ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate | 287178-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate
• 英文别名: ethyl (1R,2R,5S)-5-hydroxy-2-methylcyclohexane-1-carboxylate
• CAS: 287178-38-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: GUPQXDHWDBBGNX-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 以53%的产率得到ceralure B1
  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-3-cyclohexenecarboxylic acid 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 sodium ethanolate 、 碳酸氢钠 、 potassium tri-sec-butyl-borohydride 、 pyridinium chlorochromate 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 29.0h， 生成 ethyl (1R,2R,5S)-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

文献信息

• 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.