[(1R,2S)-2-(hydroxymethyl)cyclohexyl]methyl acetate | 98516-09-7

• 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,2S)-2-(hydroxymethyl)cyclohexyl]methyl acetate
• CAS: 98516-09-7
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: SAQOPXMHRBZRJI-ZJUUUORDSA-N

物化性质

• 沸点：
  267.5±13.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 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：

  [(1R,2S)-2-(hydroxymethyl)cyclohexyl]methyl acetate 在 重铬酸吡啶 、 hydroxide 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 hexahydro-isobenzo[c]furan-1-one
  参考文献：
  名称：

  酶酯的水解和合成-高对映体纯度的环烷烃衍生物的两种方法

  摘要：

  （1 ，2 ） -和（1 ，2 ）-Acetoxycycloalkanedimethanols 1-6高对映体纯度的被酶水解和酯化分别在从猪胰腺（PPL）和脂肪酶的存在下制备的假单孢菌。（SAM-II）。

  DOI：

  10.1016/s0040-4039(00)99581-9
• 作为产物：
  描述：

  cis-1,2-cyclohexanedimethanol diacetate 以54%的产率得到
  参考文献：
  名称：

  ADER, ULRICH;BREITGOFF, DETLEF;KLEIN, PETER;LAUMEN, KURT E.;SCHNEIDER, MA+, TETRAHEDRON LETT., 30,(1989) N4, C. 1793-1796

  摘要：

  DOI：

文献信息

• Asymmetric ring cleavage reaction based on crossed aldol condensation
  作者：Hiroshi Suemune、Osamu Yoshida、Jun Uchida、Yukiko Nomura、Masakazu Tanaka、Kiyoshi Sakai

  DOI：10.1016/0040-4039(95)01504-b

  日期：1995.10

  Ring cleavage reaction based on crossed aldol condensation of carbobicyclic ketones with benzaldehyde under acetalization conditions (BF3·Et2O/ethylene glycol) was studied. By using optically active 1,2-diols instead of ethylene glycol, an asymmetric version of this reaction could be developed for the first time.

  研究了在缩醛化条件下（BF 3 ·Et 2 O /乙二醇）基于碳双环酮与苯甲醛的交叉羟醛缩合反应的开环反应。通过使用旋光的1,2-二醇代替乙二醇，可以首次开发出该反应的不对称形式。
• Preparation of chiral hydroxyester synthons vis stereoselective porcine pancreatic lipase-catalysed hydrolyses of meso-diesters
  作者：Wolfgang Kasel、Philip G. Hultin、J. Bryan Jones

  DOI：10.1039/c39850001563

  日期：——

  Stereoselective porcine pancreatic lipase-catalysed hydrolyses of monocyclic meso-1,2-diesters provides a flexible and convenient preparative route to chiral hydroxyesters and lactones of asymmetric synthetic value.

  立体选择性猪胰腺脂肪酶催化的单环内消旋-1，2-二酯水解为制备具有不对称合成价值的手性羟基酯和内酯提供了一种灵活方便的制备途径。
• Bhattacharya, A; Ali, E, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 898 - 899
  作者：Bhattacharya, A、Ali, E

  DOI：——

  日期：——
• Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols
  作者：Alexandra N. E. Weissfloch、Romas J. Kazlauskas

  DOI：10.1021/jo00126a056

  日期：1995.10

  We propose an empirical rule that predicts which enantiomer of a primary alcohol reacts faster in reactions catalyzed by lipase from Pseudomonas cepacia (PCL). This rule, based on the size of the substituents at the stereocenter, shows an 89% reliability (correct for 54 of 61 examples). This rule is not reliable for primary alcohols that have an oxygen atom attached to the stereocenter; we excluded these alcohols from the tally above. Surprisingly, the sense of enantiopreference of PCL toward primary alcohols is opposite to its enantiopreference toward secondary alcohols. That is, the OH of secondary alcohols and the CH2OH of primary alcohols point in opposite directions. We suggest, however, that this opposite orientation does not imply a different position of the substituents in the active site of the lipase. Instead, PCL accommodates the extra CH2 in primary alcohols as a kink between the stereocenter and the oxygen which allows a similar position of the alcohol oxygen in both. We tried to increase the enantioselectivity of PCL toward primary alcohols by increasing the difference in the size of the substituents but did not find a consistent increase in enantioselectivity. We suggest that high enantioselectivity toward primary alcohols requires not only a significant difference in the size of the substituents, but also control of the conformation along the C(1)-C(2) bond.
• KASEL, W.;HULTIN, PH. G.;JONES, J. B., J. CHEM. SOC. CHEM. COMMUN., 1985, N 22, 1563-1564
  作者：KASEL, W.、HULTIN, PH. G.、JONES, J. B.

  DOI：——

  日期：——