：Takasago International Corporation

  公开号：EP1316541A1

  公开（公告）日：2003-06-04

  Industrially advantageous processes for producing a 2-alkyl-2-cyclopentenone in high yields starting from a 2-(1-hydroxyalkyl)cyclopentanone or a 2-alkylidenecyclopentanone, which are obtainable from a cyclopentanone and a carbonyl compound. A 2-(1-hydroxyalkyl)cyclopentanone represented by the following general formula (1): is subjected to dehydrative isomerization or a 2- alkylidenecyclopentanone represented by the following general formula (3): is isomerized. Both reactions take place in the presence of a bromine compound and/or an iodine compound. In the above formulae, R1-R7 have the meanings given in the description.

  以 2-(1-羟基烷基)环戊酮或 2-亚烷基环戊酮为原料，高产率生产 2-烷基-2-环戊酮的具有工业优势的工艺，这些环戊酮可从环戊酮和羰基化合物中获得。由以下通式 (1) 代表的 2-(1-羟基烷基)环戊酮： 的 2-(1-羟基烷基)环戊酮进行脱水异构化，或将以下通式(3)代表的 2-亚烷基环戊酮进行异构化： 进行异构化。这两种反应均在溴化合物和/或碘化合物存在下进行。 在上式中，R1-R7 具有说明中给出的含义。
• PROCESS FOR PRODUCING 2-ALKYLCYCLOALKANONE
  申请人：Kao Corporation

  公开号：EP2487150A1

  公开（公告）日：2012-08-15

  The present invention relates to a process for producing 2-alkylcycloalkanones with a high yield and a high purity. In addition, the present invention also relates to a process for producing lactones as a useful perfume material for cosmetics, flavors, etc. More specifically, the present invention relates to a process for producing a 2-alkylcycloalkanone represented by the following general formula (2) which includes the step of subjecting a 2-(1-hydroxyalkyl)-cycloalkanone to dehydration and hydrogenation reaction in a flow of a hydrogen gas under a pressure of from 20 to 200 kPa (absolute pressure) in the presence of an acid and a platinum group metal catalyst; and a process for producing a lactone which includes the step of subjecting the 2-alkylcycloalkanone to oxidation reaction using a percarboxylic acid: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.

  本发明涉及一种以高产率和高纯度生产 2-烷基环烷酮的工艺。此外，本发明还涉及一种生产内酯的工艺，这种内酯是一种有用的香水材料，可用于化妆品、香精等。更具体地说，本发明涉及一种生产由以下通式（2）代表的 2-烷基环烷酮的工艺，该工艺包括以下步骤：在一种酸和一种铂族金属催化剂存在下，使 2-（1-羟基烷基）-环烷酮在压力为 20 至 200 kPa（绝对压力）的氢气流中进行脱水和氢化反应；以及一种生产内酯的工艺，其中包括使用过羧酸使 2-烷基环烷酮进行氧化反应的步骤： 其中n为1或2的整数；R1和R2各自独立地为氢原子或具有1至8个碳原子的烷基，但R1和R2可通过相邻的碳原子形成环。
• PROCESS FOR PRODUCING A LACTONE
  申请人：Kao Corporation

  公开号：EP2487150B1

  公开（公告）日：2016-12-28