(1S,2R,4R)-1-methyl-4-(1-oxoethyl)cyclohexane 1,2-oxide | 57129-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,2R,4R)-1-methyl-4-(1-oxoethyl)cyclohexane 1,2-oxide
• 英文别名: (1s,2r,4r)-cis-4-Acetyl-1,2-epoxy-1-methylcyclohexane；1-[(1R,3R,6S)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl]ethanone
• CAS: 57129-05-2
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: VPQYGKRHSKLXJB-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-1-methyl-4-(1-oxoethyl)cyclohexane 1,2-oxide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以70%的产率得到(4S)-1-甲基-4-乙酰氧基环己烷1,2-氧化物
  参考文献：
  名称：

  （S）-和（R）-1-甲基-2-环己烯-1-醇的新合成方法：树突状拟tsu的聚集信息素。

  摘要：

  DOI：

  10.1021/jo951440p
• 作为产物：
  描述：

  甜橙提取物 在 二甲基硫 、 碳酸氢钠 、 臭氧 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (1S,2R,4R)-1-methyl-4-(1-oxoethyl)cyclohexane 1,2-oxide
  参考文献：
  名称：

  Trichodiene synthase. Synergistic inhibition by inorganic pyrophosphate and aza analogs of the bisabolyl cation.

  摘要：

  A series of aza analogs of the bisabolyl and alpha-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase. Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone. In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40. The apparent induced inhibition constant alpha-K(j) decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog. The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.

  DOI：

  10.1021/jo00038a040

文献信息

• Identification and synthesis of (Z)-(1′S,3′R,4′S)(–)-2-(3′,4′-epoxy-4′-methylcyclohexyl)-6-methylhepta-2,5-diene, the sex pheromone of the southern green stinkbug, Nezara viridula(L.)
  作者：Raymond Baker、Miguel Borges、Nigel G. Cooke、Richard H. Herbert

  DOI：10.1039/c39870000414

  日期：——

  The sex pheromone of the male green stinkbug, Nezara viridula(L.) has been shown to be a novel epoxybisabolene (Z)-(1′S,3′R,4′S)(–)-2-(3′,4′-epoxy-4′-methylcyclohexyl)-6-methylhepta-2,5-diene, whose structure has been confirmed by spectroscopic studies and synthesis of the eight possible stereoisomers.

  阳绿椿象的性信息素，稻绿蝽（L.）已被证明是一种新颖epoxybisabolene（Ž） - （1'小号，3' - [R，4'小号）（ - ） - 2-（3'， 4'-环氧-4'-甲基环己基）-6-甲基庚-2,5-二烯的结构已通过光谱研究和八种可能的立体异构体的合成得到证实。
• Stereocontrolled Synthesis of the Sex Pheromones of the Green Stink Bug
  作者：B. E. Marron、K. C. Nicolaou

  DOI：10.1055/s-1989-27309

  日期：——

  The four diastereoisomeric 3′,4′-epoxides of (Z)-α-bisabolene, (+)-1, (+)-2, (-)-1 and (+)-2, have been synthesized by stereocontrolled sequences. Comparisons with natural materials collected from the stink bug Nezara viridula revealed that the pheromone blend of this species contains (+)-1 or (-)-2 as major epoxide and (+)-2 or (-)-1 as minor epoxide in varying ratios depending on the geographical site of collection.

  通过立体控制序列合成了(Z)-δ-bisabolene的四种非对映异构体3′,4′-环氧化物，即(+)-1、(+)-2、(-)-1和(+)-2。通过与从蝽类 Nezara viridula 采集的天然材料进行比较，发现该物种的信息素混合物中主要环氧化物为 (+)-1 或 (-)-2，次要环氧化物为 (+)-2 或 (-)-1，其比例因采集地点而异。
• Selenoxides as Leaving Groups: Synthesis of Epoxides
  作者：P Ceccherelli

  DOI：10.1016/00404-0399(50)09448-

  日期：1995.7.10

  beta-Hydroxyselenoxides, prepared from substituted cyclohexenes, have been selectively transformed into chiral epoxides by treatment with alkali.
• MARRON, B. E.;NICOLAOU, K. C., SYNTHESIS (BRD),(1989) N, C. 537-539
  作者：MARRON, B. E.、NICOLAOU, K. C.

  DOI：——

  日期：——
• Trichodiene synthase. Synergistic inhibition by inorganic pyrophosphate and aza analogs of the bisabolyl cation.
  作者：David E. Cane、Guohan Yang、Robert M. Coates、Hyung Jung Pyun、Thomas M. Hohn

  DOI：10.1021/jo00038a040

  日期：1992.6

  A series of aza analogs of the bisabolyl and alpha-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase. Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone. In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40. The apparent induced inhibition constant alpha-K(j) decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog. The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.