3,3,5-trimethylcyclopentane-1,2-diol | 1215117-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,5-trimethylcyclopentane-1,2-diol
• 英文别名: 3,3,5-Trimethylcyclopentane-1,2-diol
• CAS: 1215117-76-2
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: GYMVXTJTIMRJFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3,5-trimethylcyclopentane-1,2-diol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到2-hydroxy-3,5,5-trimethylcyclopent-2-enone
  参考文献：
  名称：

  Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one

  摘要：

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.

  DOI：

  10.1002/hlca.200900231
• 作为产物：
  描述：

  3,5,5-三甲基-2-环戊烯-1-酮 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以61%的产率得到3,3,5-trimethylcyclopentane-1,2-diol
  参考文献：
  名称：

  Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one

  摘要：

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.

  DOI：

  10.1002/hlca.200900231

文献信息

• Method for preparing ethers of cycloaliphatic or araliphatic diols
  申请人：BASF SE

  公开号：US11078146B2

  公开（公告）日：2021-08-03

  The present invention relates to a method for preparing a dialkyi or dialkenyl ether of a cycloaliphatic or araliphatic diol, which comprises (i) reacting the cycloaliphatic or araliphatic diol with metallic sodium in an aprotic organic solvent in the presence of a catalytic amount of at least one monoether-monoalcohol of formula (I) wherein Y is identical or different and selected from C2-C4-alkylene, n is an integer in the range from 1 to 10, and R1 is C1-C4-Alkyl, whereby the corresponding disodium dialcoholate is obtained, reacting the disodium dialcoholate obtained in step (i) with an alkylation alkenylation reagent.

  本发明涉及一种制备环脂族或脂肪族二元醇的二酮基或二烯基醚的方法，其包括 (i) 在催化量的至少一种式(I)的单醚一元醇存在下，在非沸腾有机溶剂中使环脂族或脂肪族二元醇与金属钠反应，式(I)中Y为相同或不同且选自C2-C4-烯烃、n 为 1-10 之间的整数，R1 为 C1-C4 烷基，将步骤(i)中得到的二醇二钠与烷基化烯基化试剂反应，可得到相应的二醇二钠。
• METHOD FOR PREPARING ETHERS OF CYCLOALIPHATIC OR ARALIPHATIC DIOLS
  申请人：BASF SE

  公开号：EP3720835B1

  公开（公告）日：2022-07-13
• Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one
  作者：Christian Chapuis、Christine Saint-Léger

  DOI：10.1002/hlca.200900231

  日期：2010.1

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.