2-propylidenecyclohexanone | 60386-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propylidenecyclohexanone
• 英文别名: (2E)-2-propylidenecyclohexan-1-one
• CAS: 60386-54-1
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: AZOKXMIHWQXFBU-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-propylidenecyclohexanone 在 四氧化锇 、 磺酰氯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 作用下， 以 2,2,2-三氟乙醇 为溶剂， 生成 (1R,2S,5R,6S)-1-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-11-oxa-tricyclo[4.3.1.1^2,5]undec-3-en-10-one
  参考文献：
  名称：

  Diastereocontrol of [4 + 3] Cyclic Oxyallyl Cycloadditions by Alkoxy Substituents

  摘要：

  DOI：

  10.1021/jo990262n
• 作为产物：
  描述：

  (1R,3R)-1-Methyl-spiro[2.5]octan-4-one 生成 2-propylidenecyclohexanone
  参考文献：
  名称：

  Khazanie,P.G.; Lee-Ruff,E., Canadian Journal of Chemistry, 1978, vol. 56, p. 808 - 813

  摘要：

  DOI：

文献信息

• Asymmetric Transformation of Enones with<i>Synechococcus</i>sp. PCC 7942
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada、Shin-ya Yamane、Toshifumi Hirata

  DOI：10.1246/bcsj.77.2269

  日期：2004.12

  transformation of enones was investigated with cultured cells of Synechococcus sp. PCC 7942 (a cyanobacterium). The cells reduced both the endocyclic C-C double bond of s-trans enones and the exocyclic C-C double bond of s-cis enones with high enantioselectivity to afford optically active α-substituted (S)-ketones under illumination. In addition, the reduction of the double bond of these enones was accompanied

  用聚球藻的培养细胞研究了烯酮的不对称转化。PCC 7942（一种蓝细菌）。细胞以高对映选择性减少了 s-trans enones 的内环 CC 双键和 s-cis enones 的外环 CC 双键，以在光照下提供光学活性的 α-取代 (S)-酮。此外，这些烯酮双键的还原伴随着饱和醇的形成。细胞优先将简单的脂肪酮而不是环状酮还原为相应的（S）-醇，具有出色的对映选择性。
• A Novel Reductase Participating in the Hydrogenation of an Exocyclic C–C Double Bond of Enones from<i>Nicotiana tabacum</i>
  作者：Kei Shimoda、Shunsuke Izumi、Toshifumi Hirata

  DOI：10.1246/bcsj.75.813

  日期：2002.4

  A novel 74 kDa enone reductase which catalyzes the reduction of the exocyclic C–C double bond of enones was isolated from cultured cells of Nicotiana tabacum. The reductase was found to catalyze the enantiofacially selective reduction of the C–C double bond of 2-alkylidenecyclohexanone to give optically active (S)-2-alkylcyclohexanone.

  从培养的烟草（Nicotiana tabacum）细胞中分离出一种新型的74 kDa烯酮还原酶，该酶能催化烯酮的外环C–C双键的还原。研究发现，这种还原酶能够催化2-烷叉环己酮的C–C双键进行面选择性还原，生成光学活性的（S）-2-烷基环己酮。
• An Efficient Procedure for the Preparation of (<i>E</i>)-α-Alkylidenecycloalkanones Mediated by a CeCl₃·7H₂O−NaI System. Novel Methodology for the Synthesis of (<i>S</i>)-(−)-Pulegone¹
  作者：Giuseppe Bartoli、Marcella Bosco、Renato Dalpozzo、Arianna Giuliani、Enrico Marcantoni、Tiziana Mecozzi、Letizia Sambri、Elisabetta Torregiani

  DOI：10.1021/jo026418s

  日期：2002.12.1

  synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective beta-elimination reaction to (E)-2-alky

  2-亚烷基环烷酮是强大的合成子，在许多重要合成中用作关键中间体。由于它们的潜力，人们认为在非常温和的条件下用容易获得的起始原料进行制备的一般方法是值得的。七水合氯化铈（III）与碘化钠在回流的乙腈中促进2-和（1-羟烷基）环烷酮中的（E）-2-亚烷基环烷酮的区域和立体选择性β消除反应。本方法的合成值通过光学活性形式的单萜（S）-（-）-普勒高酮（8）的合成来证明。
• Spiro compounds as perfuming ingredients
  申请人：——

  公开号：US20040072721A1

  公开（公告）日：2004-04-15

  The present invention relates to the perfumery industry. It concerns more particularly an alcohol, ester, ether or ketone derivative having a spiro-type skeleton, the latter being substituted by short alkyl groups. The invention also relates to the use of the invention compounds as perfuming ingredients, able to impart a woody and/or aromatic, as well as to the perfumed articles or perfuming compositions comprising as active ingredient a compound of formula (I).

  本发明涉及香精工业。它更具体地涉及一种醇、酯、醚或酮衍生物，其具有螺环型骨架，后者被短链烷基基团取代。该发明还涉及将该发明化合物用作香精成分，能够赋予木质和/或芳香性，并且涉及含有作为活性成分的化合物的香水制品或香水组合物。
• Asymmetric Hydrogenation of the C–C Double Bond of Enones with the Reductases from<i>Nicotiana tabacum</i>
  作者：Toshifumi Hirata、Kei Shimoda、Takayuki Gondai

  DOI：10.1246/cl.2000.850

  日期：2000.8

  Three enone reductases, p44, p74, and p90, from the cultured cells of Nicotiana tabacum catalyzed the asymmetric hydrogenation of the C–C double bond of enones. Reduction of 2-alkyl-2-cyclohexen-1-ones with the p44 reductase gave highly optically active (R)-2-alkylcyclohexanones, whereas reaction with the p90 reductase gave (S)-2-alkylcyclohexanones. On the other hand, reduction of 2-alkylidenecyclohexanones with the p74 reductase gave (S)-2-alkylcyclohexanones.

  来自烟草培养细胞的三种烯酮还原酶（p44、p74 和 p90）催化了烯酮 C-C 双键的不对称氢化反应。用 p44 还原酶还原 2-烷基-2-环己烯-1-酮可得到光学活性很高的（R）-2-烷基环己酮，而用 p90 还原酶反应可得到（S）-2-烷基环己酮。另一方面，用 p74 还原酶还原 2-亚烷基环己酮可得到 (S)-2-烷基环己酮。