(S)-1-bromooct-1-yn-3-ol | 142748-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-bromooct-1-yn-3-ol
• 英文别名: (3S)-1-bromooct-1-yn-3-ol
• CAS: 142748-76-3
• 化学式: C₈H₁₃BrO
• 分子量: 205.095
• InChiKey: CTUJNCGPJWAYDW-QMMMGPOBSA-N

物化性质

• 沸点：
  242.2±42.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (S)-1-bromooct-1-yn-3-ol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 lithium aluminium tetrahydride 、 三氯化铝 、 二乙胺 作用下， 反应 0.83h， 生成 Methyl (11E,13S)-13-Hydroxyoctadec-11-en-9-ynoate
  参考文献：
  名称：

  Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

  摘要：

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

  DOI：

  10.1016/s0040-4020(01)80454-3
• 作为产物：
  描述：

  [(2S,3S)-3-pentyloxiran-2-yl]methanol 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 lithium amide 、 氨 、 silver nitrate 、 三苯基膦 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 (S)-1-bromooct-1-yn-3-ol
  参考文献：
  名称：

  Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

  摘要：

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

  DOI：

  10.1016/s0040-4020(01)80454-3

文献信息

• Total Synthesis of Thromboxane B₂ via a Key Bicyclic Enal Intermediate
  作者：Changcheng Jing、Varinder K. Aggarwal

  DOI：10.1021/acs.orglett.0c02299

  日期：2020.8.21

  A 12-step asymmetric synthesis of thromboxane B2 (TxB2) from 2,5-dimethoxytetrahydrofuran is described. The synthesis employs our organocatalytic aldol reaction of succinaldehyde to give a key bicyclic enal intermediate. From here, the synthetic strategy involves a conjugate addition of an alkenyl side chain to the bicyclic enal, Baeyer–Villiger oxidation, and a highly Z-selective Wittig olefination

  描述了由2，5-二甲氧基四氢呋喃的12步不对称合成血栓烷B 2（TxB 2）。该合成利用我们的琥珀醛的有机催化醛醇缩合反应生成关键的双环烯醛中间体。从这里开始，合成策略包括将烯基侧链共轭添加到双环烯醛，Baeyer-Villiger氧化和半缩醛的高Z选择性Wittig烯化反应。成功的关键是最大程度地减少氧化还原操作和按正确顺序对官能团进行的操作。
• Saucy–Marbet rearrangements of alkynyl halides in the synthesis of highly enantiomerically enriched allenyl halides
  作者：Yu Tang、Lichun Shen、Becky J. Dellaria、Richard P. Hsung

  DOI：10.1016/j.tetlet.2008.08.089

  日期：2008.11

  A stereospecific Saucy-Marbet rearrangement of alkynyl halides is described here. These rearrangements provide an entry to highly enantiomerically enriched allenyl bromides and chlorides through excellent chirality transfer and the reservation of optical integrity of alkynyl halides.

  这里描述了炔基卤化物的立体特异性 Saucy-Marbet 重排。这些重排通过优异的手性转移和炔基卤化物的光学完整性保留，为高度对映体富集的烯基溴化物和氯化物提供了入口。
• Total Synthesis of (15R)‐ and (15S)‐Prostaglandin A2
  作者：Justus Lackner、Christoph Alberti、Theresa Bock、Katharina Neßmerak、Ernst Urban、Sophia Khom、Nina Schützenmeister

  DOI：10.1002/chem.202401921

  日期：2024.9.5

  Caribbean Vibes in the Lab: Prostaglandin A2 is a tissue hormone, which is also present in Caribbean Sea whips. The short and robust total syntheses of both naturally occurring PGA2 epimers and the subsequent biological evaluation of both compounds revealed an interaction of PGA2 depending on the stereochemistry at C15.

  实验室中的加勒比海氛围：前列腺素 A 2是一种组织激素，也存在于加勒比海鞭子中。两种天然存在的 PGA 2差向异构体的简短而稳健的全合成以及随后对两种化合物的生物学评价揭示了 PGA 2的相互作用取决于 C15 的立体化学。
• Identification of dialkyl diacetylene diols with potent cancer chemopreventive activity
  作者：Chang-Yong Lee、Ji Ho Yun、Kyungsu Kang、Chu-Won Nho、Dongyun Shin

  DOI：10.1016/j.bmcl.2015.05.098

  日期：2015.9

  An increasing importance of chemoprevention for controlling cancer risks prompted the discovery of new active cancer chemopreventive agents. In this study, we designed and synthesized substituted hexa-2,4-diyne-1,6-diols, more structurally simplified, tunable, and easily preparable than natural gymnasterkoreaynes, and evaluated their cancer chemopreventive activities by measuring concentration of doubling quinone reductase activity (CD), cell viability, and chemopreventive index (CI). Most of the diols exhibited good CD activity and low cytotoxicity. In particular, tetradeca-5,7-diyne-4,9-diol and 2-methyltetradeca-5,7-diyne-4,9-diol showed the best cancer chemopreventive activity, approximately equipotent to that of sulforaphane. And, by synthesizing optically active stereoisomers of selected active compounds, the effect of stereochemistry was also studied. Eventually, we produced a chemopreventive compound for in vivo study. (C) 2015 Published by Elsevier Ltd.