(S)-(+)-5-hydroxyheptanol | 113611-50-0

• 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: (S)-(+)-5-hydroxyheptanol
• 英文别名: (5S)-heptane-1,5-diol
• CAS: 113611-50-0
• 化学式: C₇H₁₆O₂
• 分子量: 132.203
• InChiKey: NNYOSLMHXUVJJH-ZETCQYMHSA-N

物化性质

• 沸点：
  242.0±8.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-5-hydroxyheptanol 在 三乙烯二胺 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-(-)-5-fluoroheptyl benzoate
  参考文献：
  名称：

  Synthesis and Properties of Ferroelectric Liquid Crystals Derived from 5-Alkyl-δ-Valerolactones

  摘要：

  New homologous FLCs (I similar to II-n [n=1 similar to4]) derived from optically active 5-alkyl-6-valerolactones were synthesized. Their mesomorphic properties were systematically investigated with respect to their molecular structures, which were different in terms of the length of an alkyl group attached to a chiral centre and the direction of phenylpyrimidyl group. For compounds type I-n, with pyrimidyl group conjugated to the terminal position carrying chiral 5-fluoro-alkyloxy tail, elongation of the attached alkyl groups enhanced the stability of the chiral smectic C phase, while the other type, with pyrimidyl group conjugated to the terminal position carrying achiral alkyloxy tail, showed no remarkable alteration in the stability of the phase. Short optical response time (22 mus, 80 degreesC[Tc-T=10K]) was found for the FLC II-3 that has almost the same magnitude of spontaneous polarization (25nCcm(-2), 80 degreesC[Tc-T=10K]) with that of 11-4.

  DOI：

  10.1080/10587250008023865
• 作为产物：
  描述：

  2H-吡喃-2-酮,6-乙基四氢-,(S)- 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(+)-5-hydroxyheptanol
  参考文献：
  名称：

  Optical Resolution of 5-Alkyl-δ-Valerolactones and Synthesis of Optically Active 5-Fluoroalkanols

  摘要：

  Optical resolutions of 5-alkyl-delta-valerolactones were carried out by derivatization to the diastereomeric amides, in which (R)-(+)1-(1-naphthyl)ethylamine or (S)-(-)-1-phenylethylamine were used as resolving agents. Optically active 5-fluoroalkanols, useful intermediates for fluorinated ferroelectric liquid crystals, were derived from the resolved lactones in four steps without racemization.

  DOI：

  10.1080/10242430210707

文献信息

• Enzymatic kinetic resolution of internal propargylic diols. Part I: a new approach for the synthesis of (S)-pent-2-yn-1,4-diol, a natural product from Clitocybe catinus
  作者：Jeiely G. Ferreira、Cleverson R. Princival、Dyego M. Oliveira、Renata X. Nascimento、Jefferson L. Princival

  DOI：10.1039/c5ob00386e

  日期：——

  Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.

  内部双取代的炔丙基二醇经过CAL-B促进的酶动力学拆分。使用两轮序列EKR，以高对映体比率（E > 200）获得单乙酰基和双乙酰氧基炔丙基产物。有效拆分手性8b应用于（S）-1b的简明合成中，这是一种由真菌Clitocybe catinus生产的光学活性天然产物。
• Synthesis and Biological Properties of Novel Brefeldin A Analogues
  作者：Kai Seehafer、Frank Rominger、Günter Helmchen、Markus Langhans、David G. Robinson、Başak Özata、Britta Brügger、Jeroen R. P. M. Strating、Frank J. M. van Kuppeveld、Christian D. Klein

  DOI：10.1021/jm400615g

  日期：2013.7.25

  New brefeldin A (1) analogues were obtained by introducing a variety of substituents at C15. Most of the analogues exhibited significant biological activity. (15R)-Trifluoromethyl-nor-brefeldin A (3), (15R)-vinyl-nor-brefeldin A (5), their epimers 4 and 6 as well as (15S)-ethyl-nor-brefeldin A (2) were prepared from the key building blocks 12 or 24 by Julia-Kocienski olefination with tetrazolyl sulfones and subsequent macrolactonization. The vinyl derivative 5 allowed analogues to be synthesized by hydroboration and Suzuki-Miyaura coupling. The following biological properties were assessed: (a) inhibition of cell growth of human cancer cells (NCI), (b) induction of morphological changes of the Golgi apparatus of plant and mammalian cells, and (c) influence on the replication of the enterovirus CVB3. Furthermore, conformational aspects were studied by X-ray crystal structure analysis and molecular mechanics calculations, including docking of the analogues into the brefeldin A binding site of an Arf1/Sec7-complex.