(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid | 10479-42-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid
• 英文别名: 3-Cyclohexene-1-carboxylic acid, 6-methyl-, (1R,6R)-rel-；(1R,6R)-6-methylcyclohex-3-ene-1-carboxylic acid
• CAS: 10479-42-2
• 化学式: C₈H₁₂O₂
• mdl: MFCD19228461
• 分子量: 140.182
• InChiKey: UTEIUSUWIZICDO-RNFRBKRXSA-N

物化性质

• 熔点：
  64-65 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  140 °C(Press: 20 Torr)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916209090

反应信息

• 作为反应物：
  描述：

  (-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 sodium ethanolate 、 碳酸氢钠 、 potassium iodide 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 25.0h， 生成 ethyl (1R,2R,5R)-5-hydroxy-2-methyl-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Ceralure B1, Ethyl cis-5-Iodo-trans-2-methylcyclohexane-1-carboxylate

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(00)00219-2
• 作为产物：
  描述：

  (1R,6R)-6-methyl-N-[(1R)-1-phenylethyl]cyclohex-3-ene-1-carboxamide 在 盐酸 、 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 jones reagent 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 (-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid
  参考文献：
  名称：

  Enantiomers of the biologically active components of the insect attractant trimedlure

  摘要：

  DOI：

  10.1021/jo00198a012

文献信息

• An improved synthesis of ethyl cis-5-iodo-trans-2-methylcyclohexanecarboxylate, a potent attractant for the Mediterranean fruit fly
  作者：Ashot Khrimian、Armenak Kh. Margaryan、Walter F. Schmidt

  DOI：10.1016/s0040-4020(03)00853-6

  日期：2003.7

  Both racemic ethyl 5-iodo-2-methylcyclohexanecarboxylate (1), known as Mediterranean fruit fly attractant ceralure B1, and its (−)-(1R,2R,5R) enantiomer 1a were conveniently synthesized from commercially available racemic trans-6-methyl-3-cyclohexenecarboxylic acid 2 or its (1R,6R) enantiomer 2a. Key steps included an asymmetric Diels–Alder reaction using a sultam auxiliary and cyclization of the unwanted

  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。
• 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。
• 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.

  通过将地中海果蝇暴露于一种引诱剂中来吸引地中海果蝇的方法，其中引诱剂是乙基(1R,2R,5R)-5-碘-2-甲基环己烷-1-羧酸乙酯，其对映体过量至少为70%，区域和立体化学纯度大于5:1。乙基(1R,2R,5R)-5-碘-2-甲基环己烷-1-羧酸乙酯化合物，在对映体过量至少为70%和区域和立体化学纯度大于5:1的情况下，可通过将乙基(1R,2R,5S)-5-羟基-2-甲基-1-羧酸乙酯与Ph3P-咪唑-碘（或Ph3P-2,6-吖啶-碘）在四氯化碳/甲基氯仿混合物中反应，在15%的产率下立体选择性地合成多克级规模的1R,2R,5R对映体。1R,2R,5R对映体比其对映体对应物（1S,2S,5S）或商业产品trimedlure或ceralure更具吸引力，trimedlure或ceralure是16个区域和立体异构体的混合物。
• 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％。
• Attractants for the Mediterranean fruit fly
  申请人：THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce

  公开号：EP0340971A2

  公开（公告）日：1989-11-08

  Novel attractants for the Mediterrean Fruit fly, "Medfly" comprise isomeric blends of Cl-C₅ alkyl esters of iodo-trans-2-methylcyclohexanecarboxylic acid.

  针对地中海果蝇的新型引诱剂由碘-反式-2-甲基环己烷羧酸的 Cl-C₅ 烷基酯异构体混合物组成。