(1RS,2RS,5RS)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1RS,2RS,5RS)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one
• 英文别名: trans-2-methyl-6-oxabicyclo<3.2.1>octan-7-one；trans-2-methyl-6-oxabicyclo[3.2.1]octan-7-one；(1R,2R,5R)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: RSRUWEWNWVYITP-FSDSQADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1RS,2RS,5RS)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one 在 甲基三氯硅烷 、 sodium iodide 、 sodium carbonate 作用下， 以 乙腈 、 四氢呋喃 为溶剂， 反应 2.83h， 以64%的产率得到(-)-(1R,2R,5R)-5-iodo-2-methylcyclohexanecarboxylic acid
  参考文献：
  名称：

  改进的顺式-5-碘-反式-2-甲基环己烷甲酸乙酯的合成，地中海果蝇的强力引诱剂

  摘要：

  由商业上可得到的外消旋反式方便地合成了外消旋的5-碘-2-甲基环己烷甲酸乙酯（1）（称为地中海果蝇引诱剂B 1）及其（-）-（1 R，2 R，5 R）对映体1a -6-甲基-3-环己烯羧酸2或其（1 R，6 R）对映异构体2a。关键步骤包括使用磺胺助剂进行不对称Diels-Alder反应，以及将不需要的反式-5-碘-反式-2-甲基环己烷羧酸环化（8）至中间体内酯7（或8a至7a）。新方法可能会绕过色谱分离，并且似乎可以扩大规模。

  DOI：

  10.1016/s0040-4020(03)00853-6
• 作为产物：
  描述：

  (1S,6S)-6-methyl-3-cyclohexene-1-carboxylic acid 在 potassium triiodide 、 偶氮二异丁腈 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 苯 为溶剂， 生成 (1RS,2RS,5RS)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  改进的顺式-5-碘-反式-2-甲基环己烷甲酸乙酯的合成，地中海果蝇的强力引诱剂

  摘要：

  由商业上可得到的外消旋反式方便地合成了外消旋的5-碘-2-甲基环己烷甲酸乙酯（1）（称为地中海果蝇引诱剂B 1）及其（-）-（1 R，2 R，5 R）对映体1a -6-甲基-3-环己烯羧酸2或其（1 R，6 R）对映异构体2a。关键步骤包括使用磺胺助剂进行不对称Diels-Alder反应，以及将不需要的反式-5-碘-反式-2-甲基环己烷羧酸环化（8）至中间体内酯7（或8a至7a）。新方法可能会绕过色谱分离，并且似乎可以扩大规模。

  DOI：

  10.1016/s0040-4020(03)00853-6

文献信息

• Regioselective synthesis of ceralure B1 and A, ethyl cis-(and trans-) 5-iodo-trans-2-methylcyclohexane-1-carboxylate
  作者：James W. Avery、Roy T. Cunningham、Rolland M. Waters

  DOI：10.1016/s0040-4039(00)78536-4

  日期：1994.12

  Reaction of trans-2-methyl-6-oxabicyclo[3.2.1]octan-7-one with trimethylsilyl iodide, generated in situ, followed by refluxing with ethanol gives regioselectively ethyl cis-(and trans-) 5-iodo-2-methylcyclohexane-1-carboxylate, a persistent attractant for male Mediterranean fruit flies.

  的反应反式-2-甲基-6-氧杂二环[3.2.1]辛-7-酮与三甲基碘硅烷，在原位产生的，随后用乙醇回流给出区域选择性乙基顺式- （和反式- ）5-碘-2-甲基环己烷-1-甲酸甲酯，是地中海雄性果蝇的持久引诱剂。
• Cyclohexanol ethers as mediterranean fruit fly attractants
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US10343974B1

  公开（公告）日：2019-07-09

  Disclosed are novel cyclohexanol ethers of Formula (I) useful as Mediterranean fruit fly, Ceratitas capitata, attractants: wherein R1 is C1-5 alkyl optionally substituted with 0-3 halogens, and R2 is C1-3 alkyl. Also disclosed are methods of preparation, methods of formulation, and methods of use.

  披露了作为地中海果蝇（Ceratitis capitata）引诱剂有用的新型环己醇醚的化学式（I），其中R1是C1-5烷基，可选地取代0-3个卤素，R2是C1-3烷基。还披露了制备方法、配方方法和使用方法。
• Method for the synthesis of ceralure B1
  申请人：The United States of America as represented by the Secretary of Agriculture

  公开号：US06777573B1

  公开（公告）日：2004-08-17

  A method has been developed for the preparation of ceralure B1, a potent attractant for the Mediterranean fruit fly. The method utilizes trans-siglure acid as starting material to produce iodolactone which is subsequently reduced to lactone. The lactone is converted to a mixture of epimers ceralure A acid and ceralure B1 acid. The ceralure A acid is recyclized to lactone, leaving epimer ceralure B1 acid intact. Following separation from lactone, the ceralure B1 acid is esterified to produce ceralure B1 of about 92-94% purity. The overall yield is about 58-65%, a significant improvement over currently known methods which result in yields of about 30-33%.

  已开发出一种制备地中海果蝇强效引诱剂Ceralure B1的方法。该方法利用顺式半萜酸作为起始物质，制备碘内酯，随后还原为内酯。内酯转化为混合外消旋体Ceralure A酸和Ceralure B1酸。Ceralure A酸回收重环化为内酯，使外消旋体Ceralure B1酸保持不变。从内酯中分离后，Ceralure B1酸酯化，制备出约92-94％纯度的Ceralure B1。总收率约为58-65％，明显优于目前已知的方法，其产率约为30-33％。
• Attractant for the mediterranean fruit fly, the method of preparation and method of use
  申请人：The United States of America as represented by the Secretary of Agriculture

  公开号：US06375943B1

  公开（公告）日：2002-04-23

  A method of attracting the Mediterranean fruit fly by subjecting the Mediterranean fruit fly to an attractant, wherein the attractant is ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1. The compound ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate, in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1, may be stereoselectively synthesized on a multigram scale in 15% yield by reacting ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate with Ph3P-imidazole-I2 (or Ph3P-2,6-lutidine-I2) in a carbon tetrachloride/methlylene chloride mixture. The 1R,2R,5R enantiomer is significantly more attractive than its enantiomeric counterpart (1S,2S,5S), or either of the commercial products trimedlure or ceralure, each a mixture of 16 regio and stereoisomers.

  一种通过将地中海果蝇置于诱 attract 剂下来吸引地中海果蝇的方法，其中诱 attract 剂是具有至少70％的对映异构体过量和>5:1的区域和立体化学纯度的乙酸乙酯基(1R,2R,5R)-5-碘-2-甲基环己烷-1-羧酸酯。该化合物可以在碳四氯/甲基氯混合物中通过将乙酸乙酯基(1R,2R,5S)-5-羟基-2-甲基-1-羧酸酯与Ph3P-咪唑-I2（或Ph3P-2,6-茚三醇-I2）反应，在至少70％的对映异构体过量和>5:1的区域和立体化学纯度下，以15％的产率进行立体选择性合成。1R、2R、5R对映异构体比其对映异构体（1S、2S、5S）或混合了16个区域和立体异构体的商业产品trimedlure或ceralure显着更具吸引力。
• Enantioselective Synthesis of Ceralure B1, Ethyl cis-5-Iodo-trans-2-methylcyclohexane-1-carboxylate
  作者：Andre S. Raw、Eric B. Jang

  DOI：10.1016/s0040-4020(00)00219-2

  日期：2000.5

  Ethyl (1R, 2R, SR)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. Published by Elsevier Science Ltd.