(R)-(+)-2-methylcyclopentadecanone | 52914-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-2-methylcyclopentadecanone
• 英文别名: (r)-2-Methylcyclopentadecanone；(2R)-2-methylcyclopentadecan-1-one
• CAS: 52914-66-6；77857-86-4；77857-73-9
• 化学式: C₁₆H₃₀O
• 分子量: 238.414
• InChiKey: XJDBBMWXVYBUTB-OAHLLOKOSA-N

物化性质

• 沸点：
  341.02°C (rough estimate)
• 密度：
  0.9213

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (R)-(+)-2-methylcyclopentadecanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以42%的产率得到(R)-(-)-15-hexadecanolide
  参考文献：
  名称：

  摘要：

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.

  DOI：

  10.1023/a:1022307600446
• 作为产物：
  描述：

  (S)-1-amino-2-(methoxymethyl)pyrrolidine 在 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 33.0h， 生成 (R)-(+)-2-methylcyclopentadecanone
  参考文献：
  名称：

  摘要：

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.

  DOI：

  10.1023/a:1022307600446

文献信息

• Exaltone® (=Cyclopentadecanone) from Isomuscone® (=Cyclohexadecanone), a One-C-Atom Ring-Contraction Methodology via a Stereospecific Favorskii Rearrangement: Regioselective Application to (−)-(R)-Muscone
  作者：Christian Chapuis、Fabrice Robvieux、Carole Cantatore、Christine Saint-Léger、Laurent Maggi

  DOI：10.1002/hlca.201100398

  日期：2012.3

  Treatment of cyclohexadecanone (1g; with I2 (2.2 mol‐euqiv.) and KOH in MeOH) furnished the unsaturated (Z)‐ester 2g in 83% yield, via a stereospecific Favorskii rearrangement (Scheme 1). Further treatment with 3‐chloroperbenzoic acid (m‐CPBA) afforded the unreported epoxy ester 3g (88% yield), which was cleaved in 33% yield to Exaltone® (=cyclopentadecanone; 1f) with NaOH in MeOH/H2O and then HCl

  环己癸酮（1g ;用I 2（2.2 mol-euqiv。）和KOH在MeOH中的溶液）的处理通过立体定向Favorskii重排提供了2％的不饱和（Z）-酯2g（方案1）。用3-氯过苯甲酸（进一步处理米-CPBA），得到未报告的环氧酯3克（88％产率），将其在33％产率，以裂解Exaltone ®（=环十五; 1F）用NaOH在MeOH / H 2 O和然后HCl在65°。该方法类似地扩展到较高的温度（C 17）和较低的温度（C 15C 11）的环状酮类似物，以及对（-）-（R）-muscone（5c）和homomuscone（5f）的区域选择性（方案2）。相应的大环-1-氧杂螺的嗅觉特性[2，Ñ ]烷烃和烯烃4和8，从所得到的科里 Chaykovsky oxiranylation，还提出。
• An asymmetric synthesis of acyclic and macrocyclic .alpha.-alkyl ketones. The role of (e)- and (z)-lithioenamines
  作者：A. I. Meyers、Donald R. Williams、Steven White、Gary W. Erickson

  DOI：10.1021/ja00401a029

  日期：1981.6
• MEYERS A. I.; WILLIAMS D. R.; WHITE S.; ERICKSON G. W., J. AMER. CHEM. SOC., 1981, 103, NO 11, 3088-3093
  作者：MEYERS A. I.、 WILLIAMS D. R.、 WHITE S.、 ERICKSON G. W.

  DOI：——

  日期：——