ethyl (1R,2R)-2-methyl-5-one-1-carboxylate | 287178-36-3

• 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: ethyl (1R,2R)-2-methyl-5-one-1-carboxylate
• 英文别名: Ethyl (1R,2R)-2-methylcyclohexane-5-one1-carboxylate；ethyl (1R,2R)-2-methyl-5-oxocyclohexane-1-carboxylate
• CAS: 287178-36-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NFYIJYQWAIPFAL-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2R)-2-methyl-5-one-1-carboxylate 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到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
• 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 、 pyridinium chlorochromate 、 potassium iodide 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 25.0h， 生成 ethyl (1R,2R)-2-methyl-5-one-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.

  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。
• US6375943B1
  申请人：——

  公开号：US6375943B1

  公开（公告）日：2002-04-23
• 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.