(R)-1-bromooct-1-yn-3-ol | 368886-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-bromooct-1-yn-3-ol
• 英文别名: (3R)-1-bromooct-1-yn-3-ol
• CAS: 368886-35-5
• 化学式: C₈H₁₃BrO
• 分子量: 205.095
• InChiKey: CTUJNCGPJWAYDW-MRVPVSSYSA-N

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：

  (R)-1-bromooct-1-yn-3-ol 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 (R)-(E)-1-Bromo-1-octene-3-ol
  参考文献：
  名称：

  Total synthesis of aspirin-triggered 15-epi-lipoxin A4

  摘要：

  The total synthesis of aspirin-triggered 15-epi-LXA(4) has been achieved using a chiral pool strategy for the C1-C12 fragment starting from 2-deoxy-D-ribose. Sharpless catalytic AE generated the C15 chiral center with > 98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu, Ag) in aq. CH3OH at aq. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01187-x
• 作为产物：
  描述：

  1-辛炔-3-醇 在 溴 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 18.5h， 生成 (R)-1-bromooct-1-yn-3-ol
  参考文献：
  名称：

  高选择性锰（I）/路易斯酸使用溴代丙烯烯共催化直接CHH丙炔化反应

  摘要：

  已经开发了具有高选择性的锰（I）/路易斯酸共催化的直接CHH炔丙基化。发现BPh 3不仅可以促进反应性，而且可以提高选择性。可以直接在炔丙基位置上构建仲碳，叔碳，甚至四碳碳中心。内部炔烃和末端炔烃均可轻松获得。手性已成功地从轴向手性异戊烯转移到中心手性。发现该锰催化剂在该反应中的反应性在过渡金属催化剂中是独特的。

  DOI：

  10.1002/anie.201710835

文献信息

• 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。
• 10.1002/chem.202401921
  作者：Lackner, Justus、Alberti, Christoph、Bock, Theresa、Neßmerak, Katharina、Urban, Ernst、Khom, Sophia、Schützenmeister, Nina

  DOI：10.1002/chem.202401921

  日期：——

  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.
• Highly Selective Manganese(I)/Lewis Acid Cocatalyzed Direct C−H Propargylation Using Bromoallenes
  作者：Can Zhu、Jonas Luca Schwarz、Sara Cembellín、Steffen Greßies、Frank Glorius

  DOI：10.1002/anie.201710835

  日期：2018.1.8

  A manganese(I)/Lewis acid cocatalyzed direct C−H propargylation with high selectivity has been developed. BPh3 was discovered to not only promote the reactivity, but also enhance the selectivity. Secondary, tertiary, and even quaternary carbon centers at the propargylic position could be directly constructed. Both internal and terminal alkynes are easily accessible. The chirality was successfully transferred

  已经开发了具有高选择性的锰（I）/路易斯酸共催化的直接CHH炔丙基化。发现BPh 3不仅可以促进反应性，而且可以提高选择性。可以直接在炔丙基位置上构建仲碳，叔碳，甚至四碳碳中心。内部炔烃和末端炔烃均可轻松获得。手性已成功地从轴向手性异戊烯转移到中心手性。发现该锰催化剂在该反应中的反应性在过渡金属催化剂中是独特的。
• Total synthesis of aspirin-triggered 15-epi-lipoxin A4
  作者：Ana R Rodrı́guez、Bernd W Spur

  DOI：10.1016/s0040-4039(01)01187-x

  日期：2001.8

  The total synthesis of aspirin-triggered 15-epi-LXA(4) has been achieved using a chiral pool strategy for the C1-C12 fragment starting from 2-deoxy-D-ribose. Sharpless catalytic AE generated the C15 chiral center with > 98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu, Ag) in aq. CH3OH at aq. (C) 2001 Elsevier Science Ltd. All rights reserved.