((1S,2S)-2-Hydroxy-cyclohexyl)-acetic acid methyl ester | 145107-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1S,2S)-2-Hydroxy-cyclohexyl)-acetic acid methyl ester
• 英文别名: Methyl [(1S,2S)-2-hydroxycyclohexyl]acetate；methyl 2-[(1S,2S)-2-hydroxycyclohexyl]acetate
• CAS: 145107-54-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: TXZRYAJZEVSREG-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  ((1S,2S)-2-Hydroxy-cyclohexyl)-acetic acid methyl ester 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 生成 (3aS,7aS)-hexahydrobenzofuran-2(3H)-one
  参考文献：
  名称：

  面包酵母还原烷基（2-氧代环己基）乙酸酯。

  摘要：

  贝克酵母还原乙酸甲酯和乙酸乙酯（2-氧代环己基）的对映体和非对映体选择性，得到相应的（2S）-反式醇（主要），（2S）-顺式醇（次要）和未改变的具有高光学纯度的（1S）-酮。

  DOI：

  10.1271/bbb.62.181
• 作为产物：
  描述：

  (2-氧代环己基)-乙酸甲酯 在 盐酸 、 silver tetrafluoroborate 、 (S,S)-2,6-双(4-异丙基-2-恶唑啉-2-基)吡啶 、 (ip-pybox)RhCl₃ 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 ((1S,2S)-2-Hydroxy-cyclohexyl)-acetic acid methyl ester
  参考文献：
  名称：

  Stereoselectivity in hydrosilylative reduction of substituted cyclohexanone derivatives with chiral rhodium-bis(oxazolinyl)pyridine catalyst

  摘要：

  Stereoselectivity in the reduction of substituted cyclohexanones, 4-tert-butylcycohexanone, 2-methylcycohexanone, 2-phenylcyclohexanone, and 2-methoxycarbonyl-methylcyclohexanone, was examined with chiral rhodium-bis(oxazolinyl)pyridine catalyst and diphenylsilane. 4-tert-Butylcyclohexanone gave the corresponding trans(equatorial)-alcohol predominantly; the ratio of the trans/cis alcohols, 67:33. Other 2-substituted cyclohexanones showed exclusive enantioselectivities for each diastereomer in terms of the kinetic resolution; e.g. from 2-phenylcyclohexanone, 99 % ee of (1S, 2R)-trans-2-phenylcyclohexanol and 96 % ee of (1S, 2S)-cis-2-phenylcyclohexanol in 92 % yield (the trans/cis ratio = 51:49).

  DOI：

  10.1016/s0957-4166(00)86036-x

文献信息

• Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases
  作者：Nikolaus G. Turrini、Răzvan C. Cioc、Daan J. H. van der Niet、Eelco Ruijter、Romano V. A. Orru、Mélanie Hall、Kurt Faber

  DOI：10.1039/c6gc02493a

  日期：——

  The asymmetric bioreduction of [small alpha],[small beta]-unsaturated [gamma]-keto esters using ene-reductases from the Old Yellow Enzyme family proceeds with excellent stereoselectivity and high conversion levels, covering a broad range of acyclic and...

  使用Old Yellow Enzyme家族的烯键还原酶对小，小β-不饱和γ-酮酸酯进行不对称生物还原，具有出色的立体选择性和高转化率，涵盖了广泛的无环和...
• Syntheses of (+)- and (−)-Dihydropinidine and (+)- and (−)-Epidihydropinidine by Using Yeast Reduction of Methyl (2-oxocyclohexyl)acetate
  作者：Satoshi YAMAUCHI、Shunji MORI、Yoshio HIRAI、Yoshiro KINOSHITA

  DOI：10.1271/bbb.68.676

  日期：2004.1

  (+) and (−)-Dihydropinidine and (+)- and (−)-epidihydropinidine were synthesized from hydroxy esters 1 and 2 which had been prepared by yeast reduction of methyl (2-oxocyclohexyl)acetate. The enantiomeric excess at the C-1 positions of 1 and 2 were both determined as more than 99% ee.

  (+)和(-)-二氢吡啶以及(+)和(-)-表二氢吡啶是由羟基酯 1 和 2 合成的，羟基酯 1 和 2 是通过酵母还原 (2-oxocyclohexyl)acetate 甲酯制备的。经测定，1 和 2 的 C-1 位对映体过量率均超过 99%ee。
• Stereoselectivity in hydrosilylative reduction of substituted cyclohexanone derivatives with chiral rhodium-bis(oxazolinyl)pyridine catalyst
  作者：Hisao Nishiyama、Soon-Bong Park、Kenji Itoh

  DOI：10.1016/s0957-4166(00)86036-x

  日期：1992.8

  Stereoselectivity in the reduction of substituted cyclohexanones, 4-tert-butylcycohexanone, 2-methylcycohexanone, 2-phenylcyclohexanone, and 2-methoxycarbonyl-methylcyclohexanone, was examined with chiral rhodium-bis(oxazolinyl)pyridine catalyst and diphenylsilane. 4-tert-Butylcyclohexanone gave the corresponding trans(equatorial)-alcohol predominantly; the ratio of the trans/cis alcohols, 67:33. Other 2-substituted cyclohexanones showed exclusive enantioselectivities for each diastereomer in terms of the kinetic resolution; e.g. from 2-phenylcyclohexanone, 99 % ee of (1S, 2R)-trans-2-phenylcyclohexanol and 96 % ee of (1S, 2S)-cis-2-phenylcyclohexanol in 92 % yield (the trans/cis ratio = 51:49).
• Reduction of Alkyl (2-Oxocyclohexyl)acetates by Baker’s Yeast
  作者：Makoto GANAHA、Yuhei FUNABIKI、Minoru MOTOKI、Satoshi YAMAUCHI、Yoshiro KINOSHITA

  DOI：10.1271/bbb.62.181

  日期：1998.1

  Baker's yeast reduction of methyl and ethyl (2-oxocyclohexyl) acetates proceeded with enantio- and diastereo-selectivity, affording the corresponding (2S)-trans-alcohols (major), (2S)-cis-alcohols (minor), and the unaltered (1S)-ketones with high optical purity.

  贝克酵母还原乙酸甲酯和乙酸乙酯（2-氧代环己基）的对映体和非对映体选择性，得到相应的（2S）-反式醇（主要），（2S）-顺式醇（次要）和未改变的具有高光学纯度的（1S）-酮。