bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) cyclohex-4-ene-1,2-dicarboxylate | 189683-61-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) cyclohex-4-ene-1,2-dicarboxylate
• 英文别名: Di-(+)-menthyl cyclohex-4-ene-1,2-dicarboxylate；dimenthyl trans-cyclohex-4-ene-1,2-dicarboxylate
• CAS: 189683-61-2
• 化学式: C₂₈H₄₆O₄
• 分子量: 446.671
• InChiKey: BMHBKFSHTWSLPW-DJZRDOAWSA-N

物化性质

• 沸点：
  510.6±50.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) cyclohex-4-ene-1,2-dicarboxylate 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 苯 为溶剂， 反应 14.0h， 生成 (-)-(1R,2R)-1,2-O-Benzylidenecyclohex-4-ene-1,2-dimethanol
  参考文献：
  名称：

  Enantioselective synthesis of (+)-brefeldin A

  摘要：

  A new enantioselective synthesis of (+)-brefeldin A is described. The five chiral centers are created by the following methodology: asymmetric Diels-Alder reaction to prepare the cyclopentanone 13, stereocontrolled reduction of the carbonyl in the ketone 14, stereocontrolled creation of the chiral centers C-4 and C-15 by a chiral sulfoxide group.

  DOI：

  10.1021/jo00069a013
• 作为产物：
  描述：

  di-L-menthyl fumarate 、 1,3-丁二烯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) cyclohex-4-ene-1,2-dicarboxylate
  参考文献：
  名称：

  Asymmetric Diels-Alder reaction of 1,3-butadienes with (−)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt2

  摘要：

  Asymmetric synthesis of substituted cyclohexenes was performed by [4+2]-cycloaddition of (-)-dimenthyl fumarate to 1,3-butadienes in the presence of BBr3 and BBr3 center dot OEt2. The latter are efficient catalysts for this reaction. The effect of various factors on the chemical and optical yield of compounds synthesized was studied. The lowering of the reaction temperature to -70 degrees C favors increase in the enantiomeric purity of products C up to 81%. The overall yield of adducts grows with temperature and catalyst amount. The solvent character insignificantly affects the overall and optical yield of compounds obtained.

  DOI：

  10.1134/s1070428007020054

文献信息

• Synthesis and in vivo evaluation of 3,4-disubstituted gababutins
  作者：David C. Blakemore、Justin S. Bryans、Pauline Carnell、Mark J. Field、Natasha Kinsella、Jack K. Kinsora、Leonard T. Meltzer、Simon A. Osborne、Lisa R. Thompson、Sophie C. Williams

  DOI：10.1016/j.bmcl.2009.10.121

  日期：2010.1

  A range of 3,4-alkylated five-membered ring derivatives of gabapentin were synthesised. One compound (21) had an excellent level of potency against alpha(2)delta and was pro. led in in vivo models of pain and anxiety. (c) 2009 Elsevier Ltd. All rights reserved.