(R)-6-hepten-2-ol acetate | 852065-86-2

• 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: (R)-6-hepten-2-ol acetate
• 英文别名: (2R)-2-acetoxy-6-heptene；(R)-2-acetoxyhept-6-ene；[(2R)-hept-6-en-2-yl] acetate
• CAS: 852065-86-2
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: YSVUPNHQXJSBTC-MRVPVSSYSA-N

物化性质

• 沸点：
  196.7±19.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (R)-6-hepten-2-ol acetate 在 甲醇 、 氢氧化钾 作用下， 反应 6.0h， 以88%的产率得到(R)-6-hepten-2-ol
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella

  摘要：

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.004
• 作为产物：
  描述：

  庚-6-烯-2-醇 、 乙酸异丙烯酯 在 Candida antarctica lipase B 、 sodium carbonate 作用下， 以 正戊烷 为溶剂， 反应 4.0h， 以50%的产率得到(R)-6-hepten-2-ol acetate
  参考文献：
  名称：

  酶和钌催化的1，5-二元醇动态动力学不对称转化。在合成（+）-Soloopsin A中的应用

  摘要：

  通过组合的脂肪酶和钌催化作用的1,5-二醇动态动力学不对称转化（DYKAT）提供了对映体纯的二乙酸酯，具有高非对映选择性，可以用作天然产物合成的中间体。（+）-Solenopsin A的合成证明了这一点。

  DOI：

  10.1021/jo8025109

文献信息

• PdII-Catalyzed stereospecific formation of tetrahydro- and 3,6-dihydro[2H]pyran rings: 1,3-chirality transfer by intramolecular oxypalladation reaction
  作者：Jun’ichi Uenishi、Masashi Ohmi、Atsushi Ueda

  DOI：10.1016/j.tetasy.2005.02.006

  日期：2005.4

  The stereospecific synthesis of 2,6-disubstituted tetrahydropyran and 3,6-dihydro[2H]pyran is described. The PdII-catalyzed cyclization of the hydroxy nucleophile to the allylic alcohol takes place efficiently under mild conditions, with the stereogenic center on the secondary allylic alcohol transfers to a newly generated stereogenic center on pyran ring via a syn-SN2′ type process.

  描述了2,6-二取代的四氢吡喃和3,6-二氢[2 H ]吡喃的立体有择合成。在温和条件下，Pd II催化的羟基亲核试剂向烯丙基醇的环化反应有效发生，仲烯丙基醇上的立体生成中心通过syn -S N 2'型过程转移至吡喃环上新生成的立体生成中心。。
• FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans
  作者：Amandine Guérinot、Anna Serra-Muns、Christian Gnamm、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1021/ol100422d

  日期：2010.4.16

  The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.
• FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives
  作者：Amandine Guérinot、Anna Serra-Muns、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tet.2011.03.112

  日期：2011.7

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and stereochemical assignment of (+)-Cladospolide D
  作者：Ke-Jhen Lu、Chia-Hsiu Chen、Duen-Ren Hou

  DOI：10.1016/j.tet.2008.10.059

  日期：2009.1

  Cladospolides A-D are 12-membered, alpha,beta-unsaturated lactones isolated from various species of Cladosporium. Cladospolide D is unique in its gamma-keto functionality and possesses antifungal activity; however, the stereochemistry of Cladoapolide D was unknown. We report the asymmetric syntheses to generate both possible diastereomers of Cladospolide D. Two regioselective cross-metatheses were applied to form the carbon skeleton, and the two olefins were differentiated by Michael addition, hydrogenation, and elimination. Later, the macrocycle was achieved through the Yamaguchi protocol. After comparing the spectroscopic data of the synthetic Cladospolide D with the reported values, the stereochemistry of Cladospolide D is confirmed as (2E,5R,11S). (C) 2008 Elsevier Ltd. All rights reserved.