(S)-6-methyl-5-hepten-2-yl acetate | 123284-88-8

• 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: (S)-6-methyl-5-hepten-2-yl acetate
• 英文别名: (S-)-(+)-sulcatol acetate；(S)-sulcatol acetate；S-sulcatol acetate；(1S)-1,5-Dimethyl-4-hexenyl acetate；[(2S)-6-methylhept-5-en-2-yl] acetate
• CAS: 123284-88-8
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: ZAKWGQOSOHQPJA-VIFPVBQESA-N

物化性质

• 沸点：
  178.3±9.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-6-methyl-5-hepten-2-yl acetate 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-(-)-6-甲基-5-烯基-2-戊醇
  参考文献：
  名称：

  High-speed microwave-promoted Mitsunobu inversions. Application toward the deracemization of sulcatol

  摘要：

  An enantioconvergent synthesis of the aggregation pheromones (R)- and (S)-suleatol (6-methyl-5-hepten-2-ol) is described. Key steps in the deracemization strategy are sequential combinations of enzymatic resolutions and Mitsunobu inversions. Racemization-free Mitsunobu transformations have been carried out within 5 min by microwave irradiation, providing the desired sulcatyl acetates with clean inversion of chirality. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01248-5
• 作为产物：
  描述：

  ethyl 2-(3-methyl-2-buten-1-yl)-3-oxobutanoate 在 吡啶 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (S)-6-methyl-5-hepten-2-yl acetate
  参考文献：
  名称：

  制备旋光性仲醇的有用方法：（）-和（）-磺胺醇的短对映体合成

  摘要：

  差向异构的2-（1-羟乙基）-5-甲基-4-己烯酸是通过面包酵母还原相应的羰基化合物或通过光学上纯的3-羟基丁酸酯的烷基化而制备的。自由基链脱羧得到舒丁醇的对映体。该方法可能广泛适用于其他光学纯醇的合成。

  DOI：

  10.1016/s0040-4039(00)99105-6

文献信息

• Convenient Enzymatic Resolution of Alcohols Using Highly Reactive, Nonharmful Acyl Donors, 1-Ethoxyvinyl Esters
  作者：Yasuyuki Kita、Yasushi Takebe、Kenji Murata、Tadaatsu Naka、Shuji Akai

  DOI：10.1021/jo9910785

  日期：2000.1.1

  1-Ethoxyvinyl esters 3, a new type of acyl donors for enzymatic resolution of racemic alcohols, were disclosed to be superior to the contemporary major reagents, vinyl esters 1 and isopropenyl esters 2. Three features of 3 are noticeable: (1) 3 generates ethyl acetate as a single coproduct, which does not affect any enzymes, while acetaldehyde liberated from 1 deactivates some kinds of lipases. (2)

  1-乙氧基乙烯基酯3是用于消旋外消旋醇酶促分解的一种新型酰基供体，其性能优于现代主要试剂乙烯基酯1和异丙烯基酯2。3的三个特征十分明显：（1）3生成乙酸乙酯为单一副产物，不影响任何酶，而从1释放的乙醛会使某些脂肪酶失活。（2）3的反应性不少于1，并且比2高得多，并且产物的光学纯度与1和2一样高。特别是，通常观察到3显示出更高的反应性。对于使用白色念珠菌脂肪酶（最常用的脂肪酶之一）的反应，其对底物的适应性较广，但对乙醛敏感，反应速率大于1。给出了十二个外消旋仲醇的动力学拆分实例（5和10）和一种中消元醇7的不对称化反应，其中使用了乙酸3a或辛酸3b和四种脂肪酶。（3）阐明了用一锅法从相应的羧酸制备3和随后的醇的酶促分解的方法，该方法尚未报道使用1或2。通过该程序得到的产品的化学和光学收率与分离得到的3相似。被阐明。通过该程序得到的产品的化学和光学收率与分离得到的3相似。被阐明。通过该程序得到
• Factors influencing enantioselectivity of lipase-catalyzed hydrolysis
  作者：Masamichi Kinoshita、Atsuyoshi Ohno

  DOI：10.1016/0040-4020(96)00179-2

  日期：1996.4

  Some factors influencing the enantioselectivity of lipase-catalyzed hydrolysis have been investigated. Enantioselectivity of the reaction increases with the increase in the concentration of substrate. Addition of certain organic solvent to the reaction mixture results in the change in enantioselectivity: hexane, cyclopentane, benzene and diisopropyl ether improve the enantioselectivity, whereas cyclohexane

  研究了一些影响脂肪酶催化水解的对映选择性的因素。反应的对映选择性随底物浓度的增加而增加。向反应混合物中添加某些有机溶剂会导致对映选择性的变化：己烷，环戊烷，苯和二异丙醚会提高对映选择性，而环己烷会使对映选择性恶化。在动力学相对于底物饱和的条件下，去污剂Triton X-100和2,2-二甲基丁烷不影响对映选择性。对映选择性的波动取决于疏水化合物与脂肪酶的结合。
• Structure of solvent affects enantioselectivity of lipase-catalyzed transesterification
  作者：Kaoru Nakamura、Masamichi Kinoshita、Atsuyoshi Ohno

  DOI：10.1016/0040-4020(95)00470-s

  日期：1995.8

  Lipase-catalyzed transesterification of (rac)-6-methyl-5-hepten-2-ol (sulcatol) with vinyl acetate has been studied in various solvents and the effect of solvent on the enantioselectivity has been discussed from the viewpoint of molecular shape of the solvent. Alkanes and ethers are selected as solvents. Enantioselectivity of a reaction in a structurally linear solvent is higher than that in the corresponding branched chain solvent. Furthermore, the enantioselectivity decreases specifically with the increase in the ring size of solvent molecule. Thus, lipase recognizes not only the structure of substrate but also that of solvent.
• Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure
  作者：Andreas Steinreiber、Klaus Edegger、Sandra F. Mayer、Kurt Faber

  DOI：10.1016/s0957-4166(01)00370-6

  日期：2001.8

  A short chemoenzymatic synthesis of the (2R,5S)- and (2R,5R)-stereoisomer of the bark beetle pheromone Pityol 1 was achieved from (+/-)-Sulcatol 2 in an enantio- and diastereo-convergent fashion without the formation of any 'unwanted' stereoisomer. The key steps include: (i) lipase-catalyzed deracemization of (+/-)-2 using kinetic resolution coupled to an in-situ inversion or alternatively, dynamic resolution using combined lipase- and Ru-catalysis: and (ii) creation of the second stereogenic center by an epoxide hydrolase-catalyzed diastereo-convergent hydrolysis of a haloalkyl oxirane, followed by spontaneous ring Closure to form 1 in a stereoselective fashion. (C) 2001 Published by Elsevier Science Ltd.
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  DOI：10.1016/s0957-4166(00)86349-1

  日期：1990.1