(R)-(-)-Heptyn-2-ol | 90192-97-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(-)-Heptyn-2-ol
• 英文别名: (R)-hept-4-yn-2-ol；(2R)-hept-4-yn-2-ol
• CAS: 90192-97-5
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: CXVIEBMEWKSONY-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-Heptyn-2-ol 在 正丁基锂 、 potassium tert-butylate 、 lithium 、 1,3-丙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (R)-7-(trimethylsilyl)hept-6-yn-2-ol
  参考文献：
  名称：

  (+)-Aspergillide B 和 (+)-7-epi-Aspergillide A 的立体发散全合成

  摘要：

  实现了(+)-曲霉内酯B和(+)-7-epi-曲霉内酯A的立体选择性全合成。关键反应包括 Noyori 的不对称转移氢化、Achmatowicz 重排、Ferrier 型炔基化、氢化硅烷化-原脱甲硅烷化、CBS（Corey-Bakshi-Shibata）氧杂硼烷还原、Yamaguchi 大内酯化和 Mitsunobu 大内酯化。

  DOI：

  10.1002/ejoc.201201155
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以66%的产率得到(R)-(-)-Heptyn-2-ol
  参考文献：
  名称：

  Stereoconvergent synthesis of the C1–C11 and C12–C24 fragments of (−)-macrolactin-A

  摘要：

  Stereoconvergent syntheses of the C1-C11 and C12-C24 fragments of (-)-macrolactin-A are reported. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.11.107

文献信息

• Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A
  作者：Heiko Sommer、Alois Fürstner

  DOI：10.1021/acs.orglett.6b01431

  日期：2016.7.1

  Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates

  当在CO气氛中，在MeOH中用催化量的Pd（OAc）2和Ph 3 As催化处理时，带有羟基侧基的烯基锡衍生物会经历甲氧基羰基化。成功的关键是将1,4-苯醌作为化学计量的氧化剂与三氟乙酸的助催化剂结合使用。酸降低了醌的LUMO，并可能封送了底物的关键组装。在优化的条件下，原型竞争是微不足道的；该方法被证明与各种（酸敏感）官能团兼容，并被用于抗生素tubelactomicin A的短时正式全合成。
• Synthesis and biological evaluation of 12-, 13-, 14-membered macrolides and open chain 2,6-trans-disubstituted dihydropyran analogues for aspergillides
  作者：Srihari Pabbaraja、Naresh Gantasala、Sridhar Ydhyam、Hari Krishna Namballa、Subhashini Gundeboina、Mallikharjuna R. Lambu、Sanjeev Meena、Dipak Datta

  DOI：10.1016/j.tetlet.2018.05.056

  日期：2018.6

  Stereoselective synthesis of twenty (three 12-, five 13- and twelve 14-membered) macrolides and seventeen functionalized 2,6-trans-disubstituted dihydropyran derivatives have been achieved. The key reactions include an Achmatowicz rearrangement, Ferrier-type alkynylation, Yamaguchi macrolactonization and Lindlar’s hydrogenation. Biological screening of the synthesised compounds showed moderate activity

  已经实现了二十（三十二，五十三和十二十四个十四元）大环内酯和十七个官能化的2，6-反式-二取代的二氢吡喃衍生物的立体选择性合成。关键反应包括Achmatowicz重排，Ferrier型炔基化，Yamaguchi大内酯化和Lindlar加氢。合成化合物的生物学筛选显示出对人癌细胞系的中等活性。
• Stereodivergent Total Synthesis of (+)-Aspergillide B and (+)-7-<i>epi</i>-Aspergillide A
  作者：Y. Sridhar、P. Srihari

  DOI：10.1002/ejoc.201201155

  日期：2013.1

  The stereoselective total syntheses of (+)-aspergillide B and (+)-7-epi-aspergillide A were achieved. The key reactions include Noyori's asymmetric transfer hydrogenation, an Achmatowicz rearrangement, a Ferrier-type alkynylation, a hydrosilylation–protodesilylation, a CBS (Corey–Bakshi–Shibata) oxazaborolidine reduction, a Yamaguchi macrolactonization, and a Mitsunobu macrolactonization.

  实现了(+)-曲霉内酯B和(+)-7-epi-曲霉内酯A的立体选择性全合成。关键反应包括 Noyori 的不对称转移氢化、Achmatowicz 重排、Ferrier 型炔基化、氢化硅烷化-原脱甲硅烷化、CBS（Corey-Bakshi-Shibata）氧杂硼烷还原、Yamaguchi 大内酯化和 Mitsunobu 大内酯化。
• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.
• Synthesis of Z,Z-skipped diene macrolide pheromones for Cryptolestes and Oryzaephilus grain beetles (Coleoptera Cucujidae)
  作者：Jocelyn G. Millar、Allan C. Oehlschlager

  DOI：10.1021/jo00187a007

  日期：1984.6