(1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid | 102629-35-6

• 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,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid
• 英文别名: (1R,6S)-6-methyl-3-cyclohexenecarboxylic acid；(-)-(1R,2S)-1-carboxy-2-methyl-4-cyclohexene；cis-6-Methyl-cyclohex-3-en-1-carbonsaeure；(1R,6S)-6-Methylcyclohex-3-ene-1-carboxylic acid
• CAS: 102629-35-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: UTEIUSUWIZICDO-NKWVEPMBSA-N

物化性质

• 沸点：
  246.0±19.0 °C(Predicted)
• 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：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid 在 咪唑 、 lithium aluminium tetrahydride 、 碘 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 112.0h， 生成 (4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  通过化学酶促方法对环己烯酮衍生物的对映选择性合成：立体和区域选择性途径，生成紧密蛋白（ML 236B）和美维林的潜在中间体。

  摘要：

  作为手性单酯2的合成应用，研究了通过猪肝酯酶（PLE）催化水解相应的内消旋二酯1制备的手性单酯2，将2转化为各种环己烯酮衍生物。本文描述了异构体环己烯酮6和7的制备方法，这些化合物是在立体和区域选择性控制下合成抗高胆固醇紧缩蛋白（ML 236B）和美维诺林的潜在中间体。

  DOI：

  10.1248/cpb.38.1479
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 偶氮二异丁腈 、 氢溴酸 、 三正丁基氢锡 作用下， 以 正己烷 、 水 为溶剂， 反应 31.0h， 生成 (1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid
  参考文献：
  名称：

  Enzymes in organic synthesis 49. Resolutions of racemic monocyclic esters with pig liver esterase.

  摘要：

  Pig liver esterase (PLE)- catalyzed hydrolyses of the racemic methyl esters of cyclobutane-, cyclohexane-, and cyclohex-4-ene-carboxylic acids bearing cis-2-methyl or cis-2-bromomethyl substituents are highly stereoselective, giving the corresponding acid products of greater-than-or-equal-to 97% ee. The stereoselectivity of the enzyme exhibits the expected reversal for such compounds, with the absolute configurations of the cyclobutane and cyclohexane acids being of the opposite absolute configuration types, and cyclopentane substrates such as cis-1-carbomethoxy-2-methylcyclopentane representing the change-over structures and giving products of only 22% ee. This stereoselectivity reversal, and the absolute configurations preferred, are as predicted by the recently proposed active site model for the enzyme.

  DOI：

  10.1016/s0957-4166(00)82360-5

文献信息

• Synthetic studies related to compactin: use of tri-O-acetyl-D-glucal for preparation of chiral cyclohexenes
  作者：J. Siva Prasad、Derrick L. J. Clive、Gil V. J. Da Silva

  DOI：10.1021/jo00364a018

  日期：1986.7
• MCGOVERN, TERRENCE P.;CUNNINGHAM, ROY T.
  作者：MCGOVERN, TERRENCE P.、CUNNINGHAM, ROY T.

  DOI：——

  日期：——
• KOBAYASHI, SUSUMU;EGUCHI, YOSHIHITO;SHIMADA, MITSUYUKI;OHNO, MASAJI, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1479-1484
  作者：KOBAYASHI, SUSUMU、EGUCHI, YOSHIHITO、SHIMADA, MITSUYUKI、OHNO, MASAJI

  DOI：——

  日期：——
• Enzymes in organic synthesis 49. Resolutions of racemic monocyclic esters with pig liver esterase.
  作者：Eric J. Toone、J.Bryan Jones

  DOI：10.1016/s0957-4166(00)82360-5

  日期：1991.1

  Pig liver esterase (PLE)- catalyzed hydrolyses of the racemic methyl esters of cyclobutane-, cyclohexane-, and cyclohex-4-ene-carboxylic acids bearing cis-2-methyl or cis-2-bromomethyl substituents are highly stereoselective, giving the corresponding acid products of greater-than-or-equal-to 97% ee. The stereoselectivity of the enzyme exhibits the expected reversal for such compounds, with the absolute configurations of the cyclobutane and cyclohexane acids being of the opposite absolute configuration types, and cyclopentane substrates such as cis-1-carbomethoxy-2-methylcyclopentane representing the change-over structures and giving products of only 22% ee. This stereoselectivity reversal, and the absolute configurations preferred, are as predicted by the recently proposed active site model for the enzyme.
• Enantioselective synthesis of cyclohexenone derivatives by a chemicoenzymatic approach: Stereo- and regioselective route to potential intermediates of compactin (ML 236B) and mevinolin.
  作者：Susumu KOBAYASHI、Yoshihito EGUCHI、Mitsuyuki SHIMADA、Masaji OHNO

  DOI：10.1248/cpb.38.1479

  日期：——

  of 2 into various cyclohexenone derivatives was examined. This paper describes the preparation of the isomeric cyclohexenones 6 and 7, potential intermediates for the synthesis of anti-hypercholesmic compactin (ML 236B) and mevinolin, under stereo- and regioselective control.

  作为手性单酯2的合成应用，研究了通过猪肝酯酶（PLE）催化水解相应的内消旋二酯1制备的手性单酯2，将2转化为各种环己烯酮衍生物。本文描述了异构体环己烯酮6和7的制备方法，这些化合物是在立体和区域选择性控制下合成抗高胆固醇紧缩蛋白（ML 236B）和美维诺林的潜在中间体。